Ci a ion: Pé ez-Fe ei o, M.; M.
Abelai as, A.; C iado, A.; Gómez, I.J.;
Mosque a, J. Dend ime s: Explo ing
Thei Wide S uc u al Va ie y and
Applica ions. Polyme s 2023,15, 4369.
h ps://doi.o g/10.3390/
polym15224369
Academic Edi o : Chie Kojima
Recei ed: 14 Sep embe 2023
Re ised: 6 No embe 2023
Accep ed: 7 No embe 2023
Published: 9 No embe 2023
Copy igh : © 2023 by he au ho s.
Licensee MDPI, Basel, Swi ze land.
This a icle is an open access a icle
dis ibu ed unde he e ms and
condi ions o he C ea i e Commons
A ibu ion (CC BY) license (h ps://
c ea i ecommons.o g/licenses/by/
4.0/).
polyme s
Re iew
Dend ime s: Explo ing Thei Wide S uc u al Va ie y
and Applica ions
Ma ía Pé ez-Fe ei o †, Ad ián M. Abelai as †, Alejand o C iado, I. Jénni e Gómez * and Jesús Mosque a *
CICA—Cen o In e disciplina de Química e Bioloxía, Uni e sidade da Co uña, Rúa as Ca ballei as,
15071 A Co uña, Spain
*Co espondence: i.jenni e [email p o ec ed] (I.J.G.); [email p o ec ed] (J.M.)
†These au ho s con ibu ed equally o he wo k.
Abs ac :
Dend ime s cons i u e a dis inc i e ca ego y o syn he ic ma e ials ha bea esemblance
o p o eins in a ious aspec s, such as disc e e s uc u al o ganiza ion, globula mo phology, and
nanoscale dimensions. Rema kably, hese a ibu es coexis wi h he capaci y o acile la ge-scale p o-
duc ion. Due o hese ad an ages, he ealm o dend ime s has unde gone subs an ial ad ancemen
since hei incep ion in he 1980s. Nume ous e iews ha e been dedica ed o elucida ing his subjec
comp ehensi ely, del ing in o he p ope ies and applica ions o quin essen ial dend ime a ie ies
like PAMAM, PPI, and o he s. Ne e heless, he con empo a y landscape o dend ime s anscends
hese ea ly pa adigms, wi nessing he eme gence o a di e se a ay o no el dend i ic a chi ec u es
in ecen yea s. In his e iew, we aim o p esen a comp ehensi e pano ama o he expansi e
domain o dend ime s. As such, ou ocus lies in discussing he key a ibu es and applica ions
o he p edominan ypes o dend ime s exis ing oday. We will commence wi h he con en ional
a ian s and p og essi ely del e in o he mo e pionee ing ones, including Janus, sup amolecula ,
shape-pe sis en , and o axane dend ime s.
Keywo ds:
adi ional dend ime s; Janus dend ime s; sup amolecula dend ime s; shape-pe sis en
dend ime s; o axane dend ime s
1. In oduc ion
Dend ime s a e hype -b anched mac omolecules cha ac e ized by la ge numbe s o
end-g oup unc ionali ies and a compac molecula s uc u e. They consis o a cen al co e
molecule whe e mul iple b anches eme ge, gi ing ise o a hie a chical and well-de ined
a chi ec u e. The b anches consis o epea ed uni s o monome s ha a e chemically linked
oge he in a con olled manne . Since hei in oduc ion in he 80s [
1
], his e olu iona y
class o ma e ials has played a pi o al ole in pushing he bounda ies o polyme chemis y,
e ec i ely b idging he gap be ween syn he ic and biological polyme s. Rema kably,
dend ime s exhibi a ple ho a o excep ional p ope ies ha bea s iking esemblance
o hose o biological mac omolecules, no ably p o eins. These p ope ies encompass
he ollowing:
(i)
Monodispe si y
: Dend ime s can be syn hesized as monodispe sed ma e ials, e-
sul ing in a uni o m and well-de ined molecula weigh dis ibu ion. Dend ime s’
monodispe si y con ibu es o hei unc ionali y and eliabili y in a ious applica ions.
(ii)
Nanome e size
: The size o dend ime s depends on hei gene a ion ( ide in a), bu
in gene al, hey a e se e al nanome e s big, i.e., e y simila o p o eins. This is a
ele an ad an age wi h espec o molecules since a la ge su ace can be applied o
pe o ming mul i alency in e ac ions ha de e mine hei biological beha io .
(iii)
Globula shape
: Dend ime s possess a cha ac e is ic globula shape, which a ises
om hei highly b anched and symme ic s uc u e. This globula a chi ec u e is
c ucial o hei in e ac ions wi h o he molecules.
Polyme s 2023,15, 4369. h ps://doi.o g/10.3390/polym15224369 h ps://www.mdpi.com/jou nal/polyme s
Polyme s 2023,15, 4369 2 o 23
(i )
Adap able su ace
: Dend ime s o e a cus omizable pla o m o he a achmen o
an ex ensi e a ay o molecules. This p ocess o unc ionaliza ion empowe s p ecise
modula ion o hei physicochemical a ibu es and go e ns molecula in e ac ions
anspi ing upon hei su aces.
( )
P esence o ca i ies
: The globula shape o dend ime s c ea es in e nal ca i ies o
oid spaces wi hin hei s uc u e. These ca i ies can accommoda e gues molecules,
d ugs, o o he unc ional moie ies, p o iding a con olled and p o ec ed en i onmen .
The ema kable p ope ies o dend ime s, eminiscen o biological polyme s, ha e
opened up as possibili ies in di e se ields, including nano echnology, medicine, ca alysis,
and ma e ials science. Recen yea s ha e wi nessed he publica ion o a ew e iews
ha ha e ex ensi ely explo ed he p ope ies and applica ions o he mos adi ional
dend ime s [
2
–
5
], i.e., polyamidoamine (PAMAM), poly(p opylene imine) (PPI), polylysine
(PLL), and polyes e dend ime s. In con as , ou e iew aims o dis inguish i sel by
shedding ligh on he eme ging and inno a i e a ian s o dend ime s. Speci ically, ou
s udy is dedica ed o elucida ing he cha ac e is ics and po en ial applica ions o no el
dend ime ypes. By expanding he scope o in o ma ion, we seek o con ibu e o a
comp ehensi e unde s anding o he di e se and e ol ing landscape o dend ime esea ch.
2. Dend ime S uc u e
The physicochemical p ope ies o dend ime s a e de e mined by he h ee cons i uen
pa s: he co e, he b anches, and he end-g oup unc ionali ies. While excep ions exis ,
i is gene ally obse ed ha he co e has a ela i ely lowe impac on p ope ies such as
solubili y, pola i y, o he abili y o he dend ime o in e ac wi h molecules. Howe e ,
besides i s s uc u al ole, he co e molecule can endow he dend ime wi h addi ional
capabili ies. Fo example, po phy ins ha e been applied as dend ime co es, esul ing in
dend ime s wi h luo escence emission and pho osensi izing ea u es [
6
]. Ano he example
is he u iliza ion o cyclophane as he co e, which allows he dend ime o encapsula e
speci ic molecules [7].
On he con a y, he chemical na u e o he b anches signi ican ly in luences he
ollowing dend ime p ope ies:
(i)
Syn hesis
: Di e en ypes o b anches, such as amine-, es e -, o e he -based b anches,
equi e speci ic syn he ic me hodologies o achie e he desi ed dend ime a chi ec u e.
Ca e ul selec ion o b anching uni s allows o p ecise con ol o e dend ime g ow h,
size, gene a ion, and molecula s uc u e.
(ii)
Flexibili y
: B anching uni s g ea ly a ec he igidi y and lexibili y o dend ime s.
Rigid b anches, like a oma ic o bulky g oups, lead o mo e igid dend ime s, while
lexible o alipha ic b anches in oduce g ea e lexibili y [7].
(iii)
Po osi y
: The p ope ies o he b anches impac he accessibili y o molecules o he
dend ime ’s in e io . B anches wi h low solubili y in a sol en can cause dend ime s
o con ac and es ic he sol en ’s accessibili y o he dend ime ’s in e io , also
a ec ing he capabili ies o he dend ime o encapsula e molecules.
(i )
S abili y
: Some b anches ha e chemical g oups ha can be uns able in ce ain condi-
ions, o example, unde hea ing. O he ones, such as es e o amide bonds, can be
b oken by enzymes, making he dend ime biodeg adable.
Finally, he end-g oup unc ionali ies a e he ones loca ed a he ou e mos ends o
he dend ime b anches, and de e mine he su ace p ope ies, eac i i y, and in e ac ions
o he dend ime s wi h o he molecules. They signi ican ly in luence he o e all beha io
o dend ime s, including con ol o e solubili y. By ca e ully selec ing he app op ia e
end-g oups, dend ime s can be ailo ed o exhibi wa e solubili y o solubili y in o ganic
sol en s [
8
]. The ema kable chemical di e si y o end-g oup unc ionali ies allows i -
ually any molecule o be a ached as a e minal g oup, o e ing limi less possibili ies
o cus omizing dend ime s wi h speci ic p ope ies and unc ionali ies. Impo an ly, he
numbe o end-g oup unc ionali ies and he dend ime size is mainly de e mined by
he gene a ion o he dend ime , i.e., he numbe o epea ed b anching cycles ha a e
Polyme s 2023,15, 4369 3 o 23
pe o med du ing i s syn hesis. Each gene a ion adds a laye o b anches, inc easing he
o e all size and he numbe o end-g oup unc ionali ies.
In conclusion, he p ope ies o he dend ime s a e mainly de e mined by (i) he
gene a ion (G1, G2, G3,
. . .
), (ii) he chemical na u e o he b anches, e.g., PAMAM, PPI,
e c., and (iii) he end-g oup unc ionali ies (Figu e 1).
Figu e 1.
Schema ic ep esen a ion o he main pa ame e s ha de e mine he p ope ies o a
dend ime . (Adap ed om Re . [9]).
3. Syn hesis o Dend ime s
Two p ima y app oaches o dend ime o ma ion ha e been de ined: con e gen and
di e gen [
10
]. Each o hese app oaches ca ies unique ad an ages and no able dis inc ions.
The me iculous selec ion o a sui able s a egy s ands as a pi o al ac o , as i will de ine he
dis inc i e cha ac e is ics o he mac omolecule in each scena io.
3.1. Di e gen App oach
This me hodology epo ed by Tomalia e al. [
1
] is based on he s epwise g ow h o
dend ime s, s a ing om a co e con aining di e se binding g oups. Sequen ial eac ions
a e hen pe o med o expand he dend ime o e se e al gene a ions, depending on he
speci ic sequences applied.
These eac ions can in ol e a ious unc ional g oups, such as amines, bo onic acids,
alcohols, among o he s, bu hey all ollow a simila p ocedu e (Figu e 2a). The p ocess
ini ia es wi h a eac ion a he co e, employing non- eac i e unc ional g oups ha appea
Polyme s 2023,15, 4369 4 o 23
a he pe iphe y o he newly o med mac omolecule. Subsequen ly, a dep o ec ion o
ac i a ion s ep is unde aken o con e hese pe iphe al g oups in o eac i e en i ies,
which acili a es he subsequen eac ion. This i e a i e p ocess is epea ed o subsequen
gene a ions un il he inal dend ime is achie ed.
Figu e 2.
Ca oon ep esen a ion o (
a
) di e gen and (
b
) con e gen syn hesis. Rep in ed wi h
pe mission om e . [11]. Copy igh 2019 Ame ican Chemical Socie y.
The main ad an age o his me hodology lies in i s capabili y o gene a e as and
complex s uc u es ia he exponen ial g ow h o he dend ime in each gene a ion. This
p ope y also aids in he pu i ica ion p ocess, as he subs an ial di e ence in size be ween
he dend ime and monome s acili a es hei sepa a ion. Howe e , a signi ican challenge
a ises om he possibili y o side eac ions occu ing in some dend ime s a each s ep. This
is a ibu ed o he inc easing numbe o eac i e g oups wi h each successi e gene a ion.
Consequen ly, he inal yield o each gene a ion is diminished, leading o he o ma ion o
dend ime s wi h s uc u al de ec s due o he p esence o by-p oduc s [12].
To coun e ac he exponen ial inc ease in eac i e g oups and o minimize he o -
ma ion o by-p oduc s, he use o a subs an ial excess o monome s in each s ep o he
app oach is necessa y. This excess ensu es ha he desi ed eac ions a e a o ed and helps
educe unwan ed side eac ions.
3.2. Con e gen App oach
This me hodology, ini ially epo ed by Hawke and F éche in 1990 [
13
], in ol es he
s epwise o ma ion o di e en b anches, known as dend ons, which ul ima ely culmina es
in he syn hesis o he dend ime ’s inal mac os uc u e ia a inal bond wi h he co e.
The syn hesis o hese dend ons ollows a p ocess like he di e gen app oach
(Figu e 2b)
.
The p ima y ad an age o his app oach is he imp o ed con ol o e he dend ime ’s
s uc u e, hanks o he smalle size o he dend ons compa ed o he dend ime i sel . This
necessi a es ewe equi alen s o monome in each syn hesis s ep and a educed o ma ion
o by-p oduc s du ing he eac ions can be obse ed. Enhanced con ol also enables he
p ecise in oduc ion o he desi ed unc ional g oups a he dend ime ’s pe iphe y, which
signi ican ly impac s he inal p ope ies o he mac omolecule [14].
Howe e , a no able d awback is he s e ic hind ance encoun e ed du ing he inal
coupling o he dend ons wi h he co e. The la ge size o he dend ons impedes he eac ion
o o he b anched a ms, limi ing he o ma ion o dend ime s wi h ewe gene a ions
compa ed o he di e gen app oach. Despi e his limi a ion, he con e gen app oach
emains a aluable s a egy o cons uc ing dend ime s wi h con olled s uc u es and
desi able unc ionali ies. I o e s signi ican ad an ages in speci ic applica ions whe e
me iculous con ol and minimized by-p oduc s s and as c ucial conside a ions.
Polyme s 2023,15, 4369 5 o 23
4. T adi ional Dend ime s
Apa om he gene a ion o he dend ime , hei mos common classi ica ion is
based on he chemical na u e o hei b anches. He ein, we de ined adi ional dend ime s
as symme ic mac omolecules o med by a single ype o lexible b anches. Unde his
de ini ion, he mos common dend ime s applied nowadays a e included, o which a b ie
summa y o he main p ope ies is included below.
4.1. PAMAM Dend ime s
These a e comp ised o epea ing uni s o me hyl ac yla e and e hylenediamine; he e-
o e, hey con ain amine and amide g oups in hei in e io . PAMAM was he i s den-
d ime syn hesized and comme cialized. These dend ime s usually ea u e e minal amino
g oups, which con e a ca ionic na u e and ema kable hyd ophilici y. Addi ionally, hose
g oups can be s aigh o wa dly unc ionalized o modula e hei physicochemical p ope -
ies [
15
]. PAMAM inds i s p ima y u ili y wi hin he ealm o biomedical applica ions such
as a gene deli e y uni , an o al d ug deli e y ehicle, o e en an ac i a o o he immune
sys em [
16
]. I is wo h men ioning ha he s abili y o PAMAM dend ime s is ela i ely
lowe in compa ison wi h o he dend ime s. This is a ibu ed o hei suscep ibili y o
e o-Michael eac ions when exposed o high empe a u es, which imposes es ic ions on
hei po en ial applica ions. Re . [
17
] PAMAM syn hesis consis s o pe o ming a Michael
addi ion using a la ge excess o me hyl ac yla e, and subsequen ly, an amida ion eac ion
wi h e hylenediamine.
4.2. PPI Dend ime s
PPI dend ime s a e a dis inc class o dend ime s ha consis s o epea ing p opy-
leneimine uni s. Simila o PAMAM dend ime s, hese dend ime s possess ema kable
hyd ophilici y wi h excellen wa e solubili y due o hei e minal ca ionic amino su ace.
Howe e , hei in e nal pa is mo e hyd ophobic han PAMAM as was shown by using he
sol a och omic p obe phenol blue [
18
,
19
]. This p ope y o PPI dend ime s makes hem
highly desi able o he ask o deli e ing d ugs ha ha e poo solubili y in wa e [
20
].
Mo eo e , PPI dend ime s exhibi high s abili y and can be eadily p epa ed wi h a high
yield, making hem comme cially a ailable. Thei mo e e icien syn hesis consis s o using
a Michael addi ion be ween he p ima y amines and ac yloni ile, and subsequen ly a
he e ogeneous hyd ogena ion wi h a Raney cobal ca alys [21].
4.3. PLL Dend ime s
These a e unique mac omolecules ha a e cons uc ed wi h epea ing L-lysine uni s
linked oge he using amide bonds. The p esence o he asymme ic L-lysine amino acid
impa s chi ali y on he dend ime s uc u e, esul ing in an inhe en ly chi al molecule. Fu -
he mo e, PLL dend ime s exhibi an asymme ical b anching pa e n, whe e he b anches
possess di e en leng hs, con ibu ing o hei complex h ee-dimensional a chi ec u e [
22
].
As in he case o PAMAM and PPI dend ime s, hese dend ime s also possess amino
g oups as end-g oup unc ionali ies, which can be u ilized o enhance hei solubili y in
aqueous as well as o ganic en i onmen s. No ably, an in iguing aspec o PLL dend ime s
is hei biodeg adabili y, owing o hei composi ion based on pep ide bonds. This a ibu e
ende s hem highly sui able o a wide ange o biomedical applica ions, making hem
p omising candida es in he ield [
23
]. In ac , PLL dend ime s a e cu en ly applied in
heal h p oduc s o he ea men and p e en ion o bac e ial aginosis and he p e en ion
o sexually ansmi ed diseases [24].
4.4. Polyes e Dend ime s
These a e a unique class o dend ime s in which he componen s a e linked using
es e bonds. While a ious ypes o polyes e dend ime s ha e been epo ed, hose based
on 2,2-bis(hyd oxyme hyl)p opanoic acid (bis-MPA) a e he mos p e alen . One o he
no able ad an ages o bis-MPA is i s a ailabili y a a low cos , making i an economically
Polyme s 2023,15, 4369 6 o 23
iable op ion. I s p epa a ion consis s o an es e i ica ion in dichlo ome hane wi h he
DCC coupling agen in he p esence o he ca alys DPTS (Figu e 3). Subsequen ly, he
p o ec ion g oup was emo ed easily unde mild condi ions by s i ing he ace onide
de i a i es in MeOH in he p esence o he acidic esin Dowex 50W [
25
]. Nowadays, se e al
companies o e dend ons and dend ime s o bis-MPA, p o iding accessible op ions o
esea che s in e es ed in u ilizing hese s uc u es. Typically, he end-g oup unc ionali ies
o hese dend ime s consis o alcohol moie ies, which o e he e sa ili y o bind o he
unc ionali ies, o en ia he o ma ion o ca bama es [
26
]. Mo eo e , he p esence o
hese alcohol moie ies no only impa s ema kable wa e solubili y bu also o e s he
ad an age o educed oxici y compa ed o he p e ious dend ime s due o hei neu al
cha ge. Impo an ly, MPA dend ime s exhibi supe io biodeg adabili y compa ed o PLL
polyme s, p ima ily due o he lowe s abili y o es e bonds in compa ison o amide bonds.
Fo his eason, hey a e ex ensi ely applied in biological applica ions [27].
Figu e 3.
Syn hesis o a G3 bis-MPA dend ime . DCC is he coupling agen
N,N
0
-dicyclohexylca bodiimide and DPTS is he molecule 4-(dime hylamino)py idinium 4-
oluenesul ona e ha ac s as he ca alys .
4.5. Polye he Dend ime s
These a e ano he ype o dend ime closely ela ed o polyes e dend ime s. The
key dis inc ion be ween hese wo amilies lies in hei chemical bonds, as polye he
dend ime s a e bound using es e bonds. This di e ence in bonding gi es polye he
dend ime s a signi ican ad an age in e ms o s abili y compa ed o polyes e dend ime s,
pa icula ly when i comes o chemical and biological deg ada ion. Among he polye he
dend ime s, poly(benzyl e he ) dend ime s s and ou as he mos ep esen a i e polye he
dend ime [
28
]. A key cha ac e is ic o his dend ime is ha hei b anch s uc u e is qui e
hyd ophobic [29].
4.6. O ganoelemen Dend ime s
O ganoelemen dend ime s e e o a class o dend i ic mac omolecules cha ac e ized
by he inco po a ion o non-ca bon elemen s, such as silicon [
30
], phospho us [
31
], and
bo on [
32
], in o hei cen al co e s uc u e. Among o ganoelemen dend ime s, hose
con aining silicon, such as ca bosilane and ca bosiloxane dend ime s [
30
,
33
], a e o en
highly ep esen a i e. One key ad an age o silicon-con aining dend ime s is hei ease
o syn hesis, coupled wi h hei excep ional chemical s uc u e, ea u ing obus Si–C
bonds [
34
]. These Si–C bonds a e no easily b oken o a ec ed by unwan ed o side
chemical eac ions du ing hei p epa a ion, making hei p oduc ion simple .
Polyme s 2023,15, 4369 7 o 23
4.7. Applica ions o T adi ional Dend ime s
T adi ional dend ime s ha e ound applica ions in a wide ange o ields due o hei
unique p ope ies and e sa ile s uc u es [
35
]. Howe e , a signi ican ocus is placed
on explo ing hei po en ial applica ions in he ield o biomedicine, he main ones being
he ollowing:
(i)
MRI con as agen s
: Since he sensi i i y o magne ic esonance imaging (MRI) o
issue ype di e ences is ela i ely low, pa amagne ic me als a e used as con as
agen s. These agen s a e used o sho en he elaxa ion imes o he su ounding wa e
p o ons in o de o imp o e con as . To minimize he need o high doses o con as
agen , dend ime s ha e been deco a ed wi h coo dina ing g oups o endow a ini y
o me als like gadolinium. This s a egy allows us o inc ease he e iciency o he
con as agen and also modi y i s biodis ibu ion [
36
]. None heless, me als end o
exhibi oxici y; hence, esea che s a e cu en ly in es iga ing a p ospec i e class o
con as agen s. These agen s ely on dend ime s ado ned wi h unc ional o ganic
adicals, showing p omising po en ial as MRI con as agen s [37].
(ii)
Tissue enginee ing
: Since dend ime s can be modi ied o inco po a e o encapsula e
a a ie y o biological and/o chemical subs ances, hey ha e been used in issue
enginee ing o design a i icial ex acellula ma ices. Fo ins ance, dend ime s can be
applied o encapsula e g ow h ac o s and elease he componen s in he na i e ex a-
cellula ma ix in a con olled manne o enable issue egene a ion. Ano he op ion
is o use dend ime s o o m hyd ogels ha mimic na u al ex acellula ma ices o
induce he g ow h o he seeded cells [38].
(iii)
Gene deli e y
: Dend ime s can be applied as a non- i al gene deli e y pla o m.
In pa icula , PAMAM and lysine-based dend ime s ha e shown a ini y o DNA
molecules inducing he o ma ion o dend iplexes (i.e., complex ob ained a e he
elec os a ic in e ac ion be ween dend ime s and nucleic acids). These s uc u es
enhance he cellula up ake o DNA ia a ious mechanisms, such as endocy osis.
Addi ionally, a e cellula up ake, he dend iplex acili a es he escape o cells, which
a e o en apped in endosomes, in o he cy oplasm [39].
(i )
D ug deli e y sys ems
: Dend ime s o d ug deli e y can be used in wo di e en
ways: o mula ion whe e hey a e en apped in a dend ime using non-co alen
in e ac ions, and nanocons uc ion whe e d ugs a e co alen ly coupled on dend ime s.
Bo h s a egies allow us o inc ease he solubili y, s abili y, and o al bioa ailabili y o
a ious d ugs [40].
5. Janus Dend ime s
Janus pa icles, named a e he wo- aced Roman god Janus, a e used o desc ibe
a unique class o pa icles ha ha e wo dis inc sides ha can be aniso opic in hei
composi ion and su ace ea u es. Janus pa icles ha e ecei ed a conside able amoun
o in e es ecen ly as nex -gene a ion “sma ” nanoma e ials. They p o ide asymme y
and can hus impa d as ically di e en chemical o physical p ope ies and di ec ionali y
wi hin a single pa icle [
41
]. B oken symme y o e s an e icien and dis inc i e means o
a ge complex sel -assembled ma e ials and ealize he eme gence o p ope ies (p esen ly)
inconcei able o homogeneous pa icles.
Rega ding Janus dend ime s, he e a e wo possible ypes o hese dend ime s. The
i s and mo e common ype is cha ac e ized by ha ing di e en end-g oup unc ionali ies
and dis inc b anch s uc u es in each pa . The second ype is cha ac e ized by ha ing
only di e en end-g oup unc ionali ies while main aining simila b anch s uc u es. The
mos common me hod o p epa e bo h ypes o dend ime s in ol es he eac ion o dis inc
dend ons possessing complemen a y unc ions [
42
]. This app oach u ilizes a con e gen
syn hesis s a egy, whe e he dend ons a e indi idually syn hesized and subsequen ly
connec ed o each o he using a ious eac ions, such as “click chemis y”. Al e na i ely,
ano he app oach in ol es he u iliza ion o mul i- unc ional co es, which enable he
Polyme s 2023,15, 4369 8 o 23
execu ion o wo dis inc di e gen syn heses o gene a e he wo dis inc pa s o he Janus
dend ime [43,44].
One o he mos in e es ing p ope ies o Janus dend ime s a e hei sel -assembly
capabili ies in wa e when hey combine a hyd ophilic and ano he hyd ophobic pa .
Re olu iona y esea ch published in 2010 led by Vi gil Pe cec showed ha amphiphilic
Janus dend ime s can sel -assemble in wa e , o ming s able bilaye esicles e e ed o
as dend ime somes (Figu e 4) [
45
]. In his wo k, he au ho syn hesized a lib a y o 107
amphiphilic Janus dend ime s by combining wo hyd ophobic segmen s (one alipha ic and
one mixed alipha ic-a oma ic) and six hyd ophilic segmen s de i ed om oligoe hylene
oxide, dime hylolp opionic acid, glyce ol, hioglyce ol, e -bu ylca bama e, and qua e na y
ammonium sal s. The sel -assembly p ope ies o hese dend ime s we e s udied using
c yo-TEM, which showed a ich pale e o mo phologies in wa e , including esicles,
cubosomes, disks, ubula esicles, and helical ibbons. Impo an ly, dend ime somes can
also inco po a e po e- o ming p o eins, coassemble wi h s uc u e-di ec ing phospholipids
and block co-polyme s, and o e a molecula pe iphe y sui able o u he chemical
unc ionaliza ion.
Figu e 4.
(
a
) Schema ic ep esen a ion o he dend ime somes based on ionizable amphiphilic Janus
dend ime s (IAJD) de eloped by Pe cec’s g oup o he encapsula ion o mRNA. (
b
) Chemical
s uc u e o a ypical IAJD. Rep in ed wi h pe mission om e . [
46
]. Copy igh 2021 Ame ican
Chemical Socie y.
Fo he syn hesis o he o me Janus dend ime s, V. Pe cec and cowo ke s de eloped
a syn he ic s a egy known as he modula -o hogonal me hodology [
47
]. This app oach
in ol es using a e a- unc ional co e, i.e., pen ae y h i ol, as a co e molecule, in conjunc ion
wi h o hogonal-p o ec ing g oups. The p o ec ing g oups enable he co e o be di e en-
ially subs i u ed, ul ima ely esul ing in he o ma ion o a ype o Janus dend ime s called
win- win dend ime s, which usually comp ise wo iden ical hyd ophobic dend ons and
wo iden ical hyd ophilic dend ons. Fu he mo e, his me hodology was imp o ed by in-
co po a ing is(hyd oxyme hyl)aminome hane as he co e molecule, enabling he syn hesis
o dend ime s wi h h ee dis inc egions [
46
]. Te med hyb id win-mix dend ime s, hese
s uc u es consis o wo iden ical hyd ophobic dend ons and wo di e en hyd ophilic
dend ons (Figu e 4b). Pe cel’s g oup has success ully exploi ed hese syn he ic s a egies o
ob ain a wide ange o dend ime s, opening up possibili ies o a ious applica ions. Some
o he no able applica ions include:
(i) RNA deli e y: E icien deli e y o nucleic acids is he key s ep o gene ic nanomedicine.
Pe cec’s g oup applied he modula -o hogonal me hodology o de elop a lib a y
o 54 amphiphilic Janus dend ime s con aining ionizable amines o pe o m mRNA
deli e y
in i o
(Figu e 4) [
46
]. These Janus dend ime s can encapsula e la ge quan-
i ies o mRNA a an acidic pH (pH 3 o 5), when he amino g oups a e p o ona ed,
due o he elec os a ic in e ac ions. In con as o common lipid nanopa icles ha
equi e complex mic o luidic echnology o encapsula e RNA, hese dend ime somes
pe o m he encapsula ion ia simple injec ion, and allow long- e m s o age.
(ii)
Killing o bac e ia: An ibio ic esis ance is a se ious global heal h p oblem necessi a -
ing new bac e icidal app oaches such as nanomedicines. Molly M. S e ens’ g oup
has aken ad an age o he syn he ic s a egy de eloped by Pe cel’s g oup o he
syn hesis o Janus dend ime s o design a dend ime some-based nano eac o , wi h
Polyme s 2023,15, 4369 9 o 23
b oad-spec um bac e icidal ac i i y [
48
]. This nano eac o consis s o a dend ime -
some wi h a semipe meable memb ane whe e wo enzymes, namely glucose oxidase
(GOx) and myelope oxidase (MPO), a e encapsula ed. Via ex e nal addi ion o glucose
o his sys em, hypochlo i e, which is a highly po en an imic obial, is p oduced by
he enzyma ic cascade. This cascade nano eac o yielded a po en bac e icidal e ec
agains wo impo an mul id ug esis an pa hogens, S aphylococcus au eus (S. au eus)
and Pseudomonas ae uginosa (P. ae uginosa).
(iii)
Building mimics o cell memb anes: The glycocalyx is he i s componen o he cell
ha in e ac s wi h he en i onmen , enabling cell communica ion, cell adhesion, and
so on. Impo an ly, he glycan moie ies a he cellula memb ane ha e speci ic spa ial
a angemen s ha can be exploi ed by some pa hogenic bac e ia and i uses o a ack
cells. S udying na u al glycocalyx is impo an o de elop syn he ic models o dissec
s uc u e– unc ion ela ions. To his end, a ype o amphiphilic Janus dend ime s
con aining ca bohyd a es in he hyd ophilic pa has been de eloped, namely gly-
codend ime s [
47
]. The glycodend ime somes de i ed om hese dend ime s ha e
been shown o mimic some o he sup amolecula o ganiza ion o na u al memb anes.
Fo example, i was demons a ed ha using glycodend ime somes deco a ed wi h
mannose, he suga moie ies we e o ganized in o pe iodic nanoa ays wi hou he
need o he o ma ion o liquid-o de ed phases as assumed necessa y o a s.
A simila example was de eloped by he g oup o Guang Yang [
49
]. They designed a
amily o dynamic amphiphilic Janus glycopep ide dend ime s con aining a
β
-cyclodex in
as he co e and 14 saccha ide dend ons as he hyd ophilic pa . Addi ionally, hey also had
se en pep ide a ms as he hyd ophobic egion, which we e bonded o he co e using acylhy-
d azone bonds. These dend ime s we e sel -assembled in o di e en glyco-nanos uc u es
wi h con ollable mo phologies including glycosphe es, wo m-like micelles, and ibe s.
Fu he mo e, disassembly could be induced using he addi ion o an acid ha hyd olyzes
acylhyd azone bonds; hus, hey could be applied o he a ge ing and con ollable elease
o encapsula ed gues ca gos.
6. Sup amolecula Dend ime s
Sup amolecula dend ime s a e a class o highly b anched mac omolecules o med
ia he sel -assembly o epea ing subuni s, known as dend ons [
50
]. Unlike adi ional
dend ime s, which ely on co alen bonds, hese a e held oge he and s abilized using
e e sible non-co alen in e ac ions, such as hyd ogen bonding, elec os a ic,
π−π
, o
me al–ligand in e ac ions [
51
,
52
]. The dynamic beha io o he physicochemical p op-
e ies asc ibed o non-co alen in e ac ions can be e e sible, enabling sup amolecula
dend ime s o exhibi esponsi eness o a ious ex e nal s imuli, such as changes in pH,
empe a u e, and/o he p esence o speci ic molecules [
53
]. Some o he key p ope ies and
ad an ages o sup amolecula dend ime s, in con as o co alen ly bonded dend ime s,
a e as ollows: easy modi ica ion due o he accessible unc ional g oups on hei pe iphe y,
and he e e sibili y and unabili y o hei dend ime s uc u e.
While he o ma ion o adi ional dend ime s su e s om ime-consuming p oce-
du es and low yields due o s e ic conges ion, he sel -assembly p oduc ion o sup amolec-
ula dend ime s o e s conside able ad an ages: simple p ocesses, as and e ec i e
c ea ion o he inal p oduc , and inhe en ly de ec - ee assembly [
54
]. The syn hesis o
sup amolecula dend ime s can be achie ed using cus om-designed s a egies and mod-
i ica ions o ailo he dend i ic s uc u es and p ope ies acco ding o speci ic needs, as
discussed p e iously. One o he mos impo an syn he ic s eps esides wi h he selec-
ion o he app op ia e building blocks, including a dend i ic co e, pe iphe al unc ional
g oups, and las ly a linke molecule, which will p o ide he complemen a y unc ionali ies
o sel -assembly [
54
]. Sup amolecula dend ime s can be classi ied based on he ype
o non-co alen in e ac ions ha occu be ween he dend ime componen s in o h ee
main classes.
Polyme s 2023,15, 4369 16 o 23
Figu e 10.
Rep esen a ion o ype I-C o axane dend ime syn hesized using he slippage me hodol-
ogy. Rep in ed wi h pe mission om e . [86]. Copy igh 2002 Ame ican Chemical Socie y.
8.2. Type II Ro axane Dend ime s
Type II dend ime s e e o dend ime s ha possess a pe iphe y ado ned wi h o-
axane s uc u es. Howe e , in con as o ype I, hese dend ime s a e ypically based
on pseudo o axanes ins ead o o axane. A pseudo o axane is a ype o o axane ha
lacks bulky g oups a he ends; he eby, i can be dissocia ed in o i s wo componen s
wi hou b eaking he co alen bonds [
87
]. Like ype I RDs, hese dend ime s can also be
ca ego ized in o sub ypes A, B, and C, al hough ype II-A is he mos abundan class by a .
The mos ypical examples o his ype o pseudo o axane- e mina ed dend ime a ailable
in he li e a u e exploi he hos –gues in e ac ions o cyclodex ins (CDs, Figu e 11a) o
cucu bi u ils (CBs) [
88
,
89
]. Rema kably, he p esence o CDs in he dend ime b anches
enhances hei solubili y in wa e [90].
In ecen yea s, se e al examples o ype II-A ha e been epo ed ha a e based on
o axanes ins ead o pseudo o axanes. O he sup amolecula hos s di e en om CB and
CD uni s ha e been used. Fo ins ance, Qu e al. in oduced a s aigh o wa d syn he ic
app oach ia he Co-ca alyzed [2+2+2] alkyne cyclo ime iza ion p ocess ha allowed hem
o ans o m a [3] o axane (i.e., he numbe in b acke s indica es he numbe o componen s
o he o axane) based on a c own e he in o a hexa-b anched [7] o axane in a single
s ep [
92
]. On he o he hand, Goldup and colleagues ook ad an age o he Cu-media ed
azide–alkyne cycloaddi ion (CuAAC) o syn hesize in e locked iazole unc ionalized
po phy inoids wi h an excellen yield [93].
Polyme s 2023,15, 4369 17 o 23
Figu e 11.
Rep esen a ions o o axane dend ime s: (
a
) s uc u e o a ype II o axane dend ime .
He e, he dend ime se es as a h ee-dimensional empla e o o ganize CD ecep o s in he pe iphe y.
(
b
) Type III o axane dend ime s o gene a ion 2 (G2). Adap ed om e s. [
89
,
91
]. Copy igh 1997
Ame ican Chemical Socie y and 2018 Sp inge Na u e.
8.3. Type III Ro axane Dend ime s
These a e dend i ic poly o axanes whose o axane uni s o m pa o he dend ime
b anches and a e also e e ed o as o axane-b anched dend ime s. The i s example o
his ype o dend ime was epo ed by S odda e al. in 1995 [
94
]. They success ully
syn hesized a G1, ype III-A dend ime con aining [4] o axane by means o a slippage
p ocedu e. In 2013, Leung e al. desc ibed he syn hesis and cha ac e iza ion o ype
III-B o axane dend ime s, speci ically a G1 [3] o axane dend ime and a G2 [4] o axane
dend ime [95].
High-gene a ion ype III dend ime s s and ou as one o he mos in e es ing ypes
o dend ime s wi hin he domain o dend i ic s uc u es. No ably, he augmen a ion in
dend ime gene a ion yields an exponen ial inc ease in he numbe o o axanes wi hin his
dend i ic ype. Consequen ly, ha nessing he s imulus- esponsi e a ibu es o o axanes
enables he concep ualiza ion o sophis ica ed RDs ha exhibi p o ound al e a ions in
dimensions upon exposu e o speci ic s imuli. Fo he p epa a ion o hese dend ime s, he
Leung g oup published in 2018 he syn hesis o a ully o ganic ype o III-B RD o up o
G4 gene a ion ia a con e gen pa hway using a CuAAC eac ion (Figu e 11b) [
91
]. On
he o he hand, he H. Yang g oup de eloped ano he s a egy o syn hesize G4 RDs based
on pla inum
−
ace ylide moie ies, whe e hese moie ies se ed as bo h bulky s oppe s o
p e en de h eading and a eac i e si e ha could be used o g ow he dend ime s. Using
his syn he ic app oach, hey p epa ed bo h G4 dend ime s o ype III-A and ype III-C [
83
].
8.4. Applica ions o Ro axane Dend ime s
Ro axane dend ime s ind a wide a ay o applica ions, including bu no limi ed o:
(i)
Molecula machines:
Se e al o he p e iously men ioned RDs exhibi esponsi e
beha io ha can be egula ed by ex e nal ac o s such as pH, edox condi ions,
ligh exposu e, al e a ions in sol en s, and he in oduc ion o anions. This inhe en
s imulus esponsi eness leads o modi ica ions in hei dimensions, a ising om a co-
o dina ed expansion–con ac ion mo emen wi hin he in eg a ed o axane-b anched
dend i ic s uc u e. Impo an ly, hese s uc u es hold g ea p omise o he de elop-
men o unc ional uni s ha enable con olled elease o subs ances in d ug deli e y
Polyme s 2023,15, 4369 18 o 23
sys ems [
96
]. Beyond his applica ion, he design o a i icial muscles s ands ou
as ano he exci ing p ospec , wi h he po en ial o ansduce chemical ene gy in o
mechanical ene gy [
87
]. To op imize his dis inc i e size al e a ion phenomenon, i is
impe a i e o he dend ime s o ha bo he maximum possible coun o o axanes.
Consequen ly, he mos p omising con ende s o he de elopmen o molecula ma-
chine y applica ions a e he high-gene a ion ype III RDs [
96
]. This ac was clea ly
exempli ied by a wo k published by Yang’s g oup. They desc ibed he syn hesis o
ype III-C RDs, including G1, G2, G3, and G4, by employing he pla inum–ace ylide
me hodology as p e iously discussed. These syn hesized dend ime s unde go an
expansion–con ac ion dynamic in esponse o he p esence o absence o ace a e
anions, esul ing in a e e sible modula ion o hei sizes wi hin o ganic sol en s. The
assessmen o hese RDs’ swelling a ios using 2-D DOSY expe imen s e ealed he
ollowing esul s: 22.9% o G1, 28.8% o G2, 34.7% o G3, and 38.3% o G4. This
illus a ed a clea p og ession as a unc ion o he dend ime gene a ion [97].
(ii)
Ligh ha es ing:
Pho osensi ize s play a signi ican ole in ligh ha es ing, which
is he p ocess o cap u ing and con e ing ligh ene gy in o ano he o m o ene gy,
such as chemical ene gy o elec ical ene gy. In his con ex , o axane dend ime s wi h
applica ions as pho osensi ize s we e designed. The non-co alen modi ica ion o
dend ime pe iphe ies o e s bene i s such as e e sibili y, selec i i y, and adjus abili y,
use ul o p e en unwan ed in e ac ions be ween pe iphe al ch omopho es, which
would cause ene gy loss du ing he p ocess [98,99].
9. Conclusions and Fu u e Pe spec i es
Since he i s example o a dend ime was published in he 80s [
1
], he ield o den-
d ime s has expe ienced signi ican ad ancemen s, leading o a wide a ay o a ailable
dend ime s oday. Fo example, only conside ing he classical dend ime s, he e is a e-
ma kable di e si y in e ms o hei s abili y and pola i y. Equally, some exhibi excep ional
s abili y, ensu ing hei longe i y and esis ance o deg ada ion (e.g., PPI), while o he s
a e designed o be biodeg adable, allowing o con olled b eakdown o e ime (bis-MPA
dend ime s) [27].
Beyond he classical dend ime s, he ield has wi nessed he eme gence o exci ing
dend ime a chi ec u es ha g ea ly expand he po en ial applica ions and capabili ies
o hese nanoscale s uc u es. One ema kable b eak h ough in ecen yea s has been he
syne gis ic in e ac ion be ween molecula sel -assembly and dend ime s. This in e ac ion
has pa ed he way o he de elopmen o no el ypes o dend ime s wi h unp eceden ed
p ope ies. Fo ins ance, sup amolecula dend ime s ha e been designed, le e aging
he sel -assembly o molecula componen s o o m in ica e and highly o ganized s uc-
u es [
54
]. Ano he ema kable ad ancemen is he de elopmen o o axane-b anched
dend ime s, which combine he con olled b anching o adi ional dend ime s wi h he
mechanically in e locked a chi ec u e o o axanes [
96
]. Mo eo e , his syne gy has also
led o he design o no el sel -assembled sys ems whe e dend ime s a e used as building-
blocks, e.g., dend ime somes [
45
]. These s uc u es mimic na u al cell memb anes and hold
g ea po en ial o applica ions in d ug deli e y, nano eac o s, and bioma e ials. Ce ainly,
he combina ion o molecula sel -assembly and dend ime s holds emendous p omise o
he c ea ion o highly unc ional ma e ials in he nea u u e.
Howe e , despi e he emendous ad ance in he dend ime ield, he e a e s ill wo
challenges ha limi he applica ion o hese ma e ials.
(i)
Syn he ic limi a ions
: The syn he ic me hodology o adi ional dend ime s has
unde gone signi ican ad ancemen s. Fo ins ance, a ecen syn he ic p o ocol enables
he apid p epa a ion o G5 dend ime s wi hin a span o less han 12 h [
100
]. Howe e ,
a no able challenge emains in achie ing high yields and monodispe si y in he
syn hesis o high-gene a ion dend ime s. Di e gen syn hesis yields high-gene a ion
dend ime s wi h inc eased yields bu comp omised b anching accu acy. Con e sely,
he con e gen syn hesis app oach gene a es monodispe se ma e ials; howe e , i
Polyme s 2023,15, 4369 19 o 23
su e s om diminished yields, and is inadequa e o p oducing high-gene a ion
dend ime s due o he s e ic hind ance be ween he dend ons. P esen ly, he mos
a o able s a egies o syn hesizing high-gene a ion dend ime s p edominan ly ely
on click chemis y eac ions, pa icula ly alkyne–azide cycloaddi ion, chosen o i s
no able e iciency [
101
]. Fu he mo e, a ious esea ch g oups ha e endea o ed
o add ess he a o emen ioned challenges by employing solid-phase syn hesis as a
me hod o dend ime p epa a ion. I is impo an o no e ha , despi e hese e o s,
his echnology is s ill limi ed o low-gene a ion dend ime s a he millig am o g am
scales [102].
(ii)
P epa a ion o mul i unc ional dend ime s
: As was s a ed in he in oduc ion, den-
d ime s and p o eins sha e se e al p ope ies in common. Howe e , a c ucial dis-
inc ion eme ges in ha while p o eins exhibi ema kable asymme y and highly
p ecise a angemen s o unc ionali ies, dend ime s a e cha ac e ized by ema kable
symme y, o en showcasing a singula ype o unc ionali y. Al hough e o s ha e
been made o design mul i unc ional dend ime s, hese ma e ials cu en ly exhibi
a andom dis ibu ion o such unc ionali ies [
103
]. Undoub edly, he syn hesis o
dend ime s inco po a ing mul i unc ional a angemen s on hei su aces is poised o
inaugu a e a new ealm o highly unc ional syn he ic ma e ials.
A no ewo hy de elopmen in he ealm o dend ime s is he eme gence o ec o-
dend ime s, o en e e ed o as megame s [
104
]. Tec o-dend ime s ep esen a no el
app oach, whe e dend ime s se e as eac i e modules o cons uc ing nanoa chi ec u es
o g ea e complexi y and la ge dimensions. One p ominen a chi ec u al con igu a ion
achie ed using his app oach in ol es he assembly o shell-like s uc u es composed
o wo dis inc dend ime ypes. To da e, hese a chi ec u es ha e been mainly applied
as con as agen s o he magne ic esonance imaging o umo s [
105
,
106
], and as gene
deli e y pla o ms [107].
This inno a i e usion o ad anced syn he ic echniques, enabling he c ea ion o
mul i unc ional dend ime s wi h he concep o ec o-dend ime s, holds immense p omise
o he u u e. I opens he doo o he de elopmen o in ica e hie a chical s uc u es
wi h he po en ial o pe o m sophis ica ed unc ions, pe haps e en mi o ing biological
sys ems.
Au ho Con ibu ions:
Concep ualiza ion, I.J.G. and J.M.; w i ing—o iginal d a p epa a ion,
M.P.-F.
, A.M.A., I.J.G. and J.M.; w i ing— e iew and edi ing, A.C., I.J.G. and J.M.; supe ision,
A.C., I.J.G. and J.M.; unding acquisi ion, A.C. and J.M. All au ho s ha e ead and ag eed o he
published e sion o he manusc ip .
Funding:
J.M. acknowledges Xun a de Galicia o i s esea ch g an P oxec os de Excelencia (No.
ED431F 2022/02) and RYC2019-027842-I om MCIN/AEI/ 10.13039/501100011033 and “ESF: In-
es ing in You Fu u e”. I.J.G. acknowledges he Spanish Minis y o Uni e si ies o a Bea iz
Galindo (BG22/000147) and Ma ia Zamb ano g an (RSU.UDC.MZ09) ans e ed by he Eu opean
Union’s Nex Gene a ionEU. A.C. acknowledges inancial suppo om g an s RYC2020-030183-I
and PID2021-127002NA-I00, unded by MCIN/AEI/ 10.13039/501100011033 and “ESF: In es ing in
You Fu u e”.
Ins i u ional Re iew Boa d S a emen : No applicable.
In o med Consen S a emen : No applicable.
Da a A ailabili y S a emen : No applicable.
Con lic s o In e es : The au ho s decla e no con lic o in e es .
Re e ences
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