Sci 2019, 1, 13; doi: 10.3390/sci1010013. 1 www.mdpi.com/jou nal/sci
A icle
Syn hesis, S uc u al Cha ac e iza ion, and Biological
Ac i i ies o O ganically Templa ed Cobal
Phosphi e (C4N2H14)Co(H2PO3)4·2H2O
Najlaa Hamdi 1, Souad Chaouch 1, I an da Sil a 2, Mohamed Ezah i 3, Mohammed Lachka 1,
Rama Alhasan 4, Ahmad Yaman Abdin 4, Claus Jacob 4 and B ahim El Bali 1
1 Enginee ing Labo a o y o O ganome allic and Molecula Ma e ials, Facul y o Sciences,
Uni e si y Sidi Mohamed Ben Abdellah, Po. Box 1796 (A las), 30000 Fez, Mo occo;
[email p o ec ed] (N.H.); chaouc[email p o ec ed] (S.C.); [email p o ec ed]om (M.L.);
[email p o ec ed] (B.E.B.)
2 ISIS Facili y, STFC Ru he o d Apple on Labo a o y, Chil on, Ox o dshi e OX11 0QX, UK;
[email p o ec ed]
3 Labo a oi e Ma é iaux e En i onnemen , Facul é des Sciences, Uni e si é Ibn Zoh , B.P. 8106,
Ci é Dakhla, 80000 Agadi , Ma oc; m.eza[email p o ec ed]
4 Depa men o Pha macy, Building B 2.1, Room 1.13, Saa land S a e Uni e si y, Saa b uecken, Ge many;
[email p o ec ed]-saa land.de (R.A.); yaman.ab@ho mail.com (A.Y.A.); [email protected] land.de (C.J.)
* Co espondence: [email protected]
Recei ed: 17 Janua y 2019; Accep ed: 5 Ma ch 2019; Published: 12 Ma ch 2019 (Ve sion 1, doi:
10.3390/sci1010013. 1)
Abs ac : A no el hyb id phosphi e [(C4N2H14)Co(H2PO3)4·2H2O] was syn hesized wi h 1,4-
diaminobu ane (dabn) as a s uc u e-di ec ing agen using slow e apo a ion me hod. Single c ys al
X- ay di ac ion analysis showed ha i c ys allizes in he iclinic sys em (S.G: P-1, #2) wi h he
ollowing uni cell pa ame e s (Å, °) a = 5.4814 (3), b = 7.5515 (4), c = 10.8548 (6), α = 88.001 (4), β =
88.707 (5), γ = 85.126 (5). The c ys al s uc u e was buil up om co ne -sha ing [CoO6]-oc ahed ons,
o ming chains pa allel o [001], which a e in e connec ed by H2PO3 pseudo-py amid uni s. The
dip o ona ed 1,4-diaminobu ane molecules, esiding be ween he pa allel chains, in e ac ed wi h
he ino ganic moie y ia hyd ogen bonds leading hus o he o ma ion o he 3D c ys al s uc u e.
The Fou ie ans o m in a ed esul exhibi ed cha ac e is ic bands co esponding o he phosphi e
g oup and he o ganic molecule. The he mal decomposi ion o he compound consis s mainly o
he loss o he o ganic moie y and he wa e molecules. The biological es s exhibi ed signi ican
ac i i y agains Candida albicans and Esche ichia coli s ains in all used concen a ions, while less
ac i i y was p onounced when es ed agains S aphylococcus epide midis and Saccha omyces ce e isiae,
while he e was no ac i i y agains he nema ode model S eine nema el iae.
Keywo ds: hyb id phosphi e; c ys al s uc u e; he mal beha io ; biological ac i i ies; an imic obial;
mic o-o ganisms
1. In oduc ion
Hyb id o ganic-ino ganic ma e ials ha e a ac ed a g ea deal o a en ion in di e en ields
because o hei ich s uc u al chemis y and wide po en ial applica ions in ion-exchange, adso p ion,
sepa a ion, and ca alysis [1–7]. Wi hin his class o s uc u es, hyb id phosphi e con inues o a ac
in ense esea ch a en ion om all ace s o ma e ial scien is s since i p omo ed he o ma ion o a
new ange o s uc u es wi h a ious a chi ec u es and dimensionali y [8]. These ma e ials migh
exhibi di e en ypes: simple (single me al) [9–12], mixed-me al [13–20] o hyb id (o ganic-ino ganic)
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[21,22]. In his con ex , we ha e desc ibed in he p esen pape he syn hesis, c ys al s uc u e,
spec oscopic cha ac e iza ion, and he mal beha io o he new hyb id phosphi e
[(C4N2H14)Co(H2PO3)4·2H2O]. Mo eo e , we ha e epo ed on he biological ac i i ies, ha is, i s
ac i i y agains C. albicans, E. coli s ains, S. epide midis, and S. ce e isiae as a i s con ibu ion in he
in es iga ions conduc ed by ou esea ch g oup on such esea ch in he ield o phosphi e-phospha e
ma e ials.
2. Expe imen al
2.1. Syn hesis
Single c ys als o [(C4N2H14)Co(H2PO3)4·2H2O] we e syn hesized unde ambien condi ions. The
eac ion mix u e o Co(NO3)2·6H2O (1 mmol, 300 mg), 1,4-diaminobu ane (dabn) (2 mmol, 170 mg),
and H3PO3 (4 mmol, 300 mg) was shaken in dis illed wa e o 6 h and hen le a oom empe a u e.
A e wo weeks, he pink solu ion had concen a ed and hexagonal pu ple c ys als, which we e
ha es ed washed wi h he wa e -e hanol mix u e (80:20) and d ied in ai .
2.2. Ma e ials and Ins umen a ion
All eagen s we e acqui ed om comme cial sou ces and used wi hou u he pu i ica ion. The
in a ed spec um o he compound was eco ded on a VERTEX 70 FTIR Spec ome e in he ange
4000–400 cm−1 using he ATR echnique a 4 cm−1 esolu ion. The mog a ime ic analysis (TGA) da a
we e eco ded on an SDT-Q600 analyze om TA Ins umen s (Eschbo n, Ge many). The
empe a u e a ied om RT o 1173 K a a hea ing a e o 10°/min−1. Measu emen s we e ca ied ou
on samples in open pla inum c ucibles unde ai low.
2.3. C ys al S uc u e De e mina ion
C ys al S uc u e De e mina ion
Single-c ys al X- ay di ac ion measu emen was ca ied ou a oom empe a u e using an
Agilen Gemini S di ac ome e equipped wi h a CCD de ec o and molybdenum (Mo) adia ion
sou ce. Acqui ed da a we e p ocessed wi h he C ysAlisP o so wa e [23]. Using Olex2 [24], he
s uc u e was sol ed wi h he olex2.sol e [25] s uc u e solu ion p og am using Cha ge Flipping and
e ined wi h he olex2. e ine [25] e inemen package using Gauss-New on minimiza ion. All non-
hyd ogen a oms we e e ined aniso opically, and hyd ogen a oms we e included in he model a
calcula ed posi ions, e ined wi h a igid model wi h hei Uiso alue o 1.2Ueq o hei pa en a oms.
Table 1 epo s he c ys allog aphic da a and expe imen al de ails o da a collec ion and
s uc u e e inemen s. A omic coo dina es and equi alen he mal pa ame e s a e epo ed in Table 2,
selec ed bond dis ances in Table 3. The s uc u al g aphics we e c ea ed using bo h DIAMOND
p og am [26] and Me cu y [27].
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Table 1. Expe imen al da a collec ion de ails om [(C4N2H14)Co(H2PO3)4·2H2O].
Chemical Fo mula/M (g/mol)
[(C4N2H14)Co(H2PO3)4·2H2O]/509.08
F(000)
263.9
Symme y, S.G.
T iclinic (P-1, #2)
Cell pa ame e s (Å , °)/V (Å 3)/Z
a = 5.4814 (3), b = 7.5515 (4), c = 10.8548 (6), α = 88.001 (4), β =
88.707 (5)°, γ = 85.126 (5)°/447.33 (4)/1
λ (Mo Kα adia ion) (Å)
0.71073
T(K)/µ(mm−1)
298/1.39
C ys al sizes (mm)
0.25 × 0.25 × 0.3
Measu ed e lec ions/independen e lec ions
( e lec ions wi h I ≥ 2u(I))/pa ame e s
9480/2005 (1878)/137
θmin − θmax (°)/Rin
1.9–27.8/0.024
Recip ocal space
h: −6–7, k: −9–9, l: −13–14
R[F2 > 2σ(F2)]/wR(F2)/S
0.026/0.072/1.03
Table 2. F ac ional a omic coo dina es and displacemen pa ame e s (Å 2) o he a oms in
[(C4N2H14)Co(H2PO3)4·2H2O] (“*” iso opic pa ame e s o H a oms).
x
y
z
Uiso*/Ueq
Co1
0.5
0
0.5
0.01218 (11)
P5
−0.02030 (8)
0.22049 (6)
0.42698 (4)
0.01422 (12)
H5
−0.007 (4)
0.111 (3)
0.344 (2)
0.021 (5) *
P7
0.52560 (9)
−0.06370 (6)
0.80899 (4)
0.01853 (13)
H7
0.634 (5)
−0.223 (3)
0.790 (2)
0.033 (6) *
O2
0.2188 (2)
−0.17568
(17)
0.48203 (12)
0.0186 (3)
O3
0.4308 (2)
0.01773 (18)
0.68967 (11)
0.0221 (3)
O4
0.2349 (2)
0.22465 (16)
0.47498 (12)
0.0183 (3)
O6
−0.0899 (3)
0.4083 (2)
0.36416 (14)
0.0276 (3)
H6
−0.234 (6)
0.439 (4)
0.365 (3)
0.051 (9) *
O8
0.6876 (3)
0.0461 (2)
0.87800 (13)
0.0335 (4)
O9
0.3019 (3)
−0.1124 (2)
0.89129 (13)
0.0346 (4)
H9
0.324 (2)
−0.087 (4)
0.9627 (5)
0.0519 (6) *
O13
−0.5521 (3)
0.5209 (2)
0.35642 (15)
0.0261 (3)
H13a
−0.574 (6)
0.602 (4)
0.387 (3)
0.044 (9) *
H13b
−0.607 (5)
0.442 (4)
0.388 (2)
0.030 (7) *
N12
0.0271 (3)
0.2595 (2)
0.77025 (14)
0.0220 (3)
H12a
−0.027 (2)
0.3488 (2)
0.7196 (6)
0.0264 (4) *
H12b
0.1433 (7)
0.1909 (15)
0.7321 (7)
0.0264 (4) *
H12c
−0.0966 (17)
0.1953 (15)
0.79227 (19)
0.0264 (4) *
C10
−0.0486 (4)
0.4687 (3)
0.94033 (18)
0.0263 (4)
H10a
−0.2031 (4)
0.4179 (3)
0.95693 (18)
0.0316 (5) *
H10b
−0.0785 (4)
0.5696 (3)
0.88336 (18)
0.0316 (5) *
C11
0.1294 (4)
0.3320 (3)
0.88205 (18)
0.0264 (4)
H11a
0.1693 (4)
0.2355 (3)
0.94144 (18)
0.0316 (5) *
H11b
0.2794 (4)
0.3857 (3)
0.85960 (18)
0.0316 (5) *
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Table 3. Basic geome ical da a om [(C4N2H14)Co(H2PO3)4·2H2O].
Co1—O2
2.1336 (12)
P5—O6
1.5732 (14)
Co1—O2i
2.1336 (12)
P7—O3
1.4987 (13)
Co1—O3
2.0919 (12)
P7—O8
1.4955 (15)
Co1—O3i
2.0919 (12)
P7—O9
1.5625 (15)
Co1—O4i
2.1519 (12)
N12—C11
1.489 (2)
Co1—O4
2.1519 (12)
C10—C10iii
1.517 (4)
P5—O2ii
1.5050 (13)
C10—C11
1.505 (3)
P5—O4
1.5067 (13)
O2i—Co1—O2
180
O4—Co1—O3
87.41 (5)
O3i—Co1—O2
88.26 (5)
O4i—Co1—O4
180
O3—Co1—O2
91.74 (5)
O4—P5—O2ii
117.53 (7)
O3—Co1—O2i
88.26 (5)
O6—P5—O2ii
109.58 (8)
O3i—Co1—
O2i
91.74 (5)
O6—P5—O4
106.61 (8)
O3i—Co1—O3
180
O8—P7—O3
115.59 (9)
O4—Co1—O2i
90.01 (5)
O9—P7—O3
108.23 (8)
O4—Co1—O2
89.99 (5)
O9—P7—O8
110.69 (8)
O4i—Co1—
O2i
89.99 (5)
P5ii—O2—Co1
129.16 (7)
O4i—Co1—O2
90.01 (5)
P7—O3—Co1
139.61 (8)
O4i—Co1—
O3i
87.41 (5)
P5—O4—Co1
126.28 (7)
O4i—Co1—O3
92.59 (5)
C10—C11—N12
111.66 (16)
O4—Co1—O3i
92.59 (5)
Symme y codes: (i) −x + 1, −y, −z + 1; (ii) −x, −y, −z + 1; (iii) −x, −y + 1, −z + 2.
Supplemen a y ables o c ys al s uc u es and e inemen s, no ably he ull lis o bond leng hs
and angles, and aniso opic he mal pa ame e s we e deposi ed wi h he Ino ganic C ys al S uc u e
Da abase, FIZ, He mann on Helmhol z Pla z 1, 76344 Eggens einLeopoldsha en, Ge many; ax: (+49)
7247 808 132; Email: c ysda a@ iz-ka ls uhe.de. Deposi ion numbe is CCDC 1882579.
2.4. Biological Ac i i ies
2.4.1. Nema icidal Ac i i y
The model nema ode S eine nema el iae was pu chased om Sau e und S eppe GmbH
(Amme buch, Ge many) in he o m o powde and s o ed a 4 °C in he da k. F esh samples we e
u ilized p io o each expe imen . A homogeneous mix u e was p epa ed by dissol ing 200 mg o
nema ode powde in 50 mL dis illed wa e . La e on, he nema ode suspension was placed o 15 min
a oom empe a u e wi h shaking and in mode a e ligh . Viabili y was examined unde a ligh
mic oscope a ou - old magni ica ion (TR 200, VWR In e na ional, Leu en, Belgium). The iabili y
o nema odes abo e 80% in each sample was conside ed a p e equisi e o each expe imen . Ten
mic oli e s o nema ode suspension we e added o each well o a 96-well pla e. The hyb id cobal
phosphi e [(C4N2H14)Co(H2PO3)4·2H2O] was hen added in o he wells o achie e inal concen a ions
o 250, 500, and 1000 µM. A e wa d, he inal olume in each well was adjus ed o 100 µL by adding
Phospha e Bu e ed Saline (PBS pH = 7.4). PBS and e hanol (10 µL pe well) we e employed as
nega i e and posi i e con ols, espec i ely, and s e ile dis illed wa e was he sol en con ol. Each
expe imen was pe o med independen ly on h ee di e en occasions and in iplica e (n = 9). Li ing
and dead nema odes we e coun ed unde he mic oscope p io o ea men , and he iabili y ac ion
(V0) was calcula ed (usually >0.9). Then, 50 µL o lukewa m wa e (40 °C) was added o each well o
s imula e he nema odes p io o coun ing. A e 24 h, he V24 ac ion was calcula ed, by once mo e
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coun ing he li ing and dead nema odes, and exp essed as a pe cen age o ini ial iabili y V0
acco ding o he equa ion:
Viabili y (%) = [V24/V0] × 100
Resul s a e ep esen ed as mean ± SD, and G aphPad P ism (Ve sion 5.03, G aphPad So wa e,
La Jolla, CA, USA) was used o calcula e he s a is ical signi icances by one-way ANOVA. p < 0.05
was conside ed o be s a is ically signi ican .
2.4.2. The An imic obial Ac i i y
This sec ion may be di ided by subheadings. I should p o ide a concise and p ecise desc ip ion
o he expe imen al esul s, hei in e p e a ion, as well as he expe imen al conclusions, ha can be
d awn. The ac i i y o [(C4N2H14)Co(H2PO3)4·2H2O] compound agains Esche ichia coli, S aphylococcus
epide midis, Candida albicans, and Saccha omyces ce e isiae was in es iga ed in ou ine mic obial g ow h
assays based on op ical densi y and eco ded in he o m o g ow h cu es. F esh cul u es o S.
epide midis, E. coli, C. albicans, and S. ce e isiae we e p epa ed on bac e ial yp ic soy b o h, Lu ia-
Be ani b o h (LB), Sabou aud Dex ose Aga (SDA), and Yeas Pep one Dex ose (YPD) aga media,
espec i ely. A e 18–24 h o incuba ion, he mic obial colonies om hese Aga pla es we e hen
ans e ed in o 10 mL solu ion o 0.9% w/ NaCl (saline), and he u bidi y o he suspension was
adjus ed o 0.5 o McFa land s anda d. These mic obial suspensions we e hen exposed o he
samples as desc ibed below. Bac e ial and yeas cul u e wi h g ow h medium we e employed as
nega i e con ol, s e ile dis illed wa e was u ilized as sol en con ol, while he posi i e con ol
consis ed o a mix u e o 10,000 uni s/mL o penicillin, 10,000 µg/mL o s ep omycin, and 25 µg/mL
o ampho e icin B. The sample was e alua ed a a ious dilu ions (o 250, 500, and 1000 µM), and he
pla es we e incuba ed a 37 °C o 24 h. Mic obial g ow h was moni o ed by eco ding he op ical
densi y o he samples a 0 h and 24 h, using a Mic o Pla e Reade E800 a 593 nm. These abso bance
alues we e con e ed in o pe cen ages and compa ed o he nega i e con ol whose abso bance
alues we e no malized o 100% and se ed as e e ences a each ime in e al. All expe imen s we e
ca ied ou in iplica e a h ee di e en occasions (n = 9). Resul s a e ep esen ed as mean ± SD, and
s a is ical signi icances we e calcula ed by one-way ANOVA using G aphPad P ism (Ve sion 5.03,
G aphPad So wa e, La Jolla, CA, USA) wi h p < 0.05 conside ed o be o s a is ical signi icance.
3. Resul s and Discussion
3.1. S uc u al Desc ip ion
As shown in Figu e 1, he e is one c ys allog aphically dis inc si e o Co a om in he asymme ic
uni o [(C4N2H14)Co(H2PO3)4·2H2O] which con ains 13 non-hyd ogen a oms. The six coo dina ed
cobal exhibi s oc ahed al geome y by oxygen dono s om he adjacen phosphi e g oups. The Co–
O bond leng hs ange om 2.0920 (1) Å o 2.1336 (1) Å wi h an a e age Co–O dis ance o 2.1258 Å , a
compa able alue o ha o 2.113 Å epo ed in [(C4N8H12)Co(HPO3)2(C2O4)3] [28] and o ha o 2.101
Å o NaCo(H2PO3)3·H 2O [29]. All H2PO3 uni s adop pseudo py amidal coo dina ion geome y. P(5)
sha es wo oxygen wi h adjacen Co a oms, while P(7) is connec ed by one P–O–Co bond and
possesses a sho e minal P–O bond (1.4945 (1) Å ). The P–O bond dis ances a e in he ange
1.5049(1)–1.5372 (1) Å o P(5) a om [A . 1.5282 Å ] and 1.495 (1)–1.506 (1) Å o P(7) [A . 1.499 Å ].
P(5) and P(7) a oms ha e a e minal phosphi e P–H bond 1.241 (1) and 1.3127 (1) Å , espec i ely.
These alues a e o he usual magni ude as he ones epo ed in (C2NH8)2[Co3(HPO3)4],
(C4N2H12[Co(HPO3)2] [30], and (C6H16N2)[Co(HPO3)F] [31]. The s ic al e na ion o CoO6 oc ahed a
and H2PO3 pseudo py amids ia oxygen e ices esul s in an anionic ne wo k wi h a Co/P a io o
1/2. The polyhed al uni s a e joined h ough co ne s sha ing ou -membe ed ings, which a e he eby
connec ed h ough hei edges o ming an in ini e one-dimensional chain ising along [100] (Figu e 2).
The indi idual chain uni s a e u he linked oge he h ough hyd ogen bond in e ac ions (Figu e 3,
Table 4). The 1,4-diaminobu ane empla es, which eside be ween he pa allel chains, a e

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dip o ona ed. They a e u he ensu ing, oge he wi h he ee wa e molecules, he s abili y o he
h ee-dimensional ne wo k.
Figu e 1. The asymme ic uni o [(C4N2H14)Co(H2PO3)4·2H2O]. The mal ellipsoids a e shown a 50%
p obabili y.
Figu e 2. A agmen o he s uc u e o [(C4N2H14)Co(H2PO3)4·2H2O] along [010], showing he in ini e
ou -membe ed ing chain p opaga ing along [100].
Figu e 3. The c ys al s uc u e o [(C4N2H14)Co(H2PO3)4·2H2O] in a p ojec ion along c-axis
emphasizing he hyd ogen bonds (dashed lines).
Table 4. H-bonds dis ances in he amewo k o [(C4N2H14)Co(H2PO3)4·2H2O].
D-H⋯A
D-H/Å
H⋯A/Å
D⋯A/Å
Angle DHA/°
O6-H6⋯O13
0.80 (3)
1.80 (3)
2.605 (2)
175 (3)
O9-H9⋯O8
0.819 (10)
1.766 (8)
2.574 (2)
168.5 (16)
N12-H12A⋯O6
0.890 (5)
2.158 (5)
2.900 (2)
140.3 (9)
N12-H12B⋯O3
0.890 (8)
2.016 (8)
2.887 (2)
165.5 (7)
N12-H12C⋯O8
0.890 (10)
1.907 (9)
2.776 (2)
164.8 (5)
O13-H13A⋯O2
0.71 (3)
2.22 (3)
2.888 (2)
159 (3)
O13-H13B⋯O4
0.76 (3)
2.11 (3)
2.863 (2)
179 (4)
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3.2. In a ed Spec oscopy
The in a ed spec um o [(C4N2H14)Co(H2PO3)4·2H2O] (Figu e 4) exhibi s bands co esponding
o he ib a ion modes o he o ganic empla e and phosphi e g oups. The s e ching ib a ion o NH2
in dabn ca ion is obse ed in he high equencies 3090–3200 cm−1, while i s bending appea s a 1600
cm−1 [32]. The alues a a ound 2850 and 1300 cm−1 a e boil down o he s e ching ib a ion o CH2
and C–N, espec i ely. The band appea ing a 2450 cm−1 co esponds o he s e ching ib a ion o P–
H bond which is he cha ac e is ic bond o phosphi e g oups, whe eas he bands om 990 o 1030
cm−1 a e assigned o he bending mode o P–H. The ib a ion modes cen e ed a 570, 1050, and 1160
cm−1 a e asc ibed o he s e ching ib a ion o PO3 g oup, while he one loca ed a 910 cm−1 p esen s
he s e ching ib a ion o P–OH [20]. The se o bands ela ed o he s e ching ib a ion and
de o ma ion o he OH g oup belonging o wa e molecules is obse ed a a ound 3000 and 1640 cm−1
[33,34].
Figu e 4. The in a ed spec um o [(C4N2H14)Co(H2PO3)4·2H2O].
3.3. The mal Beha io
TGA expe imen was pe o med unde an ai a mosphe e. The expe imen al da a, gi en om
TG analysis (Figu e 5), show h ee sepa a ed s eps o weigh loss in a o al o 45% o
[(C4N2H14)Co(H2PO3)4·2H2O]. The i s mass loss o 10% in he ange o 180–220 °C is accompanied by
an endo he mic signal in he di e en ial he mal analysis (DTA) ace a 180 °C. The peak
coincidences wi h he depa u e o 1.5 wa e molecules (calcula ed mass 9.8%). The second s age wi h
a heo e ical weigh loss o 8% s a ing a abou 320 °C and ending a 420 °C can be ela ed o he
decomposi ion o 1,4-diaminobu ane (calcula ed weigh loss 8%). This phenomenon is coupled wi h
an exo he mic hea low no iced a 340 °C. The o al decomposi ion o he o ganic moie y and he
emaining wa e molecules is shown be ween 540–660 °C (obse ed weigh loss 27%), wi h a small
exo he mic cu e a 640 °C (calcula ed weigh loss 27.8%).
Sci 2019, 1, 13 8 o 12
Figu e 5. The mog a ime ic (TG) and di e en ial he mal analysis (TDA) cu es o
[(C4N2H14)Co(H2PO3)4·2H2O].
3.4. Biological Ac i i ies
The hyb id cobal phosphi e compound was es ed o hei an imic obial ac i i y agains wo
bac e ial (Esche ichia coli and S aphylococcus epide midis) and wo ungal (Saccha omyces ce e isiae and
Candida albicans) s ains. The mix u e o 10,000 uni s/mL o penicillin, 10,000 µg/mL o s ep omycin,
and 25 µg/mL o Ampho e icin B was used as con ol d ugs. The pe cen age inhibi ion and minimum
inhibi o y concen a ion (MIC) alues o he compound based on he g ow h o mic oo ganisms a e
shown in Figu e 6a. The highes inhibi ion ac i i y o he compound was obse ed agains C. albicans
ungi wi h a MIC alue o 500 µg·mL−1. The compound showed a lowe ac i i y agains E. coli (1000
µg·mL−1) han posi i e con ol, while no signi ican ac i i y was obse ed agains S. ce e isiae and S.
epide midis s ains.
The nema icidal ac i i y o (C4N2H14)Co(H2PO3)4 was in es iga ed agains S. el iae nema ode.
E hanol was used as a posi i e con ol. No mo ali y o nema odes was obse ed; such a esul
indica es ha he hyb id compound was inac i e agains S. el iae (Figu e 6b).
Sci 2019, 1, 13 9 o 12
E. coli
- e con ol
+ e con ol
sol en con ol
M

250 M

500 M

1000
M

250 M

500 M

1000
0
50
100
**
***
***
Con ols Compound
*
*p < 0.05, ** p < 0.01, *** p < 0.001
G ow h(%)
C. albicans
- e con ol
+ e con ol
sol en con ol
M

250 M

500 M

1000
M

250 M

500 M

1000
0
20
40
60
80
100
***
**
******
Con ols compound
*p < 0.05, ** p < 0.01, *** p < 0.001
G ow h (%)
(a)
S. el iae
- e con ol
+ e con ol
sol en con ol
M

250
M

500
M

1000
0
50
100
***
con ols compound
*p < 0.05, ** p < 0.01, *** p < 0.001
Viabili y (%)
(b)
Figu e 6. An ibac e ial ac i i y o [(C4N2H14)Co(H2PO3)4 agains bac e ial and ungal s ains (a) and S.
el iae nema ode (b).