Synthesis, characterization and biological evaluation of two silver(I) trans-cinnamate complexes as urease inhibitors

Article abstract of DOI:10.1002/zaac.201300270

Two new silver(I) trans-cinnamates, namely [Ag(2-cca)(H₂O)] ₂ (1) and [Ag(4-cca)]_n (2) (2-ccaH = 2-chlorocinnamic acid and 4-ccaH = 4-chlorocinnamic acid), were synthesized and structurally characterized. Single crystal X-ray studies reveal that each silver(I) atom in 1 is two-coordinate by a 2-chlorocinnamate ligand and one water molecule to afford a discrete centrosymmetric dimer with the ligand-unsupported Ag···Ag interactions (3.218(4) A), while a pair of symmetry-related silver(I) atoms in 2 are clamped by two μ₂- η¹:η¹ 4-chlorocinnamate ligands to yield a binuclear silver(I) moiety incorporating a ligand-supported Ag·· ·Ag interaction (2.819(5) A). Both complexes 1 and 2 show potent urease inhibitory activities with the respective IC₅₀ values of 0.66 and 1.10 μM. Copyright

Full text of DOI:10.1002/zaac.201300270

ARTICLE
DOI: 10.1002/zaac.201300270
Synthesis, Characterization and Biological Evaluation of Two Silver(I) trans-
Cinnamate Complexes as Urease Inhibitors
Xia Li,[a][‡] Yan Wang,[a][‡] Yuguang Li,*[a] Yi Gou,[a] and Qiang Wang*[a]
Keywords: Silver; Solid-state structures; Substituent effects; trans-Cinnamate ligands; Urease inhibitors
Abstract.
Two
new
silver(I)
trans-cinnamates,
namely
mer with the ligand-unsupported Ag···Ag interactions (3.218(4) Å),
while a pair of symmetry-related silver(I) atoms in 2 are clamped by
two μ2-η1:η1 4-chlorocinnamate ligands to yield a binuclear silver(I)
[Ag(2-cca)(H2O)]2 (1) and [Ag(4-cca)]n (2) (2-ccaH = 2-chlorocin-
namic acid and 4-ccaH = 4-chlorocinnamic acid), were synthesized
and structurally characterized. Single crystal X-ray studies reveal that moiety incorporating
a
ligand-supported Ag···Ag interaction
each silver(I) atom in 1 is two-coordinate by a 2-chlorocinnamate li- (2.819(5) Å). Both complexes 1 and 2 show potent urease inhibitory
gand and one water molecule to afford a discrete centrosymmetric di- activities with the respective IC50 values of 0.66 and 1.10 μM.
peutic applications of a series of silver(I) complexes with vari-
Introduction
ous carboxylate groups.[16–19] Currently our group is interested
Silver(I) complexes derived from diverse carboxylic acids
in the inhibitory activity of such silver(I) complexes as a ure-
have been of great interest in recent years because of their
ase inhibitor. In this paper, we report the synthesis, structures,
fascinating architectures in the areas of coordination polymers,
supramolecular chemistry and crystal engineering.[1–5] They
and urease inhibitory activities of two new silver(I) trans-cin-
namates, [Ag(2-cca)(H2O)]2 (1) and [Ag(4-cca)]n (2), where 2-
additionally exhibit antimicrobial and antifungal properties
ccaH is 2-chlorocinnamic acid and 4-ccaH is 4-chlorocinnamic
that can be utilized in the fields of the biological and pharma-
acid.
cological chemistry.[6–10] Among the potential applications of
silver(I) complexes as functional materials, the Ag-based anti-
septic materials may be linked to far less propensity to induce
microbial resistance than antibiotics.[11] In addition, silver(I)
Results and Discussion
IR and H NMR Spectroscopy
1
ions have remarkably low human toxicity compared with other
The complexes obtained in this work were characterized in
heavy metal ions.[12] For this reason, the molecular design of detail by IR spectroscopy. The proposed assignments in the
silver(I) complexes with antimicrobial and antifungal activities infrared spectra of silver(I) trans-cinnamates (1) and (2) are
is an intriguing aspect of bioinorganic chemistry of metal- based on previously reported results.[20–22] The IR spectrum of
based drugs.[13]
complex 1 shows the stretching vibrations of the ν(O–H) band
at ca. 3340 cm–1. The ν(C–H) stretching vibrations of 1 and 2
are centered at 3057 and 3030 cm–1, respectively. Both com-
plexes 1 and 2 display characteristic bands of deprotonated
carboxylate groups. The carboxylate νas(COO–) and νs(COO–)
stretching vibrations in the IR spectrum of 1 are present at
1557s and 1394s cm–1, respectively. Owing to the presence of
the pseudo-bridging carboxylate via hydrogen bonds, its
Δ(COO–) value of 163 cm–1 is significantly lower than that
expected for monodentate carboxylate ligands (Ͼ 200 cm–1).
In contrast, the carboxylate νas(COO–) and νs(COO–) vi-
brations in 2 occur at 1553s and 1383s cm–1, respectively, giv-
ing a Δ(COO–) value of 170 cm–1. This value is indicative of
bridging modes of coordination in 2, when compared with that
of 105–142 cm–1 found for the bridging carboxylates.[9] The
strong absorption bands at 1044 and 1090 cm–1 in the IR spec-
tra of 1 and 2 are due to the ν(C–Cl) stretching vibration,
respectively. Complexes 1 and 2 show additional weak bands
in the region 412–493 cm–1, which can be attributed to the
Silver(I) carboxylate complexes have been reported to show
a variety of noteworthy antimicrobial activities, although mode
of action and mechanism of their antimicrobial activities are
not clarified. It was suggested that one of the key factors de-
termining antibacterial effects of silver(I) complexes is the na-
ture of the coordinate bond between ligand and silver(I) ion
and the bonding properties such as the ease of ligand replace-
ment and degree of polymerization of the compounds.[14,15]
Our previous work has focused on the synthesis and thera-
* Prof. Y. Li
Fax: +86-27-8761-1776
E-Mail: liyg2010@wtu.edu.cn
* Prof. Q. Wang
E-Mail: wangqche@hotmail.com
[a] School of Chemistry and Chemical Engineering,
Wuhan Textile University
Wuhan 430073, P. R. China
[‡] These authors contributed equally to this work.
Supporting information for this article is available on the WWW
under http://dx.doi.org/10.1002/zaac.201300270 or from the au-
thor.
1
ν(Ag–O) vibration. The H NMR spectroscopic data of 1 and
Z. Anorg. Allg. Chem. 2014, 640, (2), 423–428
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
423

X. Li, Y. Wang, Y. Li, Y. Gou, Q. Wang
ARTICLE
2 are in agreement with their solid-state structures (Figs. S1, one oxygen atom (O3) of the coordinated water molecule. The
S2 and S3, Supporting Information). The 1H NMR spectra O1–Ag1–O3 angle is 172.55(15)°, deviating from the ideal
show characteristic doublet signals at δ = 6.56 and 7.62 ppm 180°. This may result from the existence of weak Ag1···O2
in 1 and 6.54 and 7.32 ppm in 2 for the respective Ph–CH=CH (2.690(4) Å) and Ag1···Ag1i (3.2184(11) Å) interactions. The
unit with a coupling constant of J = 16.0 Hz, corresponding to Ag···Ag distance is shorter than the sum of their van der Waals
1
their trans configurations. Besides, the H NMR spectrum of radii (3.44 Å), which is similar to those observed in analogous
1 displays one broader singlet at δ = 3.32 ppm for the coordi- silver(I) complexes.[23,24] This indicates the existence of sig-
nated water molecules.
nificant argentophilic interactions. Interestingly the discrete di-
meric moieties of complex 1 are further linked by two intermo-
lecular O3–H···O2# hydrogen bonds between a coordinated lat-
tice water molecule and an adjacent carboxylate oxygen atom
(O2#) as depicted in Figure 2 and Figure 3, where # refers to
the different 2-chlorocinnamate ligand. One is the O3–
H3X···O2i hydrogen bond with a O3···O2i distance of
3.126(6) Å and the O3–H3X···O2i angle of 127.8(6)°, giving a
one-dimensional (1D) zigzag chain (Symmetry code: (i) 2–x,
y, 3/2–z; Figure 2), while the other is the O3–H3Y···O2ii hydro-
gen bonds with a O3···O2ii distance of 2.930(6) Å and a O3–
H3Y···O2ii angle of 170.4(6)°, offering a two-dimensional
(2D) 4-connected sheet structure in the bc plane (Symmetric
code: (ii) 2–x, –1+y, 3/2–z; Figure 3). Using the dimeric silver
moieties as nodes, it shows a classic 4-connected sql topologi-
cal net with the Schläfli symbol of (44.62) (Figure 4).
Crystal Structure Description
[Ag(2-cca)(H2O)]2 (1)
The molecular structure of silver(I) trans-2-chlorocinnamate
(1) was determined by single-crystal X-ray analysis as depicted
in Figure 1. It crystallizes in the monoclinic system, space
group C2/c (No. 15). Complex 1 contains a discrete non-
bridged centrosymmetric dimer, [Ag(2-cca)(H2O)]2, con-
structed by the ligand-unsupported Ag···Ag interactions
(Ag1···Ag1i = 3.2184(11) Å; Symmetry code: (i) 2–x, –y, 2–z).
Each silver atom is two coordinated by one oxygen atom (O1)
of the carboxylate group from 2-chlorocinnamate ligand and
Figure 1. Ball-and-stick representation of the molecular structure of 1.
Selected bond lengths /Å and angles /°: Ag1–O1 2.164(4); Ag1–O2
2.690(4); Ag1–O3 2.120(4); Ag1–Ag1i 3.2184(11); O1–Ag1–O3
172.55(15); O1–Ag1–Ag1i 85.72(10); O3–Ag1–Ag1i 88.98(12). Sym-
metry codes: (i) 2–x, –y, 2–z; (ii) x, 1–y, 1/2+z; (iii) x, –y, 1/2+z; (iv)
x, –1–y, 1/2+z; (v) 2–x, –1+y, 3/2–z; (vi) 2–x, y, 3/2–z; (vii) 2–x, 1+y,
3/2–z.
Figure 3. View of the two-dimensional (2D) layer of 1 constructed
by the O3i–H3Yi···O2 and O3–H3Y···O2ii hydrogen bonds. Symmetry
codes: (i) 2–x, 1+y, 3/2–z; (ii) 2–x, –1+y, 3/2–z.
Figure 2. One-dimensional (1D) zigzag chain of 1 constructed by the
O3–H3X···O2i and O3i–H3Xi···O2 hydrogen bonds. Symmetry code:
(i) 2–x, y, 3/2–z.
Figure 4. The twofold interpenetrated 4-connected net with sql top-
ology of 1.
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Silver(I) trans-Cinnamate Complexes as Urease Inhibitors
[Ag(4-cca)]n (2)
The molecular structure of silver(I) trans-4-chlorocinnamate
(2) is depicted in Figure 5. Single crystal X-ray diffraction re-
veals that the complex 2 crystallizes in the monoclinic system,
space group P21/c (No. 14). Complex 2 consists of the centro-
symmetric dimeric silver(I) moieties [Ag(4-cca)]2. Herein, two
silver atoms are clamped in a bridging mode by two 4-chloro-
cinnamate ligands related by the inversion center to yield a
[Ag(4-cca)]2 dimer. The Ag1···Ag1i distance (2.8187(5) Å;
Symmetry code: (i) 1–x, –y, –z) in the dimer is significantly
shorter than the sum of their van der Waals radii (3.44 Å),
reflecting a strong ligand supported argentophilic interaction.
The typical Ag···Ag distances in the range of 2.80–2.95 Å are
Figure 5. Ball-and-stick representation of molecular structure of 2. Se-
similar to those of analogous dinuclear silver(I) struc- lected bond lengths /Å and angles /°: Ag1–O1 2.216(2); Ag1iv–O1
2.622(2); Ag1i–O2 2.203(2); Ag1v–O2 2.507(2); Ag1–Ag1i 2.8187(5);
Ag1–O1–Ag1iv 97.37(9); Ag1i–O2–Ag1v 101.20(9); O1–Ag1–O2i
164.42(9); O1–Ag1–O2iii 81.31(8); O1–Ag1–O1ii 103.92(9);
O2i–Ag1–O2iii 114.23(9). Symmetry codes: (i) 1–x, –y, –z; (ii) x, 1/2–
y, –1/2+z; (iii) 1–x, 1/2+y, 1/2–z; (iv) x, 1/2–y, 1/2+z; (v) 1–x, –1/2+y,
1/2–z; (vi) x, –1/2–y, –1/2+z; (vii) 1–x, –1/2+y, –1/2–z.
tures.[25–28] These dimeric moieties are further linked by the
weak Ag···O interactions into a 2D sheet structure (Figure 6).
Thus, each silver(I) atom in the crystal structure of 2 is four
coordinated by four different 4-chlorocinnamate ligands be-
having as a μ4-η2:η2 bridge to yield a distorted tetrahedral
coordination environment (τ4 = 0.58).[29] The Ag–O distances
in the range from 2.203(2) Å to 2.623(2) Å are shorter than
the sum of the van der Waals radii (3.24 Å) of the silver(I)
cation and oxygen atom, suggesting the existence of significant
Ag···O interactions. As depicted in Figure 5, the plane defined
by Ag1/O1/O2/Ag1i/O1i/O2i in the dimeric Ag2O4 core is al-
most coplanar (mean deviation from plane: 0.066 Å; Sym-
metry code: (i) 1–x, –y, –z), which makes the dihedral angles
ca. 19.8° and 62.5° with the adjacent rectangle planes Ag1/O1/
Ag1iv/O2iii (mean deviation from plane: 0.168 Å; Symmetric
codes: (iii) 1–x, 1/2+y, 1/2–z; (iv) x, 1/2–y, 1/2+ z) and Ag1/
O2i/Ag1ii/O1ii (mean deviation from plane: 0.168 Å; Symmet-
ric code: (ii) x, 1/2–y, –1/2+z), respectively. Taking Ag···Ag
interactions into consideration, the whole 2D structure exhibits
an unprecedented binodal (4,5)-connected topology with the
vertex symbol (3.43.52)(32.44.52.62) (Figure 7). However, com-
plex 2 presents the same topology structure as complex 1 if
the Ag···Ag interactions are not considered.
Figure 6. View of the two-dimensional (2D) layer of 2. Symmetry
codes: (i) 1–x, –y, –z; (ii) x, 1/2–y, –1/2+z; (iii) 1–x, 1/2+y, 1/2–z; (iv)
x, 1/2–y, 1/2+z; (v) 1–x, –1/2+y, 1/2–z; (vi) x, –1/2–y, –1/2+z.
Inhibitory Bioactivity Against Urease
In this work, two new silver(I) trans-cinnamate complexes
were screened for their activity to inhibit jack bean urease.
Compared with acetohydroxamic acid (AHA) co-assayed as a
standard urease inhibitor agent (IC50 = 63.05 μM), silver(I)
trans-cinnamates 1 and 2 displayed good inhibitory activity
with the respective IC50 values of 0.66 and 1.10 μM. The com-
plex 1 herein presents slightly higher inhibitory activity against
jack bean urease than 2, probably as a result of the electron
withdrawing difference of their chlorine-substituted cinnamate
ligands. In this paper the substituted trans-cinnamic acids, 2-
ccaH and 4-ccaH, were found to be inactive against jack bean
urease under identical experimental conditions (IC50 Ͼ 100
μM). The free Ag+ ion showed a strong urease inhibitory ac-
tivity with the IC50 value of 0.85 μM. Similar to the inhibition
by other heavy metal ions,[30–32] the silver(I) ion shows urease
inhibitory activity probably because of its interactions with the
urease active site.
Figure 7. Schematic representation of the (4,5)-connected 2D net with
(3.43.52)(32.44.52.62) topology of 2.
DFT Calculations
The optimized geometries and NBO charge distributions of
2-chlorocinnamic acid (2-ccaH) and 4-chlorocinnamic acid (4-
Z. Anorg. Allg. Chem. 2014, 423–428
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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425

X. Li, Y. Wang, Y. Li, Y. Gou, Q. Wang
ARTICLE
ccaH) were calculated by density functional theory (DFT) with bridging ligands, respectively. This can be further confirmed
B3LYP/6-31+G* level to predict the chlorine substituent effect by their highest occupied molecular orbital (HOMO) energy
on trans-cinnamic acid.[33,34] All quantum chemical calcula- of –0.2557 a.u. for 2-ccaH and –0.2516 a.u. for 4-ccaH. It
tions have been carried out using the GAUSSIAN-03 package. shows that the coordination abilities of the carboxylate oxygen
The computed results reveal that the negative NBO charges of atoms may be enhanced to give the different coordination
the free ligands 2-ccaH and 4-ccaH mainly distribute on the modes.
oxygen atoms (Scheme 1 and Table 1). Compared with 4-
ccaH, 2-ccaH shows that the NBO charge of one oxygen atom
Conclusions
from a carbonyl group of the carboxyl group increases slightly,
while that of the other oxygen atom from a hydroxyl group of
the carboxyl group decreases slightly. These values indicate
that carboxyl groups of the two ligands can display the dif-
ferent coordination modes under suitable reaction conditions.
In this work, 2-ccaH and 4-ccaH act as μ-η2 and μ4-η2:η2
This paper reports the synthesis, crystal structures and ure-
ase inhibition properties of two silver(I) trans-cinnamate com-
plexes. Complex 1 contains a discrete nonbridged dimeric sil-
ver(I) unit [Ag(2-cca)(H2O)]2, while complex 2 presents a li-
gand-bridged dimeric silver(I) moiety [Ag(4-cca)]2. The ob-
tained silver(I) complexes 1 and 2 are potent urease inhibitory
activities. Detailed investigations are continuing to study the
mechanisms of urease inhibitory activity reported here.
Experimental Section
Materials and Methods
Urease (from jack beans, type III, activity 22 units/mg solid), N-[2-
hydroxy-ethyl] piperazine-NЈ-[2-ethanesulfonic acid] (HEPES) buffer
and urea (Molecular Biology Reagent) were from Sigma–Aldrich. All
other chemicals and solvents were purchased from Alfa Aesar and used
without further purification. Distilled water was used for all pro-
1
cedures. H NMR spectra were recorded on a Bruker DRX-400 spec-
trometer. Chemical shifts were reported in ppm from tetramethylsilane
as an internal standard (1H, 0.00 ppm). Elemental analyses (C, N, and
H) were performed using an elementar vario EL III elemental analyzer.
Infrared spectra were recorded using KBr pellets on a Nexus 870 FT-
IR spectrophotometer in the 4000–400 cm–1 range. The enzyme inhibi-
tory activity data were obtained with a Bio-Tek Synergy™ HT En-
zyme-labeled meter.
Scheme 1. The optimized geometries of the free ligands 2-ccaH and
4-ccaH.
Synthesis of [Ag(2-cca)(H2O)]2 (1)
Table 1. NBO charge distributions of the free ligands 2-ccaH and 4-
ccaH.
Complex 1 was prepared by reaction of Ag2O (0.116 g, 0.5 mmol)
with trans-2-chlorocinnamic acid (0.183 g, 1.0 mmol) in 28% aqueous
ammonia solutions (50 mL). The resulting mixture was stirred for 30
minutes at room temperature before being filtered. The filtrate was
kept in air for ca. 10 d with ammonia gas escaping, and block crystals
were obtained. Colorless crystals were isolated, washed three times
with distilled water and dried in a vacuum desiccator containing anhy-
2-ccaH
4-ccaH
Atom number
NBO charge
Atom number
NBO charge
O15
O16
C1
C2
C3
C4
C5
C6
C10
C11
C14
Cl19
H7
H8
H9
H12
H13
H17
H18
–0.60355
–0.73110
–0.24779
–0.02166
–0.11237
–0.18515
–0.23965
–0.21185
–0.15095
–0.31858
0.76729
0.01214
0.26154
0.24474
0.25088
–0.31858
0.24668
0.51966
0.25128
O17
O18
C1
C2
C3
C4
C5
C6
C12
C13
C16
Cl11
H7
H8
H9
H10
H14
H15
H19
–0.60331
–0.73514
–0.24805
–0.18770
–0.10101
–0.18590
–0.24488
–0.04513
–0.14563
–0.14563
0.76667
0.01533
0.26201
0.24830
0.24689
0.26212
0.25508
0.24863
0.51950
1
drous CaCl2. Yield: 0.19 g (63%). H NMR (400 MHz, [D6]DMSO):
δ = 3.32 (s, 2 H, H2O), 6.56 (d, J = 16.0 Hz, 1 H, Ph–C=CH), 7.62
(d, J = 16.0 Hz, 1 H, Ph–CH=C), 7.33–7.81 (m, 4 H, Ph). IR (KBr
(cm–1)): 3340, 3057, 1905, 1642, 1557, 1468, 1394, 1283, 1154, 1044,
971, 757, 734, 679, 588, 444, 412. Anal. C9H8ClO3Ag (307.47): C
35.16, H 2.62; found: C 35.00, H 2.83%.
Synthesis of [Ag(4-cca)]n (2)
A similar procedure using Ag2O (0.116 g, 0.5 mmol) and trans-4-chlo-
rocinnamic acid (0.183 g, 1.0 mmol) yielded colorless crystals of 2.
The crystals were isolated, washed three times with distilled water and
dried in a vacuum desiccator containing anhydrous CaCl2. Yield:
0.19 g (66%). 1H NMR (400 MHz, [D6]DMSO): δ = 6.54 (d, J =
426
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Silver(I) trans-Cinnamate Complexes as Urease Inhibitors
16.0 Hz, 1 H, Ph–C=CH), 7.32 (d, J = 16.0 Hz, 1 H, Ph–CH=C), 7.42
(d, J = 8.4 Hz, 2 H, Ph), 7.62 (d, J = 8.4 Hz, 2 H, Ph). IR (KBr
(cm–1)): 3030, 1906, 1637, 1553, 1488, 1383, 1247, 1090, 973, 824,
729, 663, 493, 454. Anal. C9H6ClO2Ag (289.46): C 37.34, H 2.09;
found: C 37.22, H 2.35%.
Acknowledgments
This work was financially supported by the National Natural Science
Foundation of China (grants 21101122 and 21277106) and China Post-
doctoral Science Foundation (grant 20100481108).
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Table 2. Crystal data for silver(I) trans-cinnamates 1 and 2.
Complex
1
2
Empirical formula
Molecular weight
C9H8AgClO3
307.47
C9H6AgClO2
289.46
Crystal system
Space group
monoclinic
C2/c
monoclinic
P21/c
a /Å
b /Å
c /Å
β /°
39.4283(16)
3.9343(3)
13.4102(9)
102.913(2)
291(2)
2027.6(2)
8
2.014
1200
2.227
1996/0/127
1.038
0.0321, 0.0901
16.1751(13)
8.4181(7)
6.5518(5)
91.5990(10)
298(2)
891.77(12)
4
2.156
560
2.516
1745/0/118
1.007
0.0316, 0.0809
T /K
V /Å3
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20.
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Received: June 4, 2013
Published Online: October 22, 2013
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