Skip to main content

Advertisement

Organic and Medicinal Chemistry Letters
Organic and Medicinal Chemistry Letters Cover Image

In vitro anti-leishmanial and anti-fungal effects of new SbIII carboxylates

Organic and Medicinal Chemistry Letters volume 1, Article number: 2 (2011) | Download Citation

Article metrics

  • 7716 Accesses

  • 9 Citations

Abstract

Ring opening of phthalic anhydride has been carried out in acetic acid with glycine, β-alanine, L-phenylalanine, and 4-aminobenzoic acid to yield, respectively, 2-{[(carboxymethyl)amino]carbonyl}benzoic acid (I), 2-{[(2-carboxyethyl)amino]carbonyl}benzoic acid (II), 2-{[(1-carboxy-2-phenylethyl)amino]carbonyl}benzoic acid (III), and 2-[(4-carboxyanilino)carbonyl]benzoic acid (IV). Compounds I-IV have been employed as ligands for Sb(III) center (complexes V-VIII) in aqueous medium. FTIR and 1H NMR spectra proved the deprotonation of carboxylic protons and coordination of imine group and thereby tridentate behaviour of the ligands as chelates. Elemental, MS, and TGA analytic data confirmed the structural hypothesis based on spectroscopic results. All the compounds have been assayed in vitro for anti-leishmanial and anti-fungal activities against five leishmanial strains L. major (JISH118), L. major (MHOM/PK/88/DESTO), L. tropica (K27), L. infantum (LEM3437), L. mex mex (LV4), and L. donovani (H43); and Aspergillus Flavus, Aspergillus Fumigants, Aspergillus Niger, and Fusarium Solani. Compound VII exhibited good anti-leishmanial as well as anti-fungal impacts comparable to reference drugs.

Background

Trivalent antimony reagents are extensively consumed in industrial processes, e.g., in catalysis for the synthesis of polymers akin ethyleneterephthalate, with different brand names like Dacron® and Mylar®. Similarly, antimony alkoxides have also been employed as precursors for the deposition of thin films of Sb2O3 and Sb6O13 [1–4]. The literature also revealed use of trivalent antimony compounds in fluorine chemistry and their suitability as solid electrolytes, piezoelectrics, and ferroelectrics [5, 6]. On the other hand, the use of tri- and pentavalent antimony containing compounds as drugs for the treatment of leishmaniasis span more than 50 years; but little is known about the actual mechanisms of antimony toxicity and drug resistance [7, 8]. Carboxylic group-containing compounds are versatile ligands to act as unidentate, bidentate, or bridging ligands; moreover, these also act as a spacer between Sb and other moieties [9–13]. All these facts prompted us to investigate the chemistry as well and biocidal effects of antimonyIII complexes formed with ligands containing two carboxylic groups.

Experimental

As received grade chemicals used during this study were procured from Sigma; the solvents were dried as reported [14]. C, H, and N analyses were carried out on a Yanaco high-speed CHN analyzer; antipyrene was used as a reference, while antimony was estimated according to the reported procedure [15]; melting points were recorded on Gallenkmp capillary melting point apparatus and are uncorrected. FTIR spectra of all the compounds were taken on Bruker FTIR spectrophotometer TENSOR27 using OPUS software in the range of 5000-400 cm-1 (ZnSe). 1H and 13C NMR spectra in DMSO were recorded on a multinuclear Avance 300 and 75 MHz FT NMR spectrometer operating at room temperature, i.e., 25 C. Thermoanalytical measurements were carried out using a Perkin Elmer Thermogravimetric/differential thermal analyzer (YRIS Diamond TG-DTA High Temp. Vacu.) consuming variable heating rates between 0.5°C/min and 50°C/min. HR FAB-MS spectra were obtained from a double-focusing mass spectrometer Finnigan (MAT 112).

Synthesis of ligands

Phthalic anhydride (5 g, 33.77 mM) was dissolved in acetic acid (100 mL), and a cold solution of amino acid (33.77 mM, i.e. 2.53 g, 3 g, 5.58 g, and 4.63 g of glycine, β-alanine, L-phenylalanine, and 4-aminobenzoic acid, respectively) in acetic acid (75 mL) was added to it. This mixture was stirred at room temperature for 3 hours resulting in white precipitate. The white precipitate was washed several times with cold water and recrystallized from water.

Synthesis of I

Yield: 72%. C10H9NO5: Calcd. (%): C 53.82, H 4.06, and N 6.28; Found (%): C 53.27, H 3.86, N 6.01; FAB-MS (m/z) 224 (M + 1); IR ν 3293 (N-H), 1684 (C-N), 1592 (CO2)as, and 1353 (CO2)s, Δν (CO2): 239 cm-1. 1H NMR (DMSO-d6, 300 MHz) 12.8 (s, COOH), 12.1 (s, COOH), 8.31 (s, NH), 7.02-7.61 (Ar), and 3.62 (s, CH2). 13C NMR (DMSO-d6, 75 MHz) 174.7 (COOH), 170.2 (CONH), 168.9 (COOH), 107-138 (Ar), and 44.6 (CH2).

Synthesis of II

Yield: 67%. C11H11NO5: Calcd. (%): C 55.70, H 4.67, N 5.90; Found (%): C 55.24, H 4.03, N 5.42. FAB-MS (m/z) 238 (M + 1). IR ν 3372 (N-H), 1670 (C-N), 1581 (CO2)as, 1345 (CO2)s, Δν (CO2): 236 cm-1. 1H NMR (DMSO-d6, 300 MHz) 12.7 (s, COOH), 12.5 (s, COOH), 8.39 (s, NH), 7.07-7.59, (m, Ar) 3.51 (t, CH2 J: 3.42), 2.33 (t, CH2 J: 4.1). 13C NMR (DMSO-d6, 75 MHz) 173.2 (COOH), 168.8 (COOH), 142.4 (CONH), 109-140 (Ar), 40.4 (CH2), 35.2 (CH2).

Synthesis of III

Yield: 80%. C17H15NO5: Calcd. (%): C 65.17, H 4.83, N 4.47; Found (%): C 64.86, H 4.32, N 4.11. FAB-MS (m/z) 314 (M + 1). IR ν 3380 (N-H), 1686 (C-N), 1577 (CO2)as, 1361 (CO2)s, Δν (CO2): 216 cm-1. 1H NMR (DMSO-d6, 300 MHz) 12.6 (s, COOH), 12.2 (s, COOH), 8.43 (s, NH), 7.02-7.51 (m, Ar), 5.06 (q, CH, J: 8.8), 3.4 (d, CH2, J: 10.1). 13C NMR (DMSO-d6, 75 MHz) 171.4 (COOH), 170.0 (COOH), 144.1 (CONH), 111-138 (Ar), 61.2 (CH), 36.1 (CH2).

Synthesis of IV

Yield: 70%. C15H11NO5: Calcd. (%): C 63.16, H 3.89, N 4.91; Found (%): C 63.02, H 3.43, N 4.60. FAB-MS (m/z) 286 (M + 1). IR ν 3388 (N-H), 1672 (C-N), 1566 (CO2)as, 1371 (CO2)s, Δν (CO2): 195 cm-1. 1H NMR (DMSO-d6, 300 MHz) 12.3 (s, COOH), 11.8 (s, COOH), 8.52 (s, NH), 7.13-8.33 (m, Ar). 13C NMR (DMSO-d6, 75 MHz) 176.7 (COOH), 165.4 (COOH), 148.2 (CONH), 120-136 (Ar).

Synthesis of antimony complexes

Aqueous solution of SbCl3 was made by dissolving 0.5 g (2.19 mM) in 10 mL, and a few drops of dil. HCl were added; to this solution, equimolar amount of ligand 2.19 mM, i.e. 0.48 g, 0.52 g, 0.69 g, and 0.62 g, respectively, for I-IV dissolved in ethanol (20 mL). The mixture was stirred at room temperature for 15 min, for adjustment of pH, and one drop of ammonia was added which resulted in the formation of a precipitate. The precipitate was filtered and washed with warm 70% ethanol and recrystallized from water.

Synthesis of V

Yield: 58%. C10H7ClNO5Sb: Calcd. (%): C 31.74, H 1.86, N 3.70, Sb 32.18; Found (%): C 31.21, H 1.45, N 3.39, Sb 31.80. FAB-MS (m/z) 377, 379 (M + 2). IR ν 3231 (N-H), 1655 (C-N), 1561 (CO2)as, 1320 (CO2)s, Δν (CO2): 241, 450 (N → Sb), 574 (O-Sb) cm-1. 1H NMR (DMSO-d6, 300 MHz) 8.24 (s, NH), 7.11-7.61 (m, Ar), 3.87 (s, CH2). 13C NMR (DMSO-d6, 75 MHz) 177.4 (CONH), 174.7 (COO), 170.2 (COO), 107-138 (Ar), 40.2 (CH2).

Synthesis of VI

Yield: 58%. C11H9ClNO5Sb: Calcd. (%): C 33.67, H 2.31, N 3.57, Sb: 31.03; Found (%): C 33.28, H 2.08, N 3.19, Sb: 30.67. FAB-MS (m/z) 391, 393 (M + 2). IR ν 3265 (N-H), 1643 (C-N), 1551 (CO2)as, 1302 (CO2)s, Δν (CO2): 249, 442 (N → Sb), 582 (O-Sb) cm-1. 1H NMR (DMSO-d6, 300 MHz) 12.7 (s, COOH), 12.5 (s, COOH), 8.39 (s, NH), 7.07-7.59, (m, Ar) 3.51 (t, CH2 J: 3.42), 2.33 (t, CH2 J: 4.1). 13C NMR (DMSO-d6, 75 MHz) 181.4 (CONH), 170.0 (COO), 160.1 (COO), 122-142 (Ar), 33.3 (CH2NH), 27.1 (CH2).

Synthesis of VII

Yield: 51%. C17H13ClNO5Sb: Calcd. (%): C 43.58, H 2.80, N 2.99, Sb 25.99; Found (%): C 43.20, H 2.50, N 2.67, Sb 25.34. FAB-MS (m/z) 467, 469 (M + 2). IR ν 3276 (N-H), 1666 (C-N), 1540 (CO2)as, 1311 (CO2)s, Δν (CO2): 229, 425 (N → Sb), 580 (O-Sb) cm-1. 1H NMR (DMSO-d6, 300 MHz) 8.24 (s, NH), 7.10-8.1 (m, Ar), 5.06 (t, CH, J: 9.7), 3.42 (d, CH2, J: 9.3). 13C NMR (DMSO-d6, 75 MHz) 180.6 (CONH), 174.0 (COO), 169.5 (COO), 125-136 (Ar), 66.8 (CH), 30.6 (CH2).

Synthesis of VIII

Yield: 58%. C15H9ClNO5Sb: Calcd.(%): C 40.90, H 2.06, N 3.18, Sb 27.64; Found (%):C 40.71, H 1.89, N 2.91, Sb 27.22. FAB-MS (m/z) 439, 441 (M + 2). IR ν 3266 (N-H), 1678 (C-N), 1541 (CO2)as, 1336 (CO2)s, Δν (CO2): 137, 446 (N → Sb), 568 (O-Sb) cm-1. 1H NMR (DMSO-d6, 300 MHz) 8.16 (s, NH), 7.06-8.55 (m, Ar). 13C NMR (DMSO-d6, 75 MHz) 183.2 (CONH), 170.4 (COO), 172.8 (COO), 123-137 (Ar).

Anti-leishmanial activity

Anti-leishmanial activity of the compound was carried out on the pre-established cultures of L. major (JISH118), L. major (MHOM/PK/88/DESTO), L. tropica (K27), L. infantum (LEM3437), L. mex mex (LV4) and L. donovani (H43). Parasites were cultured in medium M199 with 10% foetal bovine serum; 25 mM of HEPES, and 0.22 μg of penicillin and streptomycin, respectively at 24°C in an incubator. 1 mg of each test compound (I-VIII) was dissolved in 1 mL of water, ethanol, methanol and DMSO according to their solubilities. 1 mg of Amphotercin B was also dissolved in 1 mL of DMSO as reference drug. Parasites at log phase were centrifuged at 3000 rpm for 3 min. Parasites were diluted in fresh culture medium to a final density of 2 × 106 cells/mL. In 96-well plates, 180 μL of medium was added in different wells. 20 μL of the extracts was added in medium and serially diluted. 100 μL of parasite culture was added in all the wells. Four rows left for negative and positive controls: water, ethanol, methanol and DMSO, respectively, serially diluted in medium whereas positive control contained varying concentrations of standard antileishmanial compound, i.e. AmphotericinB. The plates were incubated for 72 h at 24°C. Results were analyzed through dose versus response by using nonlinear regression curve fit with Graphad Prims5.

Anti-fungal activity

Agar tube dilution method was used for screening antifungal activities against Aspergillus Flavus, Aspergillus Fumigants, Aspergillus Niger, and Fusarium Solani. A sample of Media supplemented with DMSO and reference antifungal drugs was used as negative and positive control, respectively. Tubes were then incubated at 27°C for 4-7 days and examined twice weekly during incubation. Standard drug, Miconazole, used for the above stated fungi, growth in media containing sample under test were determined by linear growth (mm) measuring, and percent inhibition of growth was calculated with reference to negative control using formula.

Results and discussion

Ligands 2-{[(carboxymethyl)amino]carbonyl}benzoic acid (I), 2-{[(2-carboxyethyl)amino]carbonyl}benzoic acid (II), 2-{[(1-carboxy-2-phenylethyl)amino]carbonyl}benzoic acid (III), and 2-[(4-carboxyanilino)carbonyl]benzoic acid (IV), and the complexes (V-VIII), all of which were synthesized using a general procedure as shown in Figure 1. Analytic data for the complexes confirmed the equimolar stoichiometries thereby tridentate ligation (ONO) of I-IV towards SbIII centre.

Figure 1
figure1

Synthesis (I-VIII) and pseudotrigonal bipyramidal geometry.

Full size image

FTIR spectra

Solid-state FTIR spectra were recorded in the spectral range of 4000-400 cm-1, and important vibrational frequencies were observed in this range. In the spectra of ligands (I-IV), characteristic broad band of carboxylic COOH functionality was observed in the range of 2800-3000 cm-1; OC-NH bond vibrated at 2600 cm-1; and aromatic C=C at 1500 cm-1 [16]. Broad band observed for carboxylic group disappeared in the spectra of complexes indicating deprotonation of ligand. In the spectra of compounds V-VIII, appearance of new band of medium intensity around 430 cm-1 indicated the coordination from N to antimony (O=C-NH → Sb) in pseudotrigonal bipyramidal arrangement (Figure 1) [17]. All the other bonds appeared at the same positions as in the spectra of the ligands ruling out coordination from carbonyl of phthalimido groups (Figure 1).

Solution-state multinuclear NMR spectra

In the solution-state 1H and 13C NMR spectra of compounds (V-VIII), all the nuclei resonated at appropriate positions; in 1H NMR spectra, the disappearance of carboxylic protons confirmed deprotonation as observed in the FTIR spectra of ligands (I-IV). In addition, downfield shift of imine proton proved the coordinate linkage of imine group toward antimony center (-NH → Sb) [18]. Similarly, in 13C NMR spectra, carbonyl (C=O) adjacent to imine group resonated at downfield position compared with that of the ligands confirming coordination linakge of imine with antimony center; all these facts proved the 1:1 ligand to metal stoichiometry in pseudotrigonal bipyramidal geometry (Figure 1) [19–21]. Further, either of the carboxylic groups displayed different chemical shifts with carboxylic group attached to phenyl ring appeared slightly at high filed.

MS & TGA analysis

In the FAB MS spectra of complexes VI-VIII, base peak was observed at 245 m/z due to [O=C-O-(SbCl)-O-C=O]+ fragment. Molecular ion peaks of very low intensity were observed with M + 2 peaks for isotopic 123Sb were also seen. Based on the data obtained, fragmentation patterns for ligands I-IV (Figure 2a) and complexes V-VIII (Figure 2b) have been proposed [20]. During the TGA analyses, heating rates were suitably controlled at 10°C/min under a nitrogen atmosphere, and the weight loss was measured ranging from ambient temperature up to 700°C. The weight losses for all the complexes were calculated for the corresponding temperature ranges and are shown in Table 1. The metal percentages left as metal oxide residues were compared with those determined by analytic metal content determination. Complexes V-VIII exhibited a three-stage decomposition pattern; as a first step, beginning of the weight loss occurred at 180, 178, 171, and 182 C, respectively, because of the escape of one C1 atom; next step of decomposition started at 280°C and extended up to 545°C corresponding to the loss of rest of the ligand's components and formation of metal oxide [22].

Figure 2
figure2

MS fragmentation patterns.

Full size image
Table 1 Thermal analysis data of complexes V-VIII
Full size table

All attempts employing different sets of conditions to obtain single crystals of the synthesized complexes suitable for XRD failed.

Anti-leishmanial and anti-fungal activities

All the compounds I-VIII were tested in vitro for their bioavailabilities against five leishmanial strains, i.e., L. major (JISH118), L. major (MHOM/PK/88/DESTO), L. tropica (K27), L. infantum (LEM3437), L. mex mex (LV4), and L. donovani (H43); and four fungi, viz., Aspergillus Flavus, Aspergillus Fumigants, Aspergillus Niger, and Fusarium Solani with one reference drug Amphotericin B, and the results are given in Tables 2 and 3, respectively. In general all the complexes (V-VIII) showed weaker activity compared to ligands (I-IV) and the reference drugs, but the complex VIII showed significant activity comparable to reference drugs. The activities (IC50) of all the compounds I-VIII together with AmphotericinB have been pictorially presented in Figure 3, and it is evident from the plot that the compound VIII exhibited significant activity. In complex VIII, the presence of bulkier R group, i.e., one benzyl moiety may be responsible for enhancement in drug uptake, thereby resulting significant activity [23, 24].

Table 2 In vitro Anti-leishmanial effect (IC50 in μg/mL) of I-VIII and standard drug (AmphotericinB)
Full size table
Table 3 In vitro Anti-fungal Effect of I-VIII and Standard Drug (Miconazole)
Full size table
Figure 3
figure3

In vitro anti-leishmanial activity.

Full size image

Conclusions

AntimonyIII center in all the synthesized complexes is pseudotrigonal bipyramidal. Complex containing benzyl group displays noteworthy anti-leishmanial and anti-fungal effects. Proper understanding of exact relationship between structure and activity needs further research.

References

  1. 1.

    Castro JR, Mahon MF, Molloy KC: Aerosol-assisted CVD of antimony sulfide from antimony dithiocarbamates. Chem Vapor Depos 2006, 12: 601–607. 10.1002/cvde.200506369

  2. 2.

    Chung JS: Acid-base and catalytic properties of metal compounds in the preparation of polyethylene terephthalate). J Macromol Sci A 1990, 27: 479–490.

  3. 3.

    Biros SM, Bridgewater BM, Estrada AV, Tanski JM, Parkin G: Antimony ethylene glycolate and catecholate compounds: structural characterization of polyesterification catalysts. Inorg Chem 41: 4051–4057.

  4. 4.

    Tanski JM, Kelly BV, Parkin G: Multidentate aryloxide and oxo-aryloxide complexes of antimony: synthesis and structural characterization of [η4 -N( o -C 6 H 4 O) 3 ]Sb(OSMe 2 ), {{[η3 -N( o -C 6 H 4 OH)( o -C 6 H 4 O) 2 ]Sb} 2 (μ 2 -O)} 2 and {[η3 -PhN( o -C 6 H 4 O) 2 ]Sb} 4 (μ 3 -O) 2 . Dalton Trans 2005, 2442–2447.

  5. 5.

    Kovaleva EV, Zemnukhova LA, Nikitin VM, Koryakova MD, Speshneva NV: Biological properties of Antimony(III) fluoride complexes. Russ J Appl Chem 2002, 75: 954–958. 10.1023/A:1020392814568

  6. 6.

    Dostál L, Jambor R, Ruzika A, Jirasko R, Cisarova I, Holecek J: The synthesis of organoantimony(III) difluorides containing Y,C,Y pincer type ligands using organotin(IV) fluorinating agents. J Fluor Chem 2008, 129: 167–172. 10.1016/j.jfluchem.2007.10.003

  7. 7.

    Gebel T: Arsenic and antimony: comparative approach on mechanistic toxicology. Chem Biol Interact 1997, 107: 131–144. 10.1016/S0009-2797(97)00087-2

  8. 8.

    Cantos G, Barbieri CL, Iacomini M, Gorin PAJ, Travassos LR: Synthesis of antimony complexes of yeast mannan and mannan derivatives and their effect on Leishmania-infected macrophages. Biochem J 1993, 289: 155–160.

  9. 9.

    Sharutin VV, Sharutina OK, Pakusina AP, Platonova TP, Fukin GK, Zakharov LN: Synthesis and structure of triphenylantimony dipropionate. Russ J Coord Chem 2001, 27: 368–370. 10.1023/A:1011306531669

  10. 10.

    Barucki H, Coles SJ, Costello JF, Gelbrich T, Hursthouse MB: Characterising secondary bonding interactions within triaryl organoantimony(V) and organobismuth(V) complexes. J Chem Soc Dalton Trans 2000, 2319–2325.

  11. 11.

    Sharutin VV, Sharutina OK, Bonsae EA, Pakusina AP, Gatilov YuV, Adonin NYu, Starichenko VF: Tetra- and triarylantimony fluorobenzoates: synthesis and structures. Russ J Coord Chem 2000, 28: 333–340.

  12. 12.

    Kasuga NC, Onodera K, Nakano S, Hayashi K, Nomiya K: Syntheses, crystal structures and antimicrobial activities of 6-coordinate antimony(III) complexes with tridentate 2-acetylpyridine thiosemicarbazone, bis(thiosemicarbazone) and semicarbazone ligands. J Inorg Biochem 2006, 100: 1176–1186. 10.1016/j.jinorgbio.2006.01.037

  13. 13.

    Sharutin VV, Sharutina OK, Panova LP, Platonova TP, Pakusina AP, Beľkii VK: Synthesis and structure of tri- p -tolylantimony ditosylate. Russ J Gen Chem 2002, 72: 229–231. 10.1023/A:1015469517544

  14. 14.

    Perrin DD, Armengo ELF: Purification of laboratory chemicals. Pergamon, Oxford, UK; 1988.

  15. 15.

    Mendham J, Denney RC, Barnes JD, Thomas M, (eds): Vogel's text book of quantitative chemical analysis. Pearson Education Pvt. Ltd., Singapore; 2003.

  16. 16.

    Dianzhong F, Bo W: Complexes of cobalt(II), nickel(II), copper(II), zinc(II) and manganese(II) with tridentate Schiff base ligand. Trans Met Chem 1993, 18: 101–103. 10.1007/BF00136062

  17. 17.

    Chunyan G, Xiaofang M, Jinlei T, Dongdong L, Shiping Y: Synthesis, structure, and DNA binding of three reduced aminoacid Schiff-base zinc(II), nickel(II), and cadmium(II) complexes. J Coord Chem 2010, 63: 115–123. 10.1080/00958970903311773

  18. 18.

    Machuč L, Dostál L, Jambor R, Handlíř K, Jirásko R, Růžička A, Císařová I, Holeček J: Intramolecularly coordinated organoantimony(III) carboxylates. J Organomet Chem 2007, 692: 3969–3975. 10.1016/j.jorganchem.2007.06.005

  19. 19.

    Liu Y, Tiekink ERT: Supramolecular associations in binary antimony(III) dithiocarbamates: influence of ligand steric bulk, influence on coordination geometry, and competition with hydrogen-bonding. Cryst Eng Commun 2005, 7: 20–27.

  20. 20.

    Li JS, Ma YQ, Cui JR, Wang RQ: Synthesis and in vitro antitumor activity of some tetraphenylantimony derivatives of exo -7-oxa-bicyclo[2,2,1] heptane (ene)-3-arylamide-2-acid. Appl Organomet Chem 2001, 15: 639–645. 10.1002/aoc.200

  21. 21.

    Mahajan K, Swami M, Singh RV: Microwave synthesis, spectral studies, antimicrobial approach, and coordination behavior of antimony(III) and bismuth(III) compounds with benzothiazoline. Russ J Coord Chem 2009, 35: 179–185. 10.1134/S1070328409030038

  22. 22.

    Stefan SL: Thermal decomposition of some metal chelates of substituted hydrazopyrazolones. J Therm Anal 1994, 42: 1299–1312. 10.1007/BF02546938

  23. 23.

    Croft SL, Sundar S, Fairlamb AH: Drug resistance in leishmaniasis. Clin Microbiol Rev 2006, 19: 111–126. 10.1128/CMR.19.1.111-126.2006

  24. 24.

    Kuryshev YA, Wang Lu, Wible BA, Wan X, Ficker E: Antimony-based antileishmanial compounds prolong the cardiac action potential by an increase in cardiac calcium currents. Mol Pharmacol 2006, 69: 1216–1225. 10.1124/mol.105.019281

Download references

Author information

Affiliations

  1. Department of Chemistry, Kohat University of Science & Technology, Kohat, 26000, Khyber Pakhtunkhwa, Pakistan

    • MI Khan
    • , Saima Gul
    • , Iqbal Hussain
    •  & Murad Ali Khan

  2. Department of Chemistry, The Islamia University of Bahawalpur, Bahawlpur, Punjab, Pakistan

    • Muhammad Ashfaq

  3. Faculty of Biological Sciences, Quaid-i-Azam University, Islamabad, Pakistan

    • Inayat-Ur-Rahman

  4. Institute of Pharmaceutical Sciences, Kohat University of Science and Technology, Kohat, 26000, Khyber Pakhtunkhwa, Pakistan

    • Farman Ullah

  5. Department of Chemistry, Gomal University, Dera Ismail Khan, Khyber Pakhtunkhwa, Pakistan

    • Gulrez Fatima Durrani
    • , Imam Bakhsh Baloch
    •  & Rubina Naz

Authors

  1. Search for MI Khan in:

  2. Search for Saima Gul in:

  3. Search for Iqbal Hussain in:

  4. Search for Murad Ali Khan in:

  5. Search for Muhammad Ashfaq in:

  6. Search for Inayat-Ur-Rahman in:

  7. Search for Farman Ullah in:

  8. Search for Gulrez Fatima Durrani in:

  9. Search for Imam Bakhsh Baloch in:

  10. Search for Rubina Naz in:

Corresponding author

Correspondence to MI Khan.

Additional information

Competing interests

The authors declare that they have no competing interests.

Authors’ original submitted files for images

Below are the links to the authors’ original submitted files for images.

Authors’ original file for figure 1

Authors’ original file for figure 2

Authors’ original file for figure 3

Rights and permissions

Open Access This article is distributed under the terms of the Creative Commons Attribution 2.0 International License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Reprints and Permissions

About this article

Keywords

  • antimony(III) carboxylates
  • anti-leishmanial
  • anti-fungal