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Homobimetallic (Sn,Sn) Complexes with [2-Dithiocarboxy(methyl)amino]acetic Acid: Synthesis, Characterization and Biological Studies

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Abstract

Four bis(organotin(IV)) carboxylates dithiocarboxylates of the general formulae R2(Cl)SnLCS2Sn(Cl)R2 and R3SnLCS2SnR3 have been synthesized by a room temperature reaction between sarcosine (LH), potassium hydroxide (KOH), carbon disulphide (CS2) and R2SnCl2/R3SnCl (where R = n-Bu, Ph) following 1:1:1:2 molar ratio in methanol. The synthesized products have been characterized by microanalysis and various spectroscopic (IR, 1H NMR) techniques. Elemental (C, H, N and S) analysis data agreed well with the molecular composition of the products. FT-IR data indicated a bidentate binding mode of both the carboxylate and dithiocarboxylate donor regions of the ligand and penta-coordinated geometries around Sn(IV). 1H NMR spectroscopy demonstrates a stronger deshielding effect on the methylene protons of the ligand after complexation and flow of electronic charge density towards the metal centers. The de-shielding effect is more pronounced in chlorodiorganotin(IV) derivatives as compared to triorganotin(IV) derivatives. The complexes displayed significant antimicrobial potential depending upon the substitution pattern at tin(IV). The triorganotin(IV) derivatives generally exhibited a higher antibacterial/antifungal potential as compared to their dibutyltin(IV)/diphenyltin(IV) counterparts. The in vitro hemolytic activity investigations have shown that average lysis of human red blood cells caused by stannic products was significantly lower as compared to triton X-100 (positive control, 100 % lysis) and not very much higher than PBS (negative control, 0 % lysis). The chlorodibutyltin(IV) derivative 1 had shown the lower activity than its tri-analog 3 but chlorodiphenyltin(IV) derivative 2 had shown comparatively higher hemolytic effects than its tri-analog 4.

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References

  • Adan AB, Hayam MAA, Aida AG (2005) Novel pyrazole derivatives as potential promising anti-inflammatory antimicrobial agents. Arch Pharm 338:167–174

    Article  Google Scholar 

  • Arena G, Cali R, Contino A, Mususmeci A, Musumeci S, Purello R (1995) Coordination properties of dialkyltin (IV) in aqueous solution. Thermodynamic study of dimethyltin (IV) complexes with l-amino acids. Inorg Chim Acta 237:187–191

    Article  Google Scholar 

  • Armarego WLF, Chai CLL (2003) Purification of laboratory chemicals, 5th edn. Butterworth Heinemann, London

    Google Scholar 

  • Baul TSB, Dhar S, Kharbani N, Pyke SM, Butcher R, Smith FE (1999) The synthesis and structural characterization of some triorganotin (IV) complexes of 5-(4-chlorophenylazo) salicylic acid: crystal and molecular structure of triphenyltin 5-(4-chlorophenylazo) salicylate. Main Group Met Chem 22:413–421

    Article  Google Scholar 

  • Bonati F, Ugo R (1967) Organotin(IV) N, N-disubstituted dithiocarbamates. J Organomet Chem 10:257–268

    Article  Google Scholar 

  • Buttgereit F, Burmester GR, Simon LS (2001) Gastrointestinal toxic side effect of nonsteroidal ant-inflammatory drugs and cyclo-oxygenase-2- specific inhibitor. Am J Med 110:13–19

    Article  Google Scholar 

  • Clive PP, Michael JC, Morley S, Michael W, Brian H (1998) Integrated pharmacology. Elsevier, Amsterdam

    Google Scholar 

  • CLSI (The Clinical Laboratory Standards Institute) (2007) Agar dilution and disk diffusion susceptibility testing of Campylobacter spp. J Clin Microbiol 45:2758–2759

    Article  Google Scholar 

  • Eng G, Song X, Zapata A, de Dios AC, Casabianca L, Pike RD (2007) Synthesis, structural and larvicidal studies of some triorganotin 2-(p-chlorophenyl)-3-methylbutyrates. J Organomet Chem 692:1398–1404

    Article  Google Scholar 

  • Gao HM, Hong JS (2008) Why neurodegenerative diseases are progressive: uncontrolled inflammation drives disease progression. Trends Immunol 29:357–365

    Article  Google Scholar 

  • Hussain S, Ali S, Shahzadi S, Sharma SK, Qanungo K, Altaf M, Evans HS (2011) Synthesis, characterization, and semi-empirical study of organotin(IV) complexes with 4-(hydroxymethyl)piperidine-1-carbodithioic acid: X-ray structure of chlorodimethyl-(4-hydroxymethyl piperidine-1-carbodithioato-S, S’)tin(IV). Phosphorus Sulfur Silicon Relat Elem 186:542–551

    Article  Google Scholar 

  • Hussain S, Ali S, Shahzadi S, Sharma SK, Qanungo K, Bukhari IH (2012) Homobimetallic complexes containing Sn(IV) with acetylene dicarboxylic acid: their syntheses and structural interpretation by spectroscopic, semi-empirical, and DFT techniques. J Coord Chem 65:278–285

    Article  Google Scholar 

  • Hussain S, Ali S, Shahzadi S, Sharma SK, Qanungo K, Shahid M (2014) Synthesis, characterization, semiempirical and biological activities of organotin(IV) carboxylates with 4-piperidinecarboxylic acid. Bioinorg Chem Appl 2014:1–14

    Article  Google Scholar 

  • Hussain S, Bukhari IH, Ali S, Shahzadi S, Shahid M, Munawar KS (2015a) Synthesis and spectroscopic and thermogravimetric characterization of heterobimetallic complexes with Sn (IV) and Pd (II); DNA binding, alkaline phosphatase inhibition and biological activity studies. J Coord Chem 68:662–677

    Article  Google Scholar 

  • Hussain S, Ali S, Shahzadi S, Tahir MN, Shahid M (2015b) Synthesis, characterization, biological activities, crystal structure and DNA binding of organotin(IV) 5-chlorosalicylates. J Coord Chem 68:2369–2387

    Article  Google Scholar 

  • Javed F, Ali S, Shahzadi S, Sharma SK, Qanungo K, Tahir MN, Shah NA, Khan MR, Khalid N (2016) Potentially bioactive organotin(IV) complexes with [O, O] donor ligand: synthesis, structural elucidation N and biological screening. J Inorg Organomet Poly Met 26:48–61

    Article  Google Scholar 

  • Kana AT, Hibbert TG, Mahon MF, Molloy KC, Parkin IP, Price LS (2001) Organotin unsymmetric dithiocarbamates: synthesis, formation and characterisation of tin(II) sulfide films by atmospheric pressure chemical vapour deposition. Polyhedron 20:2989–2995

    Article  Google Scholar 

  • Klegeris A, McGeer PL (2005) Chymotrypsin-like proteases contribute to human monocytic THP-1 cell as well as human microglial neurotoxicity. Curr Alzheimer Res 2:355–365

    Article  Google Scholar 

  • Mansouri-Torshizi H, Moghaddam MI, Divsalar A, Saboury AA (2008) 2,2′-Bipyridinebutyldithiocarbamatoplatinum(II) and palladium(II) complexes: synthesis, characterization, cytotoxicity, and rich DNA-binding studies. Bioorg Med Chem 16:9616–9625

    Article  Google Scholar 

  • Mansouri-Torshizi H, Moghaddam MI, Divsalar A, Saboury AA (2009) Diimine platinum(II) and palladium(II) complexes of dithiocarbamate derivative as potential antitumor agents: synthesis, characterization, cytotoxicity, and detail dna-binding studies. J Biomol Struct Dyn 26:575–586

    Article  Google Scholar 

  • Moghaddam MI, Torshizi HM, Divsalar A, Saboury AA (2009) Synthesis, characterization, cytotoxic and DNA binding studies of diimine platinum(II) and palladium(II) complexes of short hydrocarbon chain ethyldithiocarbamate ligand. J Iran Chem Soc 6:552–569

    Article  Google Scholar 

  • Rehman A, Siddiqui SZ, Abbasi MA, Abbas N, Khan KM, Shahid M, Mahmood Y, Akhtar MN, Lajis NH (2012) Synthesis, antibacterial screening and hemolytic activity of S-substituted derivatives of 5-benzyl-1,3,4-oxadiazole-2-thiol. Int J Pharm Pharm Sci 4:676–680

    Google Scholar 

  • Sarker SD, Nahar L, Kumarasamy Y (2007) Microtitre plate-based antibacterial assay incorporating resazurin as an indicator of cell growth, and its application in the in vitro antibacterial screening of phytochemicals. Methods 42:321–324

    Article  Google Scholar 

  • Shahzadi S, Shahid K, Ali S (2007) Spectral characterization and biocidal activity of organotin(IV) (E)-3-[(2′,6′-dichlorophenylamido)]propenoates. J Coord Chem 60:2637–2648

    Article  Google Scholar 

  • Sharma P, Sharma JD (2001) In vitro hemolysis of human erythrocytes—by plant extracts with antiplasmodial activity. J Ethnophamacol 74:239–243

    Article  Google Scholar 

  • Sharma N, Kumar V, Kumari M, Pathania A, Chaudhry SC (2010) Synthesis, characterization, and antibacterial activity of triorganotin(IV) complexes of 2-methylphenol. J Coord Chem 63:3498–3515

    Article  Google Scholar 

  • Shi Y, Zhang BY, Zhang RF, Zhang SL, Ma CL (2012) Syntheses, characterizations, crystal structures, and in vitro antitumor activities of chiral triorganotin(IV) complexes containing (S)-(+)-2-(4-isobutyl-phenyl)propionic and (R)-(+)-2-(4-hydroxyphenoxy)propionic acid ligands. J Coord Chem 65:4125–4136

    Article  Google Scholar 

  • Singh R, Chaudhary P, Chauhan S, Swami M (2009) Microwave-assisted synthesis, characterization and biological activities of organotin (IV) complexes with some thio Schiff bases. Spectrochimica Acta Part A 72:260–268

    Article  Google Scholar 

  • Stiefel EI, Matsumoto K (1995) In transition metal sulfur chemistry. ASC symposium series. American Chemical Society, Washington

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, University of Sargodha, Lyallpur Campus, Faisalabad, Pakistan

    Sidra Mariam & Saira Shahzadi

  2. Department of Chemistry, GC University, Faisalabad, Pakistan

    Shabbir Hussain

  3. Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    Saqib Ali, Saira Shahzadi & Sadaf Ramzan

  4. Department of Chemistry and Biochemistry, University of Agriculture, Faisalabad, Pakistan

    Muhammad Shahid

Authors
  1. Sidra Mariam
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  2. Shabbir Hussain
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  3. Saqib Ali
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  4. Saira Shahzadi
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  5. Sadaf Ramzan
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  6. Muhammad Shahid
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Correspondence to Saqib Ali or Saira Shahzadi.

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Mariam, S., Hussain, S., Ali, S. et al. Homobimetallic (Sn,Sn) Complexes with [2-Dithiocarboxy(methyl)amino]acetic Acid: Synthesis, Characterization and Biological Studies. Iran J Sci Technol Trans Sci 42, 1277–1284 (2018). https://doi.org/10.1007/s40995-016-0127-3

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  • DOI: https://doi.org/10.1007/s40995-016-0127-3

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