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Synthesis, Spectroscopic and Antimicrobial Studies of Homo- and Heteronuclear Tin(IV)/Pd(II) Complexes of 2-Amino-6-(Dithiocarboxyamino)Hexanoic Acid

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Abstract

Homobimetallic organotin(IV) carboxylates dithiocarboxylates, Ph2SnLCS2Sn(Cl)Ph2 (1) and Ph3SnHLCS2SnPh3 (2) were synthesized by a room temperature reaction of l-lysine monohydrate (H2LH) with potassium hydroxide, carbon disulfide and Ph3SnCl/Ph2SnCl2 in methanol. Heterotrinuclear complexes (Bu2SnLCS2)2Pd (3) and (Bu2SnLCS2)2Pd (4) were also synthesized by a reaction of H2LH with KOH, CS2 and PdCl2(aq) in methanol followed by the treatment with n-Bu2SnCl2/Ph2SnCl2. The products were characterized by elemental analysis, FT-IR, multinuclear NMR (1H, 13C and 119Sn) and electron ionization mass spectroscopy (EIMS). The elemental analysis and mass spectrometry verified the molecular composition and structures of complexes. FT-IR spectroscopy demonstrated monodentate binding behavior of the carboxylate group and chelating mode of the dithiocarbamate moiety. The diorganotin(IV) derivatives 1, 3 and 4 convert their solid-state tetra-coordinated structures into trigonal bipyramidal arrangements in solution. However, triphenyltin(IV) derivative 2 exhibited penta-coordinated environment around Sn(IV) in the solid-state and tetrahedral configuration in the solution form. A square planar environment around Pd(II) was exhibited in the solid state. The investigated products displayed antibacterial/antifungal potential, and their minimal inhibitory concentrations (MIC) values were also demonstrated. The nature of the coordinated metals (Sn + Sn or Sn + Pd) and the substitution pattern at tin play a major role in biological actions of these products. The heterometallic (Pd, Sn) products possessed more potential against fungi than bacteria. The heterobimetallic dibutyltin(IV) complex 3 has shown the lowest hemolytic activity (10.76%), while its phenyltin(IV) counterpart 4 possessed the highest cytotoxicity (50.11%).

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Authors and Affiliations

  1. Department of Chemistry, Lahore Garrison University, DHA Phase VI, Lahore, Pakistan

    Shabbir Hussain & Zark Zahid

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

    Muhammad Shahid

  3. Department of Basic Sciences and Humanities, University of Engineering and Technology, Lahore, Narowal Campus, Lahore, Pakistan

    Muhammad Amin Abid

  4. School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, 430074, China

    Muhammad Amin Abid

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  1. Shabbir Hussain
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Hussain, S., Zahid, Z., Shahid, M. et al. Synthesis, Spectroscopic and Antimicrobial Studies of Homo- and Heteronuclear Tin(IV)/Pd(II) Complexes of 2-Amino-6-(Dithiocarboxyamino)Hexanoic Acid. Arab J Sci Eng 44, 6423–6434 (2019). https://doi.org/10.1007/s13369-019-03938-z

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