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Synthesis, Structural and Biological Studies of Organotin(IV) Complexes with N-(Dithiocarboxy) Sarcosine

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Abstract

Five organotin complexes with general formulae [LCSSSnR2]n (R = Me, n-Bu, Ph) and R3SnLCSSSnR3 (R = n-Bu, Ph) were synthesized by the reaction of equimolar quantities of sarcosine (HLH) with KOH, CS2 and either R2SnCl2 (R = Me, n-Bu, Ph) or R3SnCl (R = n-Bu, Ph) in methanol. Elemental (CHNS) analyses data and mass spectroscopy agreed well with the molecular composition of the synthesized products. FTIR spectroscopy verified the monodentate binding mode of the carboxylate group and a bidentate chelating behavior of the dithiocarboxylate moiety of the ligand for binding with tin(IV). Thus, penta- and hexa-coordinated environments around tin were observed in the solid state in di- and triorganotin complexes, respectively. The penta-coordinated geometry in diorganotin(IV) product 2 was further verified by its single-crystal XRD analysis. The organotin moieties and ligand units were interconnected with each other alternately in hexameric cyclic arrangement. The number of protons found in 1H NMR spectra was in good agreement with those calculated by incremental method. Complexes were examined for their antioxidant, antimicrobial, antidiabetic, thrombolytic, hemolytic activities. The free ligand HLH was found inactive against all the four bacterial strains.

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References

  1. Iqbal, M.; Ali, S.; Haider, A.; Khalid, N.: Therapeutic properties of organotin complexes with reference to their structural and environmental features. Rev. Inorg. Chem. 37(2), 51–70 (2017)

    Article  Google Scholar 

  2. Ghazi, D.; Rasheed, Z.; Yousif, E.: Review of organotin compounds: chemistry and applications. Int. J. Res. Eng. Innov. 2(4), 340–348 (2018)

    Google Scholar 

  3. Jain, M.; Singh, V.; Singh, R.: Biologically potent sulphonamide imine complexes of organotin (IV): synthesis, spectroscopic characterization and biological screening. J. Iran. Chem. Soc. 1(1), 20–27 (2004)

    Article  Google Scholar 

  4. Javed, F.; Sirajuddin, M.; Ali, S.; Khalid, N.; Tahir, M.N.; Shah, N.A.; Rasheed, Z.; Khan, M.R.: Organotin (IV) derivatives of o-isobutyl carbonodithioate: synthesis, spectroscopic characterization, X-ray structure, HOMO/LUMO and in vitro biological activities. Polyhedron 104, 80–90 (2016)

    Article  Google Scholar 

  5. Saeed, A.; Channar, P.A.; Larik, F.A.; Jabeen, F.; Muqadar, U.; Saeed, S.; Flörke, U.; Ismail, H.; Dilshad, E.; Mirza, B.: Design, synthesis, molecular docking studies of organotin-drug derivatives as multi-target agents against antibacterial, antifungal, α-amylase, α-glucosidase and butyrylcholinesterase. Inorg. Chim. Acta 464, 204–213 (2017)

    Article  Google Scholar 

  6. Hadi, S.; Noviany, N.; Rilyanti, M.: In vitro antimalarial activity of some organotin (IV) 2-nitrobenzoate compounds against Plasmodium falciparum. Maced. J. Chem. Chem. En. 37(2), 185–191 (2018)

    Google Scholar 

  7. Ali, S.; Shahzadi, S.: Anticarcinogenicity and toxicity of organotin (IV) complexes: a review. Iran. J. Sci. Technol. A 42(2), 505–524 (2018)

    Article  Google Scholar 

  8. Adeyemi, J.; Onwudiwe, D.: Organotin (IV) dithiocarbamate complexes: chemistry and biological activity. Molecules 23(10), 2571 (2018)

    Article  Google Scholar 

  9. Hussain, S.; Ali, S.; Shahzadi, S.; Nawaz, M.; Ramzan, S.; Shahid, M.: Synthesis, spectroscopic characterization, X-ray crystal structure and biological activities of homo- and heterobimetallic complexes with. Polyhedron 119, 483–493 (2016). https://doi.org/10.1016/j.poly.2016.08.016

    Article  Google Scholar 

  10. Hussain, S.; Ali, S.; Shahzadi, S.; Rizzoli, C.; Shahid, M.: Diorganotin(IV) complexes with monohydrate disodium salt of iminodiacetic acid: synthesis, characterization, crystal structure and biological activities. J. Chin. Chem. Soc. 62(9), 793–802 (2015). https://doi.org/10.1002/jccs.201500274

    Article  Google Scholar 

  11. Yousif, E.; Mehdi, B.I.; Yusop, R.; Salimon, J.; Salih, N.; Abdullah, B.M.: Synthesis, structure and antibacterial activity of some triorganotin (IV) complexes with a benzamidoalanine ligand. J. Taibah Univ. Sci. 8(3), 276–281 (2014)

    Article  Google Scholar 

  12. Ghazi, D.; Yousif, E.: Design of organotin (IV) complexes derived from ciprofloxacin. Int. J. Res. Eng. Innov. 1(4), 63–65 (2017)

    Google Scholar 

  13. Mariam, S.; Hussain, S.; Ali, S.; Shahzadi, S.; Ramzan, S.; Shahid, M.: Homobimetallic (Sn, Sn) complexes with [2-dithiocarboxy (methyl) amino] acetic acid: synthesis, characterization and biological studies. Iran. J. Sci. Technol. A 42(3), 1277–1284 (2018)

    Article  Google Scholar 

  14. Alama, A.; Tasso, B.; Novelli, F.; Sparatore, F.: Organometallic compounds in oncology: implications of novel organotins as antitumor agents. Drug Disc. Today 14(9–10), 500–508 (2009)

    Article  Google Scholar 

  15. Nath, M.; Pokharia, S.; Yadav, R.: Organotin (IV) complexes of amino acids and peptides. Coord. Chem. Rev. 215(1), 99–149 (2001)

    Article  Google Scholar 

  16. Baul, T.S.B.; Kehie, P.; Duthie, A.; Guchhait, N.; Raviprakash, N.; Mokhamatam, R.B.; Manna, S.K.; Armata, N.; Scopelliti, M.; Wang, R.: Synthesis, photophysical properties and structures of organotin-Schiff bases utilizing aromatic amino acid from the chiral pool and evaluation of the biological perspective of a triphenyltin compound. J. Inorg. Biochem. 168, 76–89 (2017)

    Article  Google Scholar 

  17. Singh, N.; Kumar, K.; Srivastav, N.; Singh, R.; Kaur, V.; Jasinski, J.P.; Butcher, R.J.: Exploration of fluorescent organotin compounds of α-amino acid Schiff bases for the detection of organophosphorous chemical warfare agents: quantification of diethylchlorophosphate. New J. Chem. 42(11), 8756–8764 (2018)

    Article  Google Scholar 

  18. Lara-Cerón, J.A.; Jiménez-Pérez, V.M.; Molina-Paredes, A.A.; Rasika Dias, H.; Chávez-Reyes, A.; Ram Paudel, H.; Ochoa, M.E.; Muñoz-Flores, B.M.: Luminescent silk fibroin with organotin compounds from amino acid schiff bases–microwave-assisted synthesis, chemo-optical characterization, cytotoxicity, and confocal microscopy. Eur. J. Inorg. Chem. 2017(21), 2818–2827 (2017)

    Article  Google Scholar 

  19. Selvaganapathy, M.; Raman, N.: Pharmacological activity of a few transition metal complexes: A short review. J. Chem. Biol. Ther. 1(02), 2572-0406 (2016)

    Article  Google Scholar 

  20. Ueland, P.M.; Midttun, Ø.; Windelberg, A.; Svardal, A.; Skålevik, R.; Hustad, S.: Quantitative profiling of folate and one-carbon metabolism in large-scale epidemiological studies by mass spectrometry. Clin. Chem. Lab. Med. 45(12), 1737–1745 (2007)

    Article  Google Scholar 

  21. Perry, K.W.; Falcone, J.F.; Fell, M.J.; Ryder, J.W.; Yu, H.; Love, P.L.; Katner, J.; Gordon, K.D.; Wade, M.R.; Man, T.: Neurochemical and behavioral profiling of the selective GlyT1 inhibitors ALX5407 and LY2365109 indicate a preferential action in caudal vs cortical brain areas. Neuropharmacology 55(5), 743–754 (2008)

    Article  Google Scholar 

  22. Zhang, H.X.; Hyrc, K.; Thio, L.L.: The glycine transport inhibitor sarcosine is an NMDA receptor co-agonist that differs from glycine. J. Physiol. 587(13), 3207–3220 (2009)

    Article  Google Scholar 

  23. Khoo, L.E.; Goh, N.K.; Eng, G.; Whalen, D.J.; Hazell, A.: Synthesis, characterization and fungicidal activity of triphenyltin derivatives of sarcosine: crystal structures of [Ph3Sn (OCOCH2NH2CH3)2] Cl and [Ph3Sn (OCOCH2NH2CH3)2] NCS. Appl. Organomet. Chem. 9(8), 699–706 (1995)

    Article  Google Scholar 

  24. Hussain, S.; Bukhari, I.H.; Ali, S.; Shahzadi, S.; Shahid, M.; Munawar, K.S.: 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. (2015). https://doi.org/10.1080/00958972.2014.994515

    Article  Google Scholar 

  25. Arafat, Y.; Ali, S.; Shahzadi, S.; Shahid, M.: Preparation, characterization, and antimicrobial activities of bimetallic complexes of sarcosine with Zn (II) and Sn (IV). Bioinorg. Chem. Appl. 2013, 1–7 (2013)

    Article  Google Scholar 

  26. Chai, C.; Armarego, W.: Purification of laboratory chemicals, 5th edn. Butterworth Heinemann, Oxford (2003)

    Google Scholar 

  27. Hussain, S.; Ali, S.; Shahzadi, S.; Sharma, S.K.; Qanungo, K.; Shahid, M.; Jabbar, A.; Bukhari, I.H.: Organotin(IV) complexes with 5-aminoisophthalic acid: synthesis, characterization, theoretical study, and biological activities. Russ. J. Gen. Chem. 85(10), 2386–2394 (2015). https://doi.org/10.1134/S1070363215100266

    Article  Google Scholar 

  28. Khaliq, M.; Riaz, M.; Kanwal, N.; Mahmood, I.; Khan, A.; Bokhari, T.H.; Afzal, M.: Evolution of cytotoxicity, antioxidant, and antimicrobial studies of sugarcane (Saccharum officinarum) roots extracts. J. Chem. Soc. Pak. 39(1), 152–160 (2017)

    Google Scholar 

  29. Idrees, S.; Sarfraz, R.A.; Riaz, M.; Khera, R.A.; Zia, A.; Hanif, M.A.; Suleman, M.: Evaluation of antidiabetic, antioxidant, antimicrobial and cytotoxicity properties of avena sativa roots extracts. Oxid. Commun. 40(2), 613–623 (2017)

    Google Scholar 

  30. Riaz, M.; Rasool, N.; Bukhari, I.; Shahid, M.; Zubair, M.; Rizwan, K.; Rashid, U.: In vitro antimicrobial, antioxidant, cytotoxicity and GC-MS analysis of Mazus goodenifolius. Molecules 17(12), 14275–14287 (2012)

    Article  Google Scholar 

  31. Hussain, S.; Ali, S.; Shahzadi, S.; Tahir, M.N.; Shahid, M.: Synthesis, characterization, biological activities, crystal structure and DNA binding of organotin (IV) 5-chlorosalicylates. J. Coord. Chem. 68(14), 2369–2387 (2015)

    Article  Google Scholar 

  32. Riaz, M.; Rasool, N.; Bukhari, I.; Zubair, M.; Shahid, M.; Bokhari, T.; Gull, Y.; Rizwan, K.; Iqbal, M.; Zia-Ul-Haq, M.: Antioxidant studies using sunflower oil as oxidant substrate and protective assay by Antirrhinum majus. Oxid. Commun. 36(1), 272–282 (2013)

    Google Scholar 

  33. Lordan, S.; Smyth, T.J.; Soler-Vila, A.; Stanton, C.; Ross, R.P.: The α-amylase and α-glucosidase inhibitory effects of Irish seaweed extracts. Food Chem. 141(3), 2170–2176 (2013)

    Article  Google Scholar 

  34. Ali, M.S.; Amin, M.R.; Kamal, C.M.I.; Hossain, M.A.: In vitro antioxidant, cytotoxic, thrombolytic activities and phytochemical evaluation of methanol extract of the A. philippense L. leaves. Asian Pac. J. Trop. Biomed. 3(6), 464–469 (2013)

    Article  Google Scholar 

  35. PRO, A.C.: Agilent technologies, Yarnton, England (2012).

  36. Sheldrick, G.M.: A short history of SHELX. Acta Crystallogr. Sect. A Found. Crystallogr. 64(1), 112–122 (2008)

    Article  MATH  Google Scholar 

  37. Farrugia, L.J.: WinGX and ORTEP for Windows: an update. J. Appl. Crystallogr. 45(4), 849–854 (2012)

    Article  Google Scholar 

  38. Farrugia, L.J.: WinGX suite for small-molecule single-crystal crystallography. J. Appl. Crystallogr. 32(4), 837–838 (1999)

    Article  Google Scholar 

  39. Bonati, F.; Ugo, R.: Organotin (iv) n, n-disubstituted dithiocarbamates. J. Organomet. Chem. 10(2), 257–268 (1967)

    Article  Google Scholar 

  40. Javed, F.; Ali, S.; Shahzadi, S.; Sharma, S.K.; Qanungo, K.; Tahir, M.N.; Shah, N.A.; Khan, M.R.; Khalid, N.: Synthesis, structural characterization, theoretical calculations and in vitro biological activities of organotin (IV) complexes with [O, O] donor ligand. J. Inorg. Organomet. P. 26(1), 48–61 (2016)

    Article  Google Scholar 

  41. Hussain, S.; Ali, S.; Shahzadi, S.; Shahid, M.; Tahir, A.A.; Mustansar Abbas, S.; Riaz, M.; Ahmad, I.; Hussain, I.: Multinuclear (Sn/Pd) complexes with disodium 2, 2′-(dithiocarboxyazanediyl) diacetate hydrate; synthesis, characterization and biological activities. J. Coord. Chem. 70(24), 4070–4092 (2017)

    Article  Google Scholar 

  42. Tweedy, B.: Plant extracts with metal ions as potential antimicrobial agents. Phytopathology 55, 910–914 (1964)

    Google Scholar 

  43. Parveen, B.; Bukhari, I.H.; Hussain, S.; Ali, K.G.; Shahid, M.: Synthesis and spectroscopic characterization of mononuclear/binuclear organotin (IV) complexes with 1H-1, 2, 4-triazole-3-thiol: comparative studies of their antibacterial/antifungal potencies. J. Serbian Chem. Soc. 80(6), 755–766 (2015)

    Article  Google Scholar 

  44. Shi, Y.; Zhang, B.-Y.; Zhang, R.-F.; Zhang, S.-L.; Ma, C.-L.: 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(23), 4125–4136 (2012)

    Article  Google Scholar 

  45. Bnouham, M.; Ziyyat, A.; Mekhfi, H.; Tahri, A.; Legssyer, A.: Medicinal plants with potential antidiabetic activity-A review of ten years of herbal medicine research (1990-2000). Int. J. Diabetes Metab. 14, 1–25 (2006)

    Article  Google Scholar 

  46. Ali, M.; Salim Hossain, M.; Islam, M.; Arman, S.I.; Sarwar Raju, G.; Dasgupta, P.; Noshin, T.F.: Aspect of thrombolytic therapy: a review. Sci. World J. 2014, 1–8 (2014)

    Google Scholar 

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Correspondence to Shabbir Hussain, Saqib Ali or Saira Shahzadi.

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Hussain, S., Ali, S., Shahzadi, S. et al. Synthesis, Structural and Biological Studies of Organotin(IV) Complexes with N-(Dithiocarboxy) Sarcosine. Arab J Sci Eng 45, 4785–4795 (2020). https://doi.org/10.1007/s13369-020-04496-5

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  • DOI: https://doi.org/10.1007/s13369-020-04496-5

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