The discovery of the anticancer properties of cisplatin promoted a great deal of interest in the area of metal-based antitumor agents. With this aim, a new series of triorganotin(IV) derivatives: Ph3SnL (1), BZ3SnL (2), where L = morpholine-1-carbodithioate (MCDT) have been synthesized by the reaction of triorganotin(IV) chlorides with the ligand-salt in the appropriate molar ratio. All the complexes have been characterized by FT-IR, 1H, 13C, and 19Sn NMR spectroscopy. In addition, the molecular structure of complex 1 was determined by single crystal X-ray diffraction study. X-ray crystallographic analysis shows that in the compound [Ph3Sn(MCDT)], the Sn ion is in a four-coordinate environment with a dithiocarbamate ligand coordinated to the tin(IV) in a monodentate fashion through the sulfur atom. Furthermore, the cytotoxic activity of the free ligand (MCDT) as well as its triorganotin(IV) complexes were tested against tumor cell lines human cervix carcinoma HeLa, human myelogenous leukemia K562 and normal immunocompetent cells, peripheral blood mononuclear cells PBMC. The cytotoxic results indicate that coupling of MCDT with R3Sn(IV) metal center results in a complex with important biological properties and remarkable cytotoxic activity, since we observe IC50 values better to that of the antitumor drug cisplatin.
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Awang N, Yousef NSAM, Baba I, Fadilah Rajab N, Hamid A, Yamin BM, Abdul Halim A (2010) Synthesis and characterization of organotin (IV) N-Methyl-N Isopropyldithiocarbamate compounds: X-ray crystal structure of (CH3)2Sn[S2CN(CH3)(i-C3H7)]2. World Appl Sci J 9:804–810
Awang N, Baba I, Yamin BM, Sham Othman M, Abdul Halim A (2011) Synthesis, characterization and crystal structure of triphenyltin(IV) N-alkyl-N-cyclohexyldithiocarbamate compounds. World Appl Sci J 12:630–635
Cea-Olivares R, Gomez-Ortiz LA, Garcia-Montalvo V, Gavino Ramirez RL, Hernandez-Ortega S (2000) Formation of a novel trinuclear spirostannoxane tin(IV) compound. Crystal and molecular structure of [Sn(nBu)(Cl)[(OCH2CH2S)2Sn(nBu)]2] and the stannolane [(nBu)Sn(SCH2CH2O)SCH2CH2OH]. J Inorg Chem 39:2284–2288
Fuentes-Martinez JP, Toledo-Martinez I, Roman-Bravo P, Garcia P, Godoy-Alcantar C, Lopez-Cardoso M, Morales-Rojas H (2009) Diorganotin(IV) dithiocarbamate complexes as chromogenic sensors of anion binding. J Polyhedron 28(3953):3966
Gomez-Ruiz S, Kaluderovic GN, Prashar S, Hey-Hawkins E, Eric A, Ziazak Z, Juranic ZD (2008) Study of the cytotoxic activity of di and triphenyltin(IV) carboxylate complexes. J Inorg Biochem 102:2087–2096
Gomez-Ruiz S, Prashar S, Walther T, Fajardo M, Steinborn D, Paschke R, Kaluderovic GN (2010) Cyclopentadienyltin(IV) derivatives: synthesis, characterization and study of their cytotoxic activities. J Polyhedron 29:16–23
Hadjikakou SK, Hadjiliadis N (2009) Antiproliferative and anti-tumor activity of organotin compounds. Coord Chem Rev 253:235–249
Husain A, Nami SAA, Siddiqi KS (2010) Synthesis, characterization and biocidal activities of heterobimetallic complexes having tin(IV) as a padlock. J Mol Struct 970:117–127
Kalu Cerovi GN, Paschke R, Prashar S, Gómez-Ruiz S (2010) Synthesis, characterization and biological studies of 1-D polymeric triphenyltin(IV) carboxylates. J Organomet Chem 695:1883–1890
Khan S, Nami SAA, Siddiqi KS (2008) Mononuclear indolyldithiocarbamates of SnCl4 and R2SnCl2: spectroscopic, thermal characterizations and cytotoxicity assays in vitro. J Organomet Chem 693:1049–1057
Khan H, Badshah A, Murtaz G, Said M, Rehman Z, Neuhausen C, Todorova M, Jean-Claude BJ, Butler IS (2011) Synthesis, characterization and anticancer studies of mixed ligand vdithiocarbamate palladium(II) complexes. Eur J Med Chem 46:4071–4077
Menezes DC, Vieira FT, de Lima GM, Wardell JL, Cortés ME, Ferreira MP, Soares MA, Vilas Boas A (2008) The in vitro antifungal activity of some dithiocarbamate organotin(IV) compounds on Candida albicans—amodelforbiological interaction of organotin complexes. Appl Organomet Chem 22:221–226
Metsios A, Verginadis I, Simos Y, Batistatou A, Peschos D, Ragos V, Vezyraki P, Evangelou A, Karkabounas S (2012) Cytotoxic and anticancer effects of the triorganotin compound [(C6H5)3Sn(cmbzt)]: an in vitro, ex vivo and in vivo study. Eur J Pharm Sci 47:490–496
Moldeus T, Hogberg J, Orrhenius S, Fleischer S, Packer L (1978) Isolation and use of liver cells. Methods Enzymol 52:60–71
Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63
Ohno M, Abe T (1991) Rapid colorimetric assay for the quantification of leukemia inhibitory factor (LIF) and interleukin-6 (IL-6). J Immunol Methods 145:199–203
Rehman W, Kaleem Baloch M, Badshah A (2008) Synthesis, spectral characterization and bio-analysis of some organotin(IV) complexes. Eur J Med Chem 43:2380–2385
Rehman Z, Muhammad N, Shuja S, Ali S, Butler IS, Meetsma A, Khan M (2009a) New dimeric, trimeric and supramolecular organotin(IV) dithiocarboxylates: synthesis, structural characterization and biocidal activities. J Polyhedron 28:3439–3448
Rehman Z, Shah A, Muhammad N, Ali S, Qureshi R, Meetsma A, Butler IS (2009b) Synthesis, spectroscopic characterization, X-ray structure and evaluation of binding parameters of new triorganotin(IV) dithiocarboxylates with DNA. Eur J Med Chem 44:3986–3993
Rehman A, Hussain M, Rehman Z, Rauf A, Nasim FH, Tahir AA, Ali S (2010) New tetrahedral, square-pyramidal, trigonal-bipyramidal and octahedral organotin(IV) 4-ethoxycarbonylpiperazine-1-carbodithioates: synthesis, structural properties and biological applications. J Organomet Chem 695:1526–1532
Rehman Z, Muhammad N, Ali S, Butler IS, Meetsma A (2011) New mononuclear organotin(IV) 4-benzhydrylpiperazine-1-carbodithioates: synthesis, spectroscopic characterization, X-ray structures and in vitro antimicrobial activities. J Inorg Chim Acta 373:187–194
Sedaghat T, Jalilian F (2009) New adducts of diorganotin(IV) chlorides with a new multifunctional schiff baseligand: synthesis and spectral properties. J Iran Chem Soc 6:271–276
Shaheen F, Rehman Z, Ali S, Meetsma A (2012) Structural properties and antibacterial potency of new supramolecular organotin(IV) dithiocarboxylates. J Polyhedron 31:697–703
Shahzadi S, Ali S, Bhatti MH, Fettouhi M, Athar M (2006) Chloro-diorganotin(IV) complexes of 4-methyl-1-piperidine carbodithioic acid: synthesis, X-ray crystal structures, spectral properties and antimicrobial studies. J Organomet Chem 691:1797–1802
Sisido K, Takeda Y (1961) Direct synthesis of organotin compounds. I. Di- and tribenzyltin chloride. J Am Chem Soc 83:538–541
Tarassoli A, Sedaghat T, Neumuller B, Ghassemzadeh M (2001) Synthesis, spectroscopic investigations and crystal structures of organotin(IV) derivatives of 2-amino-1-cyclopentene-1-carbodithioic acid. J Inorg Chim Acta 318:15–22
Yin H, Wang C, Hong M, Wang D (2004) Synthesis, spectroscopic properties and crystal structures of SnBr2[S2CN(CH2CH2)2O]2, (4-F-C6H4CH2)2Sn(Cl)S2CN(CH2CH2)2O and (2-F-C6H4CH2)3SnS2CN(CH2CH2)2O. J Organomet Chem 689:1277–1283
Yousefi M, Safari M, Bikhof Torbati M, Molla Kazemiha V, Sanati H, Amanzadeh A (2012) New mononuclear diorganotin(IV) dithiocarboxylates: synthesis, characterization and study of their cytotoxic activities. J Appl Organomet Chem 26:438–444
The authors like to express their profound gratitude to the Azad University, Shahr-e-Rey Branch, Iran and National Cell Bank of Pasteur Institute of Iran for providing necessary research facilities and financial assistance. The authors also gratefully acknowledge the valuable help of Dr. Mohammad Ali Shokrgozar, head of National Cell Bank of Iran, Pasteur Institute of Iran.
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Safari, M., Yousefi, M., Jenkins, H.A. et al. Synthesis, spectroscopic characterization, X-ray structure, and in vitro antitumor activities of new triorganotin(IV) complexes with sulfur donor ligand. Med Chem Res 22, 5730–5738 (2013). https://doi.org/10.1007/s00044-013-0549-9
- Triorganotin (IV) complex
- Crystal structure
- NMR spectroscopy
- Antitumor activity
- Cell lines