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Original Articles

Synthesis, Spectroscopy and in vitro Cytotoxicity of New Hydroxyanthraquinonato Triorganotin CompoundsFootnote

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Pages 41-51 | Received 08 Oct 2006, Accepted 24 Nov 2006, Published online: 30 Mar 2007

References

  • Gielen , M. 1996 . Tin based antitumor drugs . Coord. Chem. Rev. , 151 : 41
  • Musmeci , M. T. , Madonia , G. , Lo Giudice , M. T. , Silvestri , A. , Ruisi , G. and Barbieri , R. 1992 . Interactions of organotins with biological sytems . Appl. Organometal. Chem. , 6 : 127
  • Pellerito , L. and Nagy , L. 2002 . Organotin (IV) complexes formed with biologically active ligands: equilibrium and structural studies, and some biological aspects . Coord. Chem. Rev. , 224 : 111
  • Ali , A. , Upreti , R. K. and Kidway , A. M. 1990 . Assessment of di‐ and tri‐butyltin interaction with skeletal muscle membranes . Bull. Environ. Contam. Toxicol. , 44 : 29
  • Cooke , G. M. 2002 . Effect of organotins on human aromatase activity in vitro . Toxicol. Lett. , 126 : 121
  • Osadaa , S. , Nishikawaa , J. , Nakanishi , T. , Tanakab , K. and Nishiharaa , T. 2005 . Some organotin compounds enhance histone acetyltransferase activity . Toxicol. Lett. , 155 : 329
  • Nakanishi , T. , Kohroki , J. , Suzuki , S. , Ishizaki , J. , Hiromori , Y. , Takasuga , S. , Itoh , N. , Watanabe , Y. , Utoguchi , N. and Tanaka , K. 2002 . Trialkyltin compounds enhance human CG secretion and aromatase activity in human placental choriocarcinoma cells . J. Clin. Endocrinol. Metab. , 87 ( 6 ) : 2830
  • Gielen , M. 2002 . Organotin compounds and their therapeutic potential: A report form the Organometallic Chemistry Department of the free University of Brussels . Appl. Organometal. Chem. , 16 : 481
  • Gielen , M. , Biesemans , M. and Willem , R. 2005 . Organotin compounds: from kinetics to stereochemistry and antitumour activities . Appl. Organometal. Chem. , 19 : 440
  • Gielen , M. , Biesemans , M. , de Vos , D. and Willem , R. 2000 . Synthesis, characterization and in vitro antitumor activity of di‐ and triorganotin derivatives of polyoxa‐and biologically relevant carboxylic acids . J. Inorg. Biochem. , 79 : 139
  • Gielen , M. , Willem , R. , Biesemans , M. , Boualam , M. , Khloufi , A El and de Vos , D. 1992 . Exceptionally high in vitro antitumor activity of substituted triphenyltin benzoates including salicylates against a human mammary tumor, MCF‐7, and a colon carcinoma, WiDr . Appl. Organometal. Chem. , 6 ( 3 ) : 287
  • Pruchnik , F. P. , Banbul , M. Ciunik , Z. 2003 . Structure, properties and cytostatic activity of tributyltin aminoarylcarboxylates . Inorg. Chim. Acta , 356 : 62
  • Szorcsik , A. , Nagy , L. , Sletten , J. , Szalontai , G. , Kamu , E. , Fiore , T. , Pellerito , L. and Kálmán , E. 2004 . Preparation and structural studies on dibutyltin(IV) complexes with pyridine mono‐ and dicarboxylic acids . J. Organometal. Chem. , 689 : 1145
  • Costa , L. C. M. , Limaa , G. M. , Maia , J. R. , Filgueiras , C. A. L. , Doriguetto , A. C. and Ellena , J. 2005 . The synthesis and characterization of Sn(IV) complexes of 2,6‐pyridine dicarboxylate—the molecular structure of divinyltin(IV) derivative . Spectra Acta Part A , 61 : 1971
  • Nath , M. , Pokharia , S. and Yadav , R. 2001 . Organotin (IV) complexes of amino acids and peptides . Coord. Chem. Rev. , 215 : 99
  • Mahon , M. F. , Molloy , K. C. , Omotowa , B. A. and Mesubi , M. A. 1996 . Organotin(IV) derivatives of acylpyrazol‐5‐ones . J. Organometal. Chem. , 511 : 227
  • Marchetti , F. , Pettinari , C. , Cingolani , A. , Gioia Lobbia , G. , Cassetta , A. and Luisa Barba , L. 1996 . Triorganotin(IV) derivatives of several 4‐acyl‐5‐pyrazolonato ligands: synthesis, spectroscopic characterization and behavior in solution. Crystal structure of aquotrimethyl(4‐p‐methoxybenzoyl‐1‐phenyl‐3‐methyl‐pyrazolon‐5‐ato) tin(IV) . J. Organometal. Chem. , 517 : 141
  • Pettinari , C. , Marchetti , F. , Cingolani , A. , Leonesi , D. , Mundorff , E. , Rossi , M. and Caruso , F. 1997 . Tin(IV) and organotin(IV) derivatives of novel b‐diketones. II Mono‐ and diaryltin (IV) complexes of l‐phenyl‐3‐methyl‐4‐R(C˭O)‐pyrazol‐5one (R˭CCl3, OCH3, C2H5). Crystal structure of trans‐dibenzylbis (l‐phenyl‐3‐methyl‐4‐methoxycarbonyl‐pyrazolon‐5‐ato)tin(IV),(C7H7)2 (sn(QomF)2 . Inorg. Chim. Acta. , 262 : 33
  • Pettinari , C. , Marchetti , F. , Cingolani , A. , Tanski , J. , Rossi , M. and Caruso , F. 1997 . Tin (IV) and organotin (IV) derivatives of novel 3‐diketones I. Dialkyltin (IV) complexes of l‐phenyl‐3‐methyl‐4‐R′ (C‐O)‐pyrazol‐5‐one (R′˭CCl3, O‐C2H5, O‐i‐C3H7, O‐C7H7). Crystal and molecular structure of trans‐dimethylbis [l‐phenyl‐3‐methyl‐4‐i‐propoxycarbonyl‐pyrazolon‐5‐ato]tin(IV) . Inorg. Chim. Acta. , 257 : 37
  • Pettinari , C. , Marchetti , F. , Cingolani , A. , Leonesi , D. , Mundorff , E. , Rossi , M. and Caruso , F. 1998 . Tin(IV) and organotin(IV) derivatives of novel b‐diketones. III1 Diorgano‐ and dihalotin(IV) complexes of 1,3‐dimethyl‐4‐R(C˭O)‐pyrazol‐5‐one (R˭CH3, C6H5) and the crystal structure of trans‐dicyclohexylbis(1,3‐dimethyl‐4‐acetylpyrazolon‐5‐ato)tin(IV) . J. Organometal. Chem. , 557 : 187
  • Marchetti , F. , Pettinari , C. , Cingolani , A. , Brocanelli , L. , Rossi , M. and Caruso , F. 1999 . Tin(IV) and organotin(IV) derivatives of novel b‐diketones Part IV. Triorganotin(IV) complexes of fluorinated 4‐acyl‐5‐pyrazolones. Crystal structure of (1‐(4‐trifluoromethylphenyl)‐3‐methyl‐4‐acetylpyrazolon‐5‐ato)‐triphenyltin(IV) . J. Organometal. Chem. , 580 : 344
  • Marchetti , F. , Pettinari , C. , Cingolani , A. , Brocanelli , L. , Rossi , M. and Caruso , F. 2002 . Organotin(IV) derivatives of novel diketones part V. Synthesis and characterization of di‐ and triorganatin(IV) derivatives of 4‐acyl‐5‐pyrazolones modified in position 3 of the pyrazole. Crystal structure of (1,3‐diphenyl‐4‐benzoyl‐pyrazolon‐5‐ato)triphenyltin(IV) . J. Organometal. Chem. , 645 : 134
  • Saxena , F. , Huber , F. , Pelleritot , L. and Girasolot , A. 1987 . Organoelement derivatives of steroids: Synthesis and structural features of organo‐ silicon, ‐tin and ‐lead derivatives of cholesterol and desoxycholic acid . Appl. Organometal. Chem. , 1 : 413
  • Kovala‐Demertzi , D. 2006 . Recent advances on non‐steroidal anti‐inflammatory drugs, NSAIDs: Organotin complexes of NSAIDs . J. Organometal. Chem. , 691 ( 8 ) : 1767
  • Maggio , F. , Pellerito , A. , Pellerito , L. , Grimaudo , S. , Mansueto , C. and Vitturi , R. 1994 . Organometallic complexes with biological molecules II. Synthesis, solid‐state characterization and in vivo cytotoxicity of diorganotin (IV) chloro and triorganotin (IV) chloro derivatives of Penicillin . G. Appl. Organometal. Chem. , 8 : 71
  • Jankovics , H. , Nagy , L. , Kele , Z. , Pettinari , C. , D'Agati , P. , Mansueto , C. , Pellerito , C. and Pellerito , L. 2003 . Coordination properties of the ACE inhibitor captopril towards Me2Sn(IV)2 in aqueous solution, and biological aspects of some dialkyltin(IV) derivatives of this ligand . J. Organometal. Chem. , 668 : 129
  • Davies , A. G. 2004 . Organotin Chemistry Wiley‐VCH .
  • Brown , M. , McGarvey , B. , Ozarowski , A. and Tuck , D. 1998 . Studies of organotin (IV)‐ orthoquinone systems . J. Organometal. Chem. , 550 : 165
  • Spyroudis , S. 2000 . Hydroxyquinones: synthesis and reactivity . Molecules , 5 : 1291
  • Beslija , S. 2003 . The role of anthracyclines/anthraquinones in metastatic breast cancer . Br. Cancer Res. Treat. , 81 ( Suppl.1 ) : 25
  • Sendelbach , L. E. 1989 . A review of the toxicity and carcinogenicity of anthraquinone derivatives . Toxicology , 57 ( 3 ) : 227
  • El‐Gogary , T. M. 2003 . Molecular complexes of some anthraquinone anti‐cancer drugs: experimental and computational study . Spectr. Acta Pt. A , 59 : 1009
  • Christianopoulou , M. , Ecateriniadou , L. and Sarris , K. 1986 . Evaluation of the antimicrobial activity of a new series of hydroxy‐quinone chelates of some transition metals . Eur. J. Med. Chem. , 21 : 385
  • Christianopoulou , M. , Akrivos , P. and Baumgarten , M. 1987 . Binuclear metal chelate complexes of anthraquinones having a MO4 chromophore. Part 1 . Quinizarin. Can. J. Chem. , 65 : 1485
  • Akrivos , P. , Christianopoulou , M. , Baumgarten , M. and Kokorotsikos , P. 1990 . Homobinuclear metal chelates of anthraquinones having a MO4 chromophore‐II . Anthrarufin. Spectr. Acta , 46A ( 3 ) : 363
  • Kawai , K. , Mori , H. and Sugie , S. 1986 . Genotoxicity in the hepatocyte/DNA repair test and toxicity to liver mitochondria of 1‐hydroxyanthraquinone and several dihydroxyanthraquinones . Cell Biol. Toxicol. , 2 ( 4 ) : 457
  • Giles , G. and Sharma , R. 2005 . Solid phase synthesis of anthraquinone peptides and their evaluation as topoisomerase I inhibitors . J. Pept. Sci. , 11 ( 7 ) : 417
  • Petke , J. D. , Butler , P. and Maggiora , G. M. 1985 . Quantum‐mechanical characterization of the electronic states of anthraquinone, quinizarin, and 1,4‐diamino anthraquinone . Int. J. Quant. Chem. , 27 : 71
  • Fain , V. , Zaitsev , B. E. and Ryabov , M. A. 2004 . Metal complexes with 1,5‐ and 1,8‐dihydroxy‐9,10‐anthraquinones: Electronic absorption spectra and structure of ligands . Russ. J. Coord. Chem. , 30 ( 5 ) : 360
  • Churchill , M. R. , Keil , K. M. and Bright , F. V. 2000 . Linkage and redox isomerism in ruthenium complexes of catecholate, semiquinone, and o‐acylphenolate ligands derived from 1,2‐dihydroxy‐9,10‐anthracenedione (alizarin) and related species: syntheses, characterizations, and photophysics . Inorg. Chem. , 39 : 5807
  • DelMedico , A. , Dodsworth , E. S. , Lever , A. B. P. and Pietro , W. J. 2004 . Electronic structure and spectra of linkage isomers of bis(bipyridine)(1,2‐dihydroxy‐9,10‐anthraquinonato)ruthenium(II) and their redox series . Inorg. Chem. , 43 : 2654
  • Sisido , K. , Takeda , Y. and Kinugawa , Z. 1960 . Direct synthesis of organtotin compounds. I. Di and tri‐benzyltin chlorides . J. Am. Chem. Soc. , 83 : 538
  • Skehan , P. , Storeng , R. , Scudiero , D. , Monks , A. , McMahon , J. , Vistica , D. , Warren , J. T. , Bokesch , H. , Kenney , S. and Boyd , M. R. 1990 . New colorimetric cytotoxicity assay for anticancer‐drug screening . J. Nat. Cancer Inst. , 82 ( 13 ) : 1107
  • Fain , V. , Zaitsev , B. E. and Ryabov , M. A. 2003 . Electronic absorption spectra and tautomerism of quinizarin and its substituted derivatives . Russ. J. Gen. Chem. , 73 ( 10 ) : 1595
  • Fain , V. , Zaitsev , B. E. and Ryabov , M. A. 2006 . Tautomeric and conformational isomerism of natural hydroxyanthraquinones . Chem. Nat. Prod. , 42 ( 3 ) : 269
  • Fain , V. , Zaitsev , B. E. and Ryabov , M. A. 2004 . Metal complexes with alizarin and alizarin red S: Electronic absorption spectra and structure of ligands . Russ. J. Coord. Chem. , 30 ( 5 ) : 365
  • Singh , R. V. , Joshi , S. C. , Gajraj , A. and Nagpal , P. 2002 . Studies of biologically potent organotin(IV) and organosilicon(IV) complexes of a sulfur donor ligand derived from 1‐acetylferrocene . Appl. Organometal. Chem. , 16 ( 12 ) : 713

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