Synthesis, Structure and In vitro Biological Activity of New Hydroxy‐Naphthoquinonato Triorganotin Compounds

References

• O'Brien , P. J. 1991 . Molecular mechanisms of quinone cytotoxicity . Chem. Biol. Interact. , 80 : 1 – 41 .
   PubMed Web of Science ®Google Scholar
• Yee , S. B. and Pritsos , C. A. 1997 . Comparison of oxygen radical generation from the reductive activation of doxorubicin, streptonigrin, and menadione by xanthine oxidase and xanthine dehydrogenase . Arch. Biochem. Biophys. , 347 ( 2 ) : 235 – 241 .
   PubMed Web of Science ®Google Scholar
• Martin , R. B. 1964 . 2‐amino‐1,4‐naphthoquinone as a model compound for actinomycins . Acta Biochim. Biophys. , 91 : 642 – 644 .
   PubMed Web of Science ®Google Scholar
• Moore , H. W. and Czerniak , R. 1981 . Naturally occurring quinones as potential bioreductive alkylating agents . Med. Res. Rev. , 1 ( 3 ) : 249 – 280 .
   PubMed Web of Science ®Google Scholar
• Papageorgiou , V. P. , Assimopoulou , A. N. , Couladouros , E. A. , Hepworth , D. and Nicolaou , K. C. 1999 . The chemistry and biology of alkannin, shikonin, and related naphthazarin natural products . Angew Chem. Int. Ed. , 38 ( 3 ) : 270 – 301 .
   PubMed Web of Science ®Google Scholar
• Hatzigrigoriou , E. , Papadopoulou , M. V. and Shields , D. 1993 . 2‐Alkylsulfonyloxy‐3‐hydroxy‐1,4‐naphthoquinones: A novel class of radio‐ and chemosensitizers of V79 cells . Oncol. Res. , 5 : 29 – 36 .
   PubMed Web of Science ®Google Scholar
• Asche , C. 2005 . Antitumour quinones . Mini Rev. Med. Chem. , 5 ( 5 ) : 449 – 467 .
   PubMed Web of Science ®Google Scholar
• Inbaraj , J. J. and Chignell , C. F. 2004 . Cytotoxic action of juglone and plumbagin: a mechanistic study using HaCaT keratinocytes . Chem. Res. Toxicol. , 17 : 55 – 62 .
   PubMed Web of Science ®Google Scholar
• Paulsen , M. T. and Ljungman , M. 2005 . The natural toxin juglone causes degradation of p53 and induces rapid H2AX phosphorylation and cell death in human fibroblasts . Toxicol. Appl. Pharmacol. , 209 ( 1 ) : 1 – 9 .
   PubMed Web of Science ®Google Scholar
• Wang , H. , Mao , Y. and Chen , A. Y. 2001 . Stimulation of topoisomerase II‐mediated DNA damage via a mechanism involving protein thiolation . Biochemistry , 40 ( 11 ) : 3316 – 3323 .
   PubMed Web of Science ®Google Scholar
• Chao , S. H. , Greenleaf , A. L. and Price , D. H. 2001 . Juglone, an inhibitor of the peptidyl‐prolyl isomerase Pin1, also directly blocks transcription . Nucleic Acids Res. , 29 : 767 – 773 .
   PubMed Web of Science ®Google Scholar
• Varga , Z. , Bene , L. , Pieri , C. , Damjanovich , S. and Gaspar , R. Jr. 1996 . The effect of juglone on the membrane potential and whole‐cell K+ currents of human lymphocytes . Biochem. Biophys. Res. Commun. , 218 ( 3 ) : 828 – 832 .
   PubMed Web of Science ®Google Scholar
• Habbal , O. A. , Al‐Jabri , A. A. , El‐Hag , A. H. , Al‐Mahrooqi , Z. H. and Al‐Hashmi , N. A. 2005 . In‐vitro antimicrobial activity of Lawsonia inermis Linn (henna). A pilot study on the Omani henna . Saudi Med. J. , 26 ( 1 ) : 69 – 72 .
   PubMed Web of Science ®Google Scholar
• Mikhaeil , B. R. , Badria , F. A. and Maatooq , G. T. 2004 . Antioxidant and immunomodulatory constituents of henna leaves . Z Naturforsch [C]. , 59 ( 7–8 ) : 468 – 476 .
   PubMed Web of Science ®Google Scholar
• Salunke‐Gawali , S. , Rane , S. Y. , Puranik , V. G. , Gugand‐Duhayon , C. and Varret , f . 2004 . Three dimensional hydrogen‐bonding network in a copper complex of 2‐hydroxy‐1,4‐naphthoquinone: Structural, spectroscopic and magnetic properties . Polyhedron , 23 ( 16 ) : 2541 – 2547 .
   Web of Science ®Google Scholar
• Bodini , M. E. , Bravo , P. E. and Aranciba , V. 1994 . Voltammetric and spectroscopic study of the iron(II) complexes with the semiquinone of 2‐hydroxy‐1,4‐naphthoquinone (lawsone) in aprotic medium . Polyhedron , 13 ( 3 ) : 497 – 503 .
   Web of Science ®Google Scholar
• El‐Hendawy , A. M. 1991 . Complexes of lawsone with uranium, molybdenum, ruthenium and osmium, and their use as organic oxidants . Polyhedron , 10 ( 20–21 ) : 2511 – 2518 .
   Web of Science ®Google Scholar
• Garge , P. , Padhye , S. and Tuchagues , J. 1989 . Iron(II) complexes of ortho‐functionalized para‐naphthoquinones 1. Synthesis, characterization, electronic structure and magnetic properties . Inorg. Chim. Acta. , 157 ( 2 ) : 239 – 249 .
   Web of Science ®Google Scholar
• Christianopoulou , M. 1984 . Synthesis and studies of some bivalent metal chelates of 1,2‐dihydroxy‐9,10‐anthracenedione and 5‐hydroxy‐1,4‐naphthalenedione . Polyhedron , 3 ( 6 ) : 7 – 29 .
   Web of Science ®Google Scholar
• Christianopoulou , M. , Ecateriniadou , L. and Sarris , E. 1986 . Evaluation of the antimicrobial activity of a new series of hydroquinone chelates of some transition metals . Eur. J. Med. Chem. , 21 ( 5 ) : 385 – 390 .
   Web of Science ®Google Scholar
• Papageorgiou , V. P. , Christianopoulou , M. , Boutis , L. , Papageorgiou , A. and Tsipis , C. 1986 . Synthesis and antitumor activity of a novel diplatinum complex of the binucleating naphthazarinato ligand . Inorg. Chim. Acta , 124 ( 4 ) : 203 – 206 .
   Web of Science ®Google Scholar
• Bakola‐Christianopoulou , M. , krivos , P. D. , Ecateriniadou , L. B. and Sarris , K. 1988 . On the anti‐bacterial activity of non‐charged μ‐naphthazarinato compounds . Eur. J. Med. Chem. , 23 ( 1 ) : 87 – 90 .
   Web of Science ®Google Scholar
• Lialiaris , T. , Mourelatos , D. , Boutis , L. , Papageorgiou , A. , Christianopoulou , M. , Papageorgiou , V. and Dozi‐Vassiliades , J. 1989 . Comparative study on cytogenetic effects by diplatinum complexes of the ligands of naphthazarine and squaric acid in human lymphocytes . J. Pharmacol. Exp. Therap. , 251 ( 1 ) : 368 – 371 .
   PubMed Web of Science ®Google Scholar
• Gielen , M. , Willem , R. , Biesemans , R. , Boulam , M. , Khloufi , A. and Elde 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 – 291 .
   Web of Science ®Google Scholar
• Gielen , M. 1996 . Tin‐based antitumour drugs . Coord Chem. Rev. , 151 : 41 – 51 .
   Web of Science ®Google Scholar
• 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 . Inorg. Biochem. , 79 : 139 – 145 .
   PubMed Web of Science ®Google Scholar
• Gielen , M. 2002 . Organotin compounds and their therapeutic potential: A report from the organometallic chemistry department of the free university of Brussels . Appl. Organometal. Chem. , 16 : 481 – 494 .
   Web of Science ®Google Scholar
• Gielen , M. , Biesemans , M. and Willem , R. 2005 . Organotin compounds: from kinetics to stereochemistry and antitumour activities . Appl. Organometal. Chem. , 19 : 440 – 450 .
   Web of Science ®Google Scholar
• Pellerito , L. and Nagy , L. 2002 . Organotin(IV)n+ complexes formed with biologically active ligands: equilibrium and structural studies, and some biological aspects . Coord. Chem. Rev. , 224 : 111 – 150 .
   Web of Science ®Google Scholar
• Brown , M.A. , McGarvey , B. R. , Ozarowski , A. and Tuck , D. G. 1998 . Studies of organotin(IV)‐orthoquinone systems . J. Organometal. Chem. , 550 ( 1–2 ) : 165 – 172 .
   Web of Science ®Google Scholar
• 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 – 541 .
   Web of Science ®Google Scholar
• 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. Natl. Cancer Inst. , 82 ( 13 ) : 1107 – 1112 .
   PubMed Web of Science ®Google Scholar
• Marchetti , F. , Pettinari , C. , Cingolani , A. , Pettinari , R. , Rossi , M. and Caruso , F. 2002 . Organotin(IV) derivatives of novel β‐diketones: Part V. Synthesis and characterization of di‐ and triorganotin(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. Organomet. Chem. , 645 ( 1–2 ) : 134 – 145 .
   Web of Science ®Google Scholar
• 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 – 237 .
   Web of Science ®Google Scholar
• Whiffen , D. H. 1956 . Vibrational frequencies and thermodynamic properties of fluoro‐, chloro‐, bromo‐, and iodo‐benzene . J. Chem. Soc. , : 1350 – 1355 .
   Web of Science ®Google Scholar
• Ortiz , A. , Teruel , J. A. and Aranda , F. J. 2005 . Effect of triorganotin compounds on membrane permeability . Biochim. Biophys. Acta. , 1720 ( 1–2 ) : 137 – 142 .
   PubMed Web of Science ®Google Scholar
• Sherman , L. 1988 . Relationship of cytotoxic groups in organotin molecules and the effectiveness of the compounds against leukaemia . Appl. Organometal. Chem. , 2 ( 1 ) : 65 – 72 .
   Google Scholar
• d'Arcy Doherty , M. , Rodgers , A. and Cohen , G. M. 1987 . Mechanisms of toxicity of 2‐ and 5‐hydroxy‐1,4‐naphthoquinone; absence of a role for redox cycling in the toxicity of 2‐hydroxy‐1,4‐naphthoquinone to isolated hepatocytes . J. Appl. Toxicol. , 7 ( 2 ) : 123 – 129 .
   PubMed Web of Science ®Google Scholar
• Babich , A. and Stern , A. 1993 . J. Appl. Toxicol. , 13 ( 5 ) : 353 – 358 . In vitro cytotoxicities of 1,4‐naphthoquinone and hydroxylated 1,4‐naphthoquinones to replicating cells
   PubMed Web of Science ®Google Scholar
• Cooke , G. M. 2002 . Effect of organotins on human aromatase activity in vitro . Toxicol Lett. , 126 ( 2 ) : 121 – 130 .
   PubMed Web of Science ®Google Scholar
• Osada , S. , Nishikawa , J. , Nakanishi , T. , Tanaka , K. and Nishihara , T. 2005 . Some organotin compounds enhance histone acetyltransferase activity . Toxicol. Lett. , 155 ( 2 ) : 329 – 335 .
   PubMed Web of Science ®Google Scholar
• Bolton , J. L. , Pisha , E. , Zhang , F. and Qiu , S. 1998 . Role of quinoids in estrogen carcinogenesis . Chem. Res. Toxicol. , 11 ( 10 ) : 1113 – 1127 .
   PubMed Web of Science ®Google Scholar
• Szorcsik , A. , Nagy , L. and Gajda‐Schrantz , K. 2002 . Structural studies on organotin (IV) complexes formed with ligands containing {S, N, O} donor atoms . J. Radioanal. Nucl. Chem. , 252 ( 3 ) : 523 – 530 .
   Web of Science ®Google Scholar
• Nath , L. M. , Pokharia , S. and Yadav , R. 2001 . Organotin(IV) complexes of amino acids and peptides . Coord. Chem. Rev. , 215 ( 1 ) : 99 – 149 .
   Web of Science ®Google Scholar
• Frisch , M. J. , Trucks , G. W. , Schlegel , H. B. , Scuseria , G. E. , Robb , M. A. , Cheeseman , J. R. , Zakrzewski , V. G. , Montgomery , J. A. , Stratmann , R. E. Jr. , Burant , J. C. , Dapprich , S. , Millam , J. M. , Daniels , A. D. , Kudin , K. N. , Strain , M. C. , Farkas , O. , Tomasi , J. , Barone , V. , Cossi , M. , Cammi , R. , Mennucci , B. , Pomelli , C. , Adamo , C. , Clifford , S. , Ochterski , J. , Petersson , G. A. , Ayala , P. Y. , Cui , Q. , Morokuma , K. , Salvador , P. , Dannenberg , J. J. , Malick , D. K. , Rabuck , A. D. , Raghavachari , K. , Foresman , J. B. , Cioslowski , J. , Ortiz , J. V. , Baboul , A. G. , Stefanov , B. B. , Liu , G. , Liashenko , A. , Piskorz , P. , Komaromi , I. , Gomperts , R. , Martin , R. L. , Fox , D. J. , Keith , T. , Al‐Laham , M. A. , Peng , C. Y. , Nanayakkara , A. , Challacombe , M. , Gill , P. M.W. , Johnson , B. , Chen , W. , Wong , M. W. , Andres , J. L. , Gonzalez , C. , Gordon , M. , Replogle , E. S. and Pople , J. A. 2001 . Pittsburgh, PA : Gaussian Inc. . Gaussian 98 program. Gaussian 98; Revision, A.11
   Google Scholar