메뉴 건너뛰기




Volumn 36, Issue 10, 2006, Pages 765-775

Synthesis, structure and in vitro biological activity of new hydroxy-naphthoquinonato triorganotin compounds

Author keywords

Hydroxy naphthoquinones; SRB assay; Triorganotins

Indexed keywords


EID: 33845286554     PISSN: 15533174     EISSN: 15533182     Source Type: Journal    
DOI: 10.1080/15533170601028298     Document Type: Article
Times cited : (8)

References (45)
  • 1
    • 0026040838 scopus 로고
    • Molecular mechanisms of quinone cytotoxicity
    • O'Brien, P. J. Molecular mechanisms of quinone cytotoxicity. Chem. Biol. Interact. 1991, 80, 1-41.
    • (1991) Chem. Biol. Interact. , vol.80 , pp. 1-41
    • O'Brien, P.J.1
  • 2
    • 0031573471 scopus 로고    scopus 로고
    • Comparison of oxygen radical generation from the reductive activation of doxorubicin, streptonigrin, and menadione by xanthine oxidase and xanthine dehydrogenase
    • Yee, S. B.; Pritsos, C. A. Comparison of oxygen radical generation from the reductive activation of doxorubicin, streptonigrin, and menadione by xanthine oxidase and xanthine dehydrogenase. Arch. Biochem. Biophys. 1997, 347(2), 235-241.
    • (1997) Arch. Biochem. Biophys. , vol.347 , Issue.2 , pp. 235-241
    • Yee, S.B.1    Pritsos, C.A.2
  • 3
    • 33845297494 scopus 로고
    • 2-Amino-1,4-naphthoquinone as a model compound for actinomycins
    • Martin, R. B. 2-amino-1,4-naphthoquinone as a model compound for actinomycins. Acta Biochim. Biophys, 1964, 91, 642-644.
    • (1964) Acta Biochim. Biophys , vol.91 , pp. 642-644
    • Martin, R.B.1
  • 4
    • 0019724691 scopus 로고
    • Naturally occurring quinones as potential bioreductive alkylating agents
    • Moore, H. W.; Czerniak, R. Naturally occurring quinones as potential bioreductive alkylating agents. Med. Res. Rev. 1981, 1 (3), 249-280.
    • (1981) Med. Res. Rev. , vol.1 , Issue.3 , pp. 249-280
    • Moore, H.W.1    Czerniak, R.2
  • 6
    • 0027245940 scopus 로고
    • 2-Alkylsulfonyloxy-3-hydroxy-1,4-naphthoquinones: A novel class of radio- And chemosensitizers of V79 cells
    • Hatzigrigoriou, E.; Papadopoulou, M. V; Shields, D. 2-Alkylsulfonyloxy-3- hydroxy-1,4-naphthoquinones: A novel class of radio- and chemosensitizers of V79 cells. Oncol. Res. 1993, 5, 29-36.
    • (1993) Oncol. Res. , vol.5 , pp. 29-36
    • Hatzigrigoriou, E.1    Papadopoulou, M.V.2    Shields, D.3
  • 7
    • 18044375989 scopus 로고    scopus 로고
    • Antitumour quinones
    • Asche, C. Antitumour quinones. Mini Rev. Med. Chem. 2005, 5 (5), 449-467.
    • (2005) Mini Rev. Med. Chem. , vol.5 , Issue.5 , pp. 449-467
    • Asche, C.1
  • 8
    • 1642498276 scopus 로고    scopus 로고
    • Cytotoxic action of juglone and plumbagin: A mechanistic study using HaCaT keratinocytes
    • Inbaraj, J. J.; Chignell, C. F. Cytotoxic action of juglone and plumbagin: a mechanistic study using HaCaT keratinocytes. Chem. Res. Toxicol. 2004, 17, 55-62.
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 55-62
    • Inbaraj, J.J.1    Chignell, C.F.2
  • 9
    • 27544443196 scopus 로고    scopus 로고
    • The natural toxin juglone causes degradation of p53 and induces rapid H2AX phosphorylation and cell death in human fibroblasts
    • Paulsen, M. T; Ljungman, M. The natural toxin juglone causes degradation of p53 and induces rapid H2AX phosphorylation and cell death in human fibroblasts. Toxicol. Appl. Pharmacol. 2005, 209 (1), 1-9.
    • (2005) Toxicol. Appl. Pharmacol. , vol.209 , Issue.1 , pp. 1-9
    • Paulsen, M.T.1    Ljungman, M.2
  • 10
    • 0035916938 scopus 로고    scopus 로고
    • Stimulation of topoisomerase II-mediated DNA damage via a mechanism involving protein thiolation
    • Wang, H.; Mao, Y.; Chen, A. Y. Stimulation of topoisomerase II-mediated DNA damage via a mechanism involving protein thiolation. Biochemistry 2001, 40 (11), 3316-3323.
    • (2001) Biochemistry , vol.40 , Issue.11 , pp. 3316-3323
    • Wang, H.1    Mao, Y.2    Chen, A.Y.3
  • 11
    • 0035253619 scopus 로고    scopus 로고
    • Juglone, an inhibitor of the peptidyl-prolyl isomerase Pin 1, also directly blocks transcription
    • Chao, S. H.; Greenleaf, A. L.; Price, D. H. Juglone, an inhibitor of the peptidyl-prolyl isomerase Pin 1, also directly blocks transcription. Nucleic Acids Res. 2001, 29, 767-773.
    • (2001) Nucleic Acids Res. , vol.29 , pp. 767-773
    • Chao, S.H.1    Greenleaf, A.L.2    Price, D.H.3
  • 12
    • 0030050898 scopus 로고    scopus 로고
    • The effect of juglone on the membrane potential and whole-cell K+ currents of human lymphocytes
    • Varga, Z.; Bene, L.; Pieri, C.; Damjanovich, S.; Gaspar, R. Jr. The effect of juglone on the membrane potential and whole-cell K+ currents of human lymphocytes. Biochem. Biophys. Res. Commun. 1996, 218 (3), 828-832.
    • (1996) Biochem. Biophys. Res. Commun. , vol.218 , Issue.3 , pp. 828-832
    • Varga, Z.1    Bene, L.2    Pieri, C.3    Damjanovich, S.4    Gaspar Jr., R.5
  • 13
    • 14944364646 scopus 로고    scopus 로고
    • In-vitro antimicrobial activity of Lawsonia inermis Linn (henna). A pilot study on the Omani henna
    • Habbal, O. A.; Al-Jabri, A. A.; El-Hag, A.H.; Al-Mahrooqi, Z. H.; Al-Hashmi, N. A. In-vitro antimicrobial activity of Lawsonia inermis Linn (henna). A pilot study on the Omani henna. Saudi Med. J. 2005, 26 (1), 69-72.
    • (2005) Saudi Med. J. , vol.26 , Issue.1 , pp. 69-72
    • Habbal, O.A.1    Al-Jabri, A.A.2    El-Hag, A.H.3    Al-Mahrooqi, Z.H.4    Al-Hashmi, N.A.5
  • 14
    • 4143066900 scopus 로고    scopus 로고
    • Antioxidant and immunomodulatory constituents of henna leaves
    • Mikhaeil, B. R.; Badria, F. A.; Maatooq, G. T. Antioxidant and immunomodulatory constituents of henna leaves. Z Naturforsch [C]. 2004, 59 (7-8), 468-476.
    • (2004) Z Naturforsch [C] , vol.59 , Issue.7-8 , pp. 468-476
    • Mikhaeil, B.R.1    Badria, F.A.2    Maatooq, G.T.3
  • 15
    • 14544296670 scopus 로고    scopus 로고
    • Three dimensional hydrogen-bonding network in a copper complex of 2-hydroxy-1,4-naphthoquinone: Structural, spectroscopic and magnetic properties
    • Salunke-Gawali, S.; Rane, S. Y.; Puranik, V. G; Gugand-Duhayon, C.; Varret, f. Three dimensional hydrogen-bonding network in a copper complex of 2-hydroxy-1,4-naphthoquinone: Structural, spectroscopic and magnetic properties. Polyhedron 2004, 25(16), 2541-2547.
    • (2004) Polyhedron , vol.25 , Issue.16 , pp. 2541-2547
    • Salunke-Gawali, S.1    Rane, S.Y.2    Puranik, V.G.3    Gugand-Duhayon, C.4    Varret, F.5
  • 16
    • 0000239574 scopus 로고
    • Voltammetric and spectroscopic study of the iron(II) complexes with the semiquinone of 2-hydroxy-1,4-naphthoquinone (lawsone) in aprotic medium
    • Bodini, M. E.; Bravo, P. E.; Aranciba, V. Voltammetric and spectroscopic study of the iron(II) complexes with the semiquinone of 2-hydroxy-1,4- naphthoquinone (lawsone) in aprotic medium. Polyhedron 1994, 13 (3), 497-503.
    • (1994) Polyhedron , vol.13 , Issue.3 , pp. 497-503
    • Bodini, M.E.1    Bravo, P.E.2    Aranciba, V.3
  • 17
    • 0002725167 scopus 로고
    • Complexes of lawsone with uranium, molybdenum, ruthenium and osmium, and their use as organic oxidants
    • El-Hendawy, A. M. Complexes of lawsone with uranium, molybdenum, ruthenium and osmium, and their use as organic oxidants. Polyhedron 1991, 10 (20-21), 2511-2518.
    • (1991) Polyhedron , vol.10 , Issue.20-21 , pp. 2511-2518
    • El-Hendawy, A.M.1
  • 18
    • 0038917836 scopus 로고
    • Iron(II) complexes of ortho-functionalized para-naphthoquinones 1. Synthesis, characterization, electronic structure and magnetic properties
    • Garge, P.; Padhye, S.; Tuchagues, J. Iron(II) complexes of ortho-functionalized para-naphthoquinones 1. Synthesis, characterization, electronic structure and magnetic properties. Inorg. Chim. Acta. 1989, 157 (2), 239-249.
    • (1989) Inorg. Chim. Acta. , vol.157 , Issue.2 , pp. 239-249
    • Garge, P.1    Padhye, S.2    Tuchagues, J.3
  • 19
    • 33845325963 scopus 로고
    • Synthesis and studies of some bivalent metal chelates of 1,2-dihydroxy-9,10-anthracenedione and 5-hydroxy-1,4-naphthalenedione
    • Christianopoulou, M. Synthesis and studies of some bivalent metal chelates of 1,2-dihydroxy-9,10-anthracenedione and 5-hydroxy-1,4- naphthalenedione. Polyhedron 1984, 3 (6), 7-29.
    • (1984) Polyhedron , vol.3 , Issue.6 , pp. 7-29
    • Christianopoulou, M.1
  • 20
    • 0022973246 scopus 로고
    • Evaluation of the antimicrobial activity of a new series of hydroquinone chelates of some transition metals
    • Christianopoulou, M.; Ecateriniadou, L.; Sarris, E. Evaluation of the antimicrobial activity of a new series of hydroquinone chelates of some transition metals. Eur. J. Med. Chem. 1986, 21 (5), 385-390.
    • (1986) Eur. J. Med. Chem. , vol.21 , Issue.5 , pp. 385-390
    • Christianopoulou, M.1    Ecateriniadou, L.2    Sarris, E.3
  • 21
    • 0344676487 scopus 로고
    • Synthesis and antitumor activity of a novel diplatinum complex of the binucleating naphthazarinato ligand
    • Papageorgiou, V. P.; Christianopoulou, M.; Boutis, L.; Papageorgiou, A.; Tsipis, C. Synthesis and antitumor activity of a novel diplatinum complex of the binucleating naphthazarinato ligand. Inorg. Chim. Acta 1986, 124 (4), 203-206.
    • (1986) Inorg. Chim. Acta , vol.124 , Issue.4 , pp. 203-206
    • Papageorgiou, V.P.1    Christianopoulou, M.2    Boutis, L.3    Papageorgiou, A.4    Tsipis, C.5
  • 24
    • 84990504326 scopus 로고
    • Exceptionally high in vitro antitumor activity of substituted triphenyltin benzoates including salicylates against a human mammary tumor, MCF-7, and a colon carcinoma, WiDr
    • Gielen, M.; Willem, R.; Biesemans, R.; Boulam, M.; Khloufi, A.; Elde Vos, D. 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. 1992, 6 (3), 287-291.
    • (1992) Appl. Organometal. Chem. , vol.6 , Issue.3 , pp. 287-291
    • Gielen, M.1    Willem, R.2    Biesemans, R.3    Boulam, M.4    Khloufi, A.5    Elde Vos, D.6
  • 25
    • 0030545818 scopus 로고    scopus 로고
    • Tin-based antitumour drugs
    • Gielen, M. Tin-based antitumour drugs. Coord Chem. Rev. 1996, 151, 41-51.
    • (1996) Coord Chem. Rev. , vol.151 , pp. 41-51
    • Gielen, M.1
  • 26
    • 0034732642 scopus 로고    scopus 로고
    • Synthesis, characterization and in vitro antitumor activity of di- And triorganotin derivatives of polyoxa- and biologically relevant carboxylic acids
    • Gielen, M.; Biesemans, M.; de Vos, D.; Willem, R. Synthesis, characterization and in vitro antitumor activity of di- and triorganotin derivatives of polyoxa- and biologically relevant carboxylic acids. Inorg. Biochem. 2000, 79, 139-145.
    • (2000) Inorg. Biochem. , vol.79 , pp. 139-145
    • Gielen, M.1    Biesemans, M.2    De Vos, D.3    Willem, R.4
  • 27
    • 0036054279 scopus 로고    scopus 로고
    • Organotin compounds and their therapeutic potential: A report from the organometallic chemistry department of the free university of Brussels
    • Gielen, M. Organotin compounds and their therapeutic potential: A report from the organometallic chemistry department of the free university of Brussels. Appl. Organometal. Chem. 2002, 16, 481-494.
    • (2002) Appl. Organometal. Chem. , vol.16 , pp. 481-494
    • Gielen, M.1
  • 28
    • 16344379389 scopus 로고    scopus 로고
    • Organotin compounds: From kinetics to stereochemistry and antitumour activities
    • Gielen, M.; Biesemans, M.; Willem, R. Organotin compounds: from kinetics to stereochemistry and antitumour activities. Appl. Organometal. Chem. 2005, 19, 440-450.
    • (2005) Appl. Organometal. Chem. , vol.19 , pp. 440-450
    • Gielen, M.1    Biesemans, M.2    Willem, R.3
  • 29
    • 0036159969 scopus 로고    scopus 로고
    • Organotin(IV)n+ complexes formed with biologically active ligands: Equilibrium and structural studies, and some biological aspects
    • Pellerito, L.; Nagy, L. Organotin(IV)n+ complexes formed with biologically active ligands: equilibrium and structural studies, and some biological aspects. Coord. Chem. Rev. 2002, 224, 111-150.
    • (2002) Coord. Chem. Rev. , vol.224 , pp. 111-150
    • Pellerito, L.1    Nagy, L.2
  • 31
    • 33947480660 scopus 로고
    • Direct synthesis of organtotin compounds. I. Di and tri-benzyltin chlorides
    • Sisido, K.; Takeda, Y.; Kinugawa, Z. Direct synthesis of organtotin compounds. I. Di and tri-benzyltin chlorides. J. Am. Chem. Soc. 1960, 83, 538-541.
    • (1960) J. Am. Chem. Soc. , vol.83 , pp. 538-541
    • Sisido, K.1    Takeda, Y.2    Kinugawa, Z.3
  • 33
    • 0036158982 scopus 로고    scopus 로고
    • 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)
    • Marchetti, F.; Pettinari, C.; Cingolani, A.; Pettinari, R.; Rossi, M.; Caruso, F. 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. 2002, 645 (1-2), 134-145.
    • (2002) J. Organomet. Chem. , vol.645 , Issue.1-2 , pp. 134-145
    • Marchetti, F.1    Pettinari, C.2    Cingolani, A.3    Pettinari, R.4    Rossi, M.5    Caruso, F.6
  • 35
    • 0003154945 scopus 로고
    • Vibrational frequencies and thermodynamic properties of fluoro-, chloro-, bromo-, and iodo-benzene
    • Whiffen, D. H. Vibrational frequencies and thermodynamic properties of fluoro-, chloro-, bromo-, and iodo-benzene. J. Chem. Soc. 1956, 1350-1355.
    • (1956) J. Chem. Soc. , pp. 1350-1355
    • Whiffen, D.H.1
  • 36
    • 32144447978 scopus 로고    scopus 로고
    • Effect of triorganotin compounds on membrane permeability
    • Ortiz, A.; Teruel, J. A.; Aranda, F. J. Effect of triorganotin compounds on membrane permeability. Biochim. Biophys. Acta. 2005, 1720 (1-2), 137-142.
    • (2005) Biochim. Biophys. Acta. , vol.1720 , Issue.1-2 , pp. 137-142
    • Ortiz, A.1    Teruel, J.A.2    Aranda, F.J.3
  • 37
    • 84990551140 scopus 로고
    • Relationship of cytotoxic groups in organotin molecules and the effectiveness of the compounds against leukaemia
    • Sherman, L. Relationship of cytotoxic groups in organotin molecules and the effectiveness of the compounds against leukaemia. Appl. Organometal. Chem. 1988, 2 (1), 65-72.
    • (1988) Appl. Organometal. Chem. , vol.2 , Issue.1 , pp. 65-72
    • Sherman, L.1
  • 38
    • 0023641132 scopus 로고
    • 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
    • d'Arcy Doherty, M.; Rodgers, A.; Cohen, G. M. 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. 1987, 7 (2), 123-129.
    • (1987) J. Appl. Toxicol. , vol.7 , Issue.2 , pp. 123-129
    • D'Arcy Doherty, M.1    Rodgers, A.2    Cohen, G.M.3
  • 39
    • 0027441799 scopus 로고
    • In vitro cytotoxicities of 1,4-naphthoquinone and hydroxylated 1,4-naphthoquinones to replicating cells
    • Babich, A.; Stern, A. In vitro cytotoxicities of 1,4-naphthoquinone and hydroxylated 1,4-naphthoquinones to replicating cells. J. Appl. Toxicol. 1993, 13(5), 353-358.
    • (1993) J. Appl. Toxicol. , vol.13 , Issue.5 , pp. 353-358
    • Babich, A.1    Stern, A.2
  • 40
    • 0037168962 scopus 로고    scopus 로고
    • Effect of organotins on human aromatase activity in vitro
    • Cooke, G. M. Effect of organotins on human aromatase activity in vitro. Toxicol Lett. 2002, 126 (2), 121-130.
    • (2002) Toxicol Lett. , vol.126 , Issue.2 , pp. 121-130
    • Cooke, G.M.1
  • 41
    • 10444251007 scopus 로고    scopus 로고
    • Some organotin compounds enhance histone acetyltransferase activity
    • Osada, S.; Nishikawa, J.; Nakanishi, T.; Tanaka, K.; Nishihara, T. Some organotin compounds enhance histone acetyltransferase activity. Toxicol. Lett. 2005, 155 (2), 329-335.
    • (2005) Toxicol. Lett. , vol.155 , Issue.2 , pp. 329-335
    • Osada, S.1    Nishikawa, J.2    Nakanishi, T.3    Tanaka, K.4    Nishihara, T.5
  • 42
    • 0031741669 scopus 로고    scopus 로고
    • Role of quinoids in estrogen carcinogenesis
    • Bolton, J. L.; Pisha, E.; Zhang, F.; Qiu, S. Role of quinoids in estrogen carcinogenesis. Chem. Res. Toxicol. 1998, 11 (10), 1113-1127.
    • (1998) Chem. Res. Toxicol. , vol.11 , Issue.10 , pp. 1113-1127
    • Bolton, J.L.1    Pisha, E.2    Zhang, F.3    Qiu, S.4
  • 43
    • 0036335105 scopus 로고    scopus 로고
    • Structural studies on organotin (IV) complexes formed with ligands containing {S, N, O} donor atoms
    • Szorcsik, A.; Nagy, L.; Gajda-Schrantz, K. Structural studies on organotin (IV) complexes formed with ligands containing {S, N, O} donor atoms. J. Radioanal. Nucl. Chem. 2002, 252 (3), 523-530.
    • (2002) J. Radioanal. Nucl. Chem. , vol.252 , Issue.3 , pp. 523-530
    • Szorcsik, A.1    Nagy, L.2    Gajda-Schrantz, K.3
  • 44
    • 0035023902 scopus 로고    scopus 로고
    • Organotin(IV) complexes of amino acids and peptides
    • Nath, L. M.; Pokharia, S.; Yadav, R. Organotin(IV) complexes of amino acids and peptides. Coord. Chem. Rev. 2001, 215 (1), 99-149.
    • (2001) Coord. Chem. Rev. , vol.215 , Issue.1 , pp. 99-149
    • Nath, L.M.1    Pokharia, S.2    Yadav, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.