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Volumn 15, Issue 5, 2005, Pages 383-391

Alkylating benzamides with melanoma cytotoxicity: Role of melanin, tyrosinase, intracellular pH and DNA interaction

Author keywords

Anticancer drugs; Benzamide conjugates; Chlorambucil; Chloroquine; Dacarbazine; DNA binding; Melanin binding; Melanosomal pH; Phenylisothiourea; Targeted melanoma therapy; Tyrosinase

Indexed keywords

BENZAMIDE DERIVATIVE; CHLORAMBUCIL; CHLOROQUINE; CYTOSTATIC AGENT; DACARBAZINE; DNA; DRUG CARRIER; MELANIN; MONOPHENOL MONOOXYGENASE; PHENYLISOTHIOUREA; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

EID: 27644518128     PISSN: 09608931     EISSN: None     Source Type: Journal    
DOI: 10.1097/00008390-200510000-00006     Document Type: Article
Times cited : (15)

References (28)
  • 1
    • 0347503603 scopus 로고    scopus 로고
    • Palliative therapy of disseminated malignant melanoma: A systematic review of 41 randomised clinical trials
    • Eigentler TK, Caroli UM, Radny P, Garbe C. Palliative therapy of disseminated malignant melanoma: a systematic review of 41 randomised clinical trials. Lancet Oncol 2003; 4:748-759.
    • (2003) Lancet Oncol , vol.4 , pp. 748-759
    • Eigentler, T.K.1    Caroli, U.M.2    Radny, P.3    Garbe, C.4
  • 2
    • 0034936580 scopus 로고    scopus 로고
    • Melanocyte-directed enzyme prodrug therapy (MDEPT) - Development of second generation prodrugs for targeted treatment of malignant melanoma
    • Jordan AM, Khan TH, Malkin H, Osborn HM, Photiou A, Riley PA. Melanocyte-directed enzyme prodrug therapy (MDEPT) - development of second generation prodrugs for targeted treatment of malignant melanoma. Bioorg Med Chem 2001; 9:1549-1558.
    • (2001) Bioorg Med Chem , vol.9 , pp. 1549-1558
    • Jordan, A.M.1    Khan, T.H.2    Malkin, H.3    Osborn, H.M.4    Photiou, A.5    Riley, P.A.6
  • 3
    • 0028998282 scopus 로고
    • Antimelanoma effect of 4-S-cysteaminylcatechol - An activated form of 4-S-cysteaminylphenol
    • Inoue S, Hasegawa K, Ito S, Ozeki H, Solano F, Jimenez-Cervantes C, et al. Antimelanoma effect of 4-S-cysteaminylcatechol - an activated form of 4-S-cysteaminylphenol. Cancer Res 1995; 55:2603-2607.
    • (1995) Cancer Res , vol.55 , pp. 2603-2607
    • Inoue, S.1    Hasegawa, K.2    Ito, S.3    Ozeki, H.4    Solano, F.5    Jimenez-Cervantes, C.6
  • 4
    • 0043193607 scopus 로고
    • In vitro studies of 2,4-dihydroxyphenylalanine, a prodrug targeted against malignant melanoma cells
    • Morrison ME, Yagi MJ, Cohen G. In vitro studies of 2,4- dihydroxyphenylalanine, a prodrug targeted against malignant melanoma cells. Proc Natl Acad Sci USA 1985; 82:2960-2964.
    • (1985) Proc Natl Acad Sci USA , vol.82 , pp. 2960-2964
    • Morrison, M.E.1    Yagi, M.J.2    Cohen, G.3
  • 5
    • 0032560235 scopus 로고    scopus 로고
    • Therapeutic effects of monoclonal antibody-beta-lactamase conjugates in combination with a nitrogen mustard anticancer prodrug in models of human renal cell carcinoma
    • Svensson HP, Frank IS, Berry KK, Senter PD. Therapeutic effects of monoclonal antibody-beta-lactamase conjugates in combination with a nitrogen mustard anticancer prodrug in models of human renal cell carcinoma. J Med Chem 1998; 41:1507-1512.
    • (1998) J Med Chem , vol.41 , pp. 1507-1512
    • Svensson, H.P.1    Frank, I.S.2    Berry, K.K.3    Senter, P.D.4
  • 6
    • 0032808621 scopus 로고    scopus 로고
    • Comparative cytotoxicity and pharmacokinetics of antimelanoma immunotoxins containing either natural or recombinant gelonin
    • Rosenblum MG, Marks JW, Cheung LH. Comparative cytotoxicity and pharmacokinetics of antimelanoma immunotoxins containing either natural or recombinant gelonin. Cancer Chemother Pharmacol 1999; 44:343-348.
    • (1999) Cancer Chemother Pharmacol , vol.44 , pp. 343-348
    • Rosenblum, M.G.1    Marks, J.W.2    Cheung, L.H.3
  • 7
    • 0033230497 scopus 로고    scopus 로고
    • Comparison of recombinant and synthetically formed monoclonal antibody-beta-lactamase conjugates for anticancer prodrug activation
    • Kerr DE, Vrudhula VM, Svensson HP, Siemers NO, Senter PD. Comparison of recombinant and synthetically formed monoclonal antibody-beta-lactamase conjugates for anticancer prodrug activation. Bioconjug Chem 1999; 10:1084-1089.
    • (1999) Bioconjug Chem , vol.10 , pp. 1084-1089
    • Kerr, D.E.1    Vrudhula, V.M.2    Svensson, H.P.3    Siemers, N.O.4    Senter, P.D.5
  • 8
    • 0028177662 scopus 로고
    • Receptor mediated cytotoxicity of α-MSH fragments containing melphalan in a human melanoma cell line
    • Morandini R, Suli-Vargha H, Libert A, Loir B, Botyanszki J, Medzihradszky K, et al. Receptor mediated cytotoxicity of α-MSH fragments containing melphalan in a human melanoma cell line. Int J Cancer 1994; 56:129-133.
    • (1994) Int J Cancer , vol.56 , pp. 129-133
    • Morandini, R.1    Suli-Vargha, H.2    Libert, A.3    Loir, B.4    Botyanszki, J.5    Medzihradszky, K.6
  • 10
    • 0027317379 scopus 로고
    • Phase II scintigraphic clinical trial of malignant melanoma with iodine-123-N-(2-diethylaminoethyl-4-iodobenzamide)
    • Michelot JM, Moreau MCF, Veyre AJ, Bonafous JF, Bacin FJ, Madelmont JC, et al. Phase II scintigraphic clinical trial of malignant melanoma with iodine-123-N-(2-diethylaminoethyl-4-iodobenzamide). J Nucl Med 1993; 34:1260-1266.
    • (1993) J Nucl Med , vol.34 , pp. 1260-1266
    • Michelot, J.M.1    Moreau, M.C.F.2    Veyre, A.J.3    Bonafous, J.F.4    Bacin, F.J.5    Madelmont, J.C.6
  • 12
    • 0034687239 scopus 로고    scopus 로고
    • Radioiodinated N-(2-diethylaminoethyl)benzamide derivatives with high melanoma uptake - Structure-affinity relationships, metabolic fate, and intracellular localization
    • Eisenhut M, Hull WE, Mohammed A, Mier W, Lay D, Just W, et al. Radioiodinated N-(2-diethylaminoethyl)benzamide derivatives with high melanoma uptake - structure-affinity relationships, metabolic fate, and intracellular localization. J Med Chem 2000; 43:3913-3922.
    • (2000) J Med Chem , vol.43 , pp. 3913-3922
    • Eisenhut, M.1    Hull, W.E.2    Mohammed, A.3    Mier, W.4    Lay, D.5    Just, W.6
  • 14
    • 0037648966 scopus 로고    scopus 로고
    • Transcription factors as targets for DNA-interacting drugs
    • Gniazdowski M, Denny WA, Nelson SM, Czyz M. Transcription factors as targets for DNA-interacting drugs. Curr Med Chem 2003; 10:909-924.
    • (2003) Curr Med Chem , vol.10 , pp. 909-924
    • Gniazdowski, M.1    Denny, W.A.2    Nelson, S.M.3    Czyz, M.4
  • 15
    • 0035425773 scopus 로고    scopus 로고
    • Melanosomal pH controls rate of melanogenesis, eumelanin/phaeomelanin ratio and melanosome maturation in melanocytes and melanoma cells
    • Ancans J, Tobin DJ, Hoogduijn MJ, Smit NP, Wakamatsu K, Thody AJ. Melanosomal pH controls rate of melanogenesis, eumelanin/phaeomelanin ratio and melanosome maturation in melanocytes and melanoma cells. Exp Cell Res 2001; 268:26-35.
    • (2001) Exp Cell Res , vol.268 , pp. 26-35
    • Ancans, J.1    Tobin, D.J.2    Hoogduijn, M.J.3    Smit, N.P.4    Wakamatsu, K.5    Thody, A.J.6
  • 16
    • 0027365449 scopus 로고
    • pH of melanosomes of B16 murine melanoma is acidic: Its physiological importance in the regulation of melanin biosynthesis
    • Bhatnagar V, Anjaiah S, Puri N, Darshanam BN, Ramaiah A. pH of melanosomes of B16 murine melanoma is acidic: its physiological importance in the regulation of melanin biosynthesis. Arch Biochem Biophys 1993; 307:183-192.
    • (1993) Arch Biochem Biophys , vol.307 , pp. 183-192
    • Bhatnagar, V.1    Anjaiah, S.2    Puri, N.3    Darshanam, B.N.4    Ramaiah, A.5
  • 17
    • 0034726055 scopus 로고    scopus 로고
    • Activation of melanogenesis by vacuolar type H(+)-ATPase inhibitors in amelanotic, tyrosinase positive human and mouse melanoma cells
    • Ancans J, Thody AJ. Activation of melanogenesis by vacuolar type H(+)-ATPase inhibitors in amelanotic, tyrosinase positive human and mouse melanoma cells. FEBS Lett 2000; 478:57-60.
    • (2000) FEBS Lett , vol.478 , pp. 57-60
    • Ancans, J.1    Thody, A.J.2
  • 18
    • 0034214275 scopus 로고    scopus 로고
    • Rapid and sensitive ethidium bromide fluorescence quenching assay of polyamine conjugate-DNA interactions for the analysis of lipoplex formation in gene therapy
    • Geall JG, Blagbrough IS. Rapid and sensitive ethidium bromide fluorescence quenching assay of polyamine conjugate-DNA interactions for the analysis of lipoplex formation in gene therapy. J Pharm Biomed Anal 2000; 22:849-859.
    • (2000) J Pharm Biomed Anal , vol.22 , pp. 849-859
    • Geall, J.G.1    Blagbrough, I.S.2
  • 19
    • 0037139384 scopus 로고    scopus 로고
    • Binding of doxycycline to keratin, melanin and human epidermal tissue
    • Banning TP, Heard CM. Binding of doxycycline to keratin, melanin and human epidermal tissue. Int J Pharm 2002; 20:219-227.
    • (2002) Int J Pharm , vol.20 , pp. 219-227
    • Banning, T.P.1    Heard, C.M.2
  • 20
    • 0042196266 scopus 로고    scopus 로고
    • Melanin inhibits cytotoxic effects of doxorubicin and daunorubicin in MOLT 4 cells
    • Svensson SPS, Lindgren S, Powell W, Green H. Melanin inhibits cytotoxic effects of doxorubicin and daunorubicin in MOLT 4 cells. Pigment Cell Res 2003; 16:351-354.
    • (2003) Pigment Cell Res , vol.16 , pp. 351-354
    • Svensson, S.P.S.1    Lindgren, S.2    Powell, W.3    Green, H.4
  • 21
    • 0024632148 scopus 로고
    • L-tyrosine, L-dopa, and tyrosinase as positive regulators of the subcellular apparatus of melanogenesis in Bomirski Ab amelanotic melanoma cells
    • Slominski A, Moellmann G, Kuklinska E. L-tyrosine, L-dopa, and tyrosinase as positive regulators of the subcellular apparatus of melanogenesis in Bomirski Ab amelanotic melanoma cells. Pigment Cell Res 1989; 2:109-116.
    • (1989) Pigment Cell Res , vol.2 , pp. 109-116
    • Slominski, A.1    Moellmann, G.2    Kuklinska, E.3
  • 22
    • 0036068103 scopus 로고    scopus 로고
    • The effect of niacinamide on reducing cutaneous pigmentation and suppression of melanosome transfer
    • Hakozaki T, Minwalla L, Zhuang J, Chhoa M, Matsubara A, Miyamoto K, et al. The effect of niacinamide on reducing cutaneous pigmentation and suppression of melanosome transfer. Br J Dermatol 2002; 147:20-31.
    • (2002) Br J Dermatol , vol.147 , pp. 20-31
    • Hakozaki, T.1    Minwalla, L.2    Zhuang, J.3    Chhoa, M.4    Matsubara, A.5    Miyamoto, K.6
  • 23
    • 0035862188 scopus 로고    scopus 로고
    • Regulation of the catalytic activity of preexisting tyrosinase in black and Caucasian human melanocyte cell cultures
    • Fuller BB, Spaulding DT, Smith DR. Regulation of the catalytic activity of preexisting tyrosinase in black and Caucasian human melanocyte cell cultures. Exp Cell Res 2001; 262:197-208.
    • (2001) Exp Cell Res , vol.262 , pp. 197-208
    • Fuller, B.B.1    Spaulding, D.T.2    Smith, D.R.3
  • 24
    • 0032086720 scopus 로고    scopus 로고
    • Human melanoma cell lines show little relationship between expression of pigmentation genes and pigmentary behaviour in vitro
    • Eberle J, Wagner M, MacNeil S. Human melanoma cell lines show little relationship between expression of pigmentation genes and pigmentary behaviour in vitro. Pigment Cell Res 1998; 11:134-142.
    • (1998) Pigment Cell Res , vol.11 , pp. 134-142
    • Eberle, J.1    Wagner, M.2    MacNeil, S.3
  • 26
    • 7144229386 scopus 로고    scopus 로고
    • Chemotherapeutic drug-induced apoptosis in human leukaemic cells is independent of the Fas (APO-1/CD95) receptor/ligand system
    • McGahon AJ, Costa Pereira AP, Cotter LD, Cotter TG. Chemotherapeutic drug-induced apoptosis in human leukaemic cells is independent of the Fas (APO-1/CD95) receptor/ligand system. Br J Haematol 1998; 101:539.
    • (1998) Br J Haematol , vol.101 , pp. 539
    • McGahon, A.J.1    Costa Pereira, A.P.2    Cotter, L.D.3    Cotter, T.G.4
  • 27
    • 0022416873 scopus 로고
    • An electrometric method for the determination of tyrosinase activity
    • Solano-Munoz F, Penafiel R, Galindo JD. An electrometric method for the determination of tyrosinase activity. Biochem J 1985; 229:573-578.
    • (1985) Biochem J , vol.229 , pp. 573-578
    • Solano-Munoz, F.1    Penafiel, R.2    Galindo, J.D.3
  • 28
    • 0035678873 scopus 로고    scopus 로고
    • Role of cytochrome P450 isoenzymes in metabolism of O(6)-benzylguanine: Implications for dacarbazine activation
    • Long L, Dolan ME. Role of cytochrome P450 isoenzymes in metabolism of O(6)-benzylguanine: implications for dacarbazine activation. Clin Cancer Res 2001; 7:4239-4244.
    • (2001) Clin Cancer Res , vol.7 , pp. 4239-4244
    • Long, L.1    Dolan, M.E.2


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