메뉴 건너뛰기




Volumn 26, Issue 1, 2013, Pages 151-165

Gallium(III) complexes with 2-acetylpyridine-derived thiosemicarbazones: Antimicrobial and cytotoxic effects and investigation on the interactions with tubulin

Author keywords

Antimicrobial activity; Cytotoxicity; Gallium(III) complexes; Thiosemicarbazones; Tubulin

Indexed keywords

2 ACETYLPYRIDINE THIOSEMICARBAZONE; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; BIS[N 4 CHLOROPHENYL 2 ACETYLPYRIDINETHIOSEMICARBAZONATO]GALLIUM (III)NITRATE; BIS[N 4 FLUOROPHENYL 2 ACETYLPYRIDINETHIOSEMICARBAZONATO]GALLIUM (III)NITRATE; BIS[N 4 IODOPHENYL 2 ACETYLPYRIDINETHIOSEMICARBAZONATO]GALLIUM (III)NITRATE; BIS[N 4 NITROPHENYL 2 ACETYLPYRIDINETHIOSEMICARBAZONATO]GALLIUM (III)NITRATE TRIHYDRATE; BIS[N PARA TOLYL 2 ACETYLPYRIDINETHIOSEMICARBAZONATO]GALLIUM (III)NITRATE; ETOPOSIDE; FLUCONAZOLE; GALLIUM; TETRACYCLINE; TUBULIN; UNCLASSIFIED DRUG;

EID: 84873410373     PISSN: 09660844     EISSN: 15728773     Source Type: Journal    
DOI: 10.1007/s10534-012-9603-1     Document Type: Article
Times cited : (42)

References (48)
  • 1
    • 0037173568 scopus 로고    scopus 로고
    • Synthesis, structure, spectrocopic and in vitro antitumor studies of a novel gallium(III) complex with 2-acetylpyridine
    • Arion VB, Jakupec MA, Galanski M, Unfied P, Keppler BK (2002) Synthesis, structure, spectrocopic and in vitro antitumor studies of a novel gallium(III) complex with 2-acetylpyridine. J Inorg Biochem 91:298-305
    • (2002) J Inorg Biochem , vol.91 , pp. 298-305
    • Arion, V.B.1    Jakupec, M.A.2    Galanski, M.3    Unfied, P.4    Keppler, B.K.5
  • 2
    • 77954771147 scopus 로고    scopus 로고
    • Coordination to gallium(III) strongly enhances the potency of 2-pyridineformamide thiosemicarbazones against Cryptococcus opportunistic fungi
    • Bastos TO, Soares BM, Cisalpino PS, Mendes IC, Dos Santos RG, Beraldo H (2010) Coordination to gallium(III) strongly enhances the potency of 2-pyridineformamide thiosemicarbazones against Cryptococcus opportunistic fungi. Microbiol Res 165:573-577
    • (2010) Microbiol Res , vol.165 , pp. 573-577
    • Bastos, T.O.1    Soares, B.M.2    Cisalpino, P.S.3    Mendes, I.C.4    Dos Santos, R.G.5    Beraldo, H.6
  • 3
    • 3042513348 scopus 로고    scopus 로고
    • The wide pharmacological versatility of semicarbazones, thiosemicarbazones and their metal complexes
    • Beraldo H, Gambino D (2004) The wide pharmacological versatility of semicarbazones, thiosemicarbazones and their metal complexes. Mini-Rev Med Chem 4:31-39
    • (2004) Mini-Rev Med Chem , vol.4 , pp. 31-39
    • Beraldo, H.1    Gambino, D.2
  • 4
    • 0033463840 scopus 로고    scopus 로고
    • Preparation, structural characterization, and antifungal activities of complexes of group 12 metals with 2-acetylpyridine-and 2-acetylpyridine-N-oxide- 4 N-phenylthiosemicarbazones
    • Bermejo E, Castineiras A, Dominguez R, Carballo R, Maichle-Moessmer C, Straehle J, West DX (1999) Preparation, structural characterization, and antifungal activities of complexes of group 12 metals with 2-acetylpyridine-and 2-acetylpyridine-N-oxide-4 N-phenylthiosemicarbazones. Z Anorg Allg Chem 625:961-968
    • (1999) Z Anorg Allg Chem , vol.625 , pp. 961-968
    • Bermejo, E.1    Castineiras, A.2    Dominguez, R.3    Carballo, R.4    Maichle-Moessmer, C.5    Straehle, J.6    West, D.X.7
  • 5
    • 0032445152 scopus 로고    scopus 로고
    • Mechanisms of therapeutic activity for gallium
    • Bernstein LR (1998) Mechanisms of therapeutic activity for gallium. Pharmacol Rev 50:665-682
    • (1998) Pharmacol Rev , vol.50 , pp. 665-682
    • Bernstein, L.R.1
  • 7
    • 0034101581 scopus 로고    scopus 로고
    • Chemistry and pharmacokinetics of gallium maltolate, a compound with high oral gallium bioavailability
    • Bernstein LR, Tanner T, Godfrey C, Noll B (2000) Chemistry and pharmacokinetics of gallium maltolate, a compound with high oral gallium bioavailability. Met-Based Drugs 7:33-47
    • (2000) Met-Based Drugs , vol.7 , pp. 33-47
    • Bernstein, L.R.1    Tanner, T.2    Godfrey, C.3    Noll, B.4
  • 8
    • 0027476872 scopus 로고
    • Regulation of transferrin receptor expression and ferritin content in human mononuclear phagocytes. Coordinate upregulation by iron transferrin and downregulation by interferon gamma
    • Byrd TF, Horwitz MA (1993) Regulation of transferrin receptor expression and ferritin content in human mononuclear phagocytes. Coordinate upregulation by iron transferrin and downregulation by interferon gamma. J Clin Invest 91:969-976
    • (1993) J Clin Invest , vol.91 , pp. 969-976
    • Byrd, T.F.1    Horwitz, M.A.2
  • 9
    • 2642519499 scopus 로고    scopus 로고
    • Gallium nitrate for the treatment of non-Hodgkin's lymphoma
    • Chitambar CR (2004a) Gallium nitrate for the treatment of non-Hodgkin's lymphoma. Expert Opin Investig Drugs 13:531-541
    • (2004) Expert Opin Investig Drugs , vol.13 , pp. 531-541
    • Chitambar, C.R.1
  • 10
    • 14144250578 scopus 로고    scopus 로고
    • Apoptotic mechanisms of gallium nitrate: Basic and clinical investigations
    • Chitambar CR (2004b) Apoptotic mechanisms of gallium nitrate: Basic and clinical investigations. Oncology 18:39-44
    • (2004) Oncology , vol.18 , pp. 39-44
    • Chitambar, C.R.1
  • 11
    • 77952958393 scopus 로고    scopus 로고
    • A novel gallium compound synergistically enhances bortezomib-induced apoptosis in mantle cell lymphoma cells
    • Chitambar CR, Purpi DP (2010) A novel gallium compound synergistically enhances bortezomib-induced apoptosis in mantle cell lymphoma cells. Leuk Res 34:950-953
    • (2010) Leuk Res , vol.34 , pp. 950-953
    • Chitambar, C.R.1    Purpi, D.P.2
  • 13
    • 67149089295 scopus 로고    scopus 로고
    • Increasing the antibacterial activity of gallium(III) against Pseudomonas aeruginosa upon coordination to pyridine-derived thiosemicarbazones
    • Da Silva JG, Azzolini LS, Wardell SMSV, Wardell JL, Beraldo H(2009) Increasing the antibacterial activity of gallium(III) against Pseudomonas aeruginosa upon coordination to pyridine-derived thiosemicarbazones. Polyhedron 28: 2301-2305
    • (2009) Polyhedron , vol.28 , pp. 2301-2305
    • Da Silva, J.G.1    Azzolini, L.S.2    Smsv, W.3    Wardell, J.L.4    Beraldo, H.5
  • 15
    • 84860168664 scopus 로고    scopus 로고
    • Complexation of 2-acetylpyridine-and 2-benzoylpyridine-derived hydrazones to copper (II) as an effective strategy for antimicrobial activity improvement
    • Despaigne AAR, Da Costa FB, Piro OE, Castellano EE, Louro SRW, Beraldo H (2012b) Complexation of 2-acetylpyridine-and 2-benzoylpyridine-derived hydrazones to copper (II) as an effective strategy for antimicrobial activity improvement. Polyhedron 38:285-290
    • (2012) Polyhedron , vol.38 , pp. 285-290
    • Despaigne, A.A.R.1    Da Costa, F.B.2    Piro, O.E.3    Castellano, E.E.4    Louro, S.R.W.5    Beraldo, H.6
  • 16
    • 0038486137 scopus 로고    scopus 로고
    • Gallium nitrate in the treatment of bladder cancer
    • Einhorn L (2003) Gallium nitrate in the treatment of bladder cancer. Semin Oncol 30:34-41
    • (2003) Semin Oncol , vol.30 , pp. 34-41
    • Einhorn, L.1
  • 17
    • 79957675693 scopus 로고    scopus 로고
    • Interaction of triapine and related thiosemicarbazones with iron(III)/(II) and gallium(III): A comparative solution equilibrium study
    • Enyedy EA, Primik MF, Kowol CR, Arion VB, Kiss T, Keppler BK (2011) Interaction of triapine and related thiosemicarbazones with iron(III)/(II) and gallium(III): A comparative solution equilibrium study. Dalton Trans 40:5895-5905
    • (2011) Dalton Trans , vol.40 , pp. 5895-5905
    • Enyedy, E.A.1    Primik, M.F.2    Kowol, C.R.3    Arion, V.B.4    Kiss, T.5    Keppler, B.K.6
  • 18
    • 33646767009 scopus 로고    scopus 로고
    • ORTEP-3 for windows-A version of ORTEP-III with a graphical user interface (GUI
    • Farrugia LJ (1997) ORTEP-3 for Windows-a Version of ORTEP-III with a graphical user interface (GUI). J Appl Crystallogr 30:565
    • (1997) J Appl Crystallogr , vol.30 , pp. 565
    • Farrugia, L.J.1
  • 19
    • 0141452964 scopus 로고    scopus 로고
    • WinGX suite for single crystal small molecule crystallography
    • Farrugia LJ (1999) WinGX suite for single crystal small molecule crystallography. J Appl Crystallogr 32:837-838
    • (1999) J Appl Crystallogr , vol.32 , pp. 837-838
    • Farrugia, L.J.1
  • 22
    • 0033975268 scopus 로고    scopus 로고
    • Triapine (3-Aminopyridine-2-carboxaldehyde-thiosemicarbazone): A potent inhibitor of ribonucleotide reductase activity with broad spectrum antitumor activity
    • Finch RA, Liu M, Grill SP, Rose WC, Loomis R, Vasquez KM, Cheng Y, Sartorelli AC (2000) Triapine (3-Aminopyridine-2-carboxaldehyde- thiosemicarbazone): A potent inhibitor of ribonucleotide reductase activity with broad spectrum antitumor activity. Biochem Pharmacol 59:983-991
    • (2000) Biochem Pharmacol , vol.59 , pp. 983-991
    • Finch, R.A.1    Liu, M.2    Grill, S.P.3    Rose, W.C.4    Loomis, R.5    Vasquez, K.M.6    Cheng, Y.7    Sartorelli, A.C.8
  • 23
    • 0346634895 scopus 로고    scopus 로고
    • In vitro cytotoxicity testing of polycations: Influence of polymer structure on cell viability and hemolysis
    • Fisher D, Li Y, Ahlemeyer B, Krieglstein J, Kissel T (2003) In vitro cytotoxicity testing of polycations: Influence of polymer structure on cell viability and hemolysis. Biomaterials 24:1121-1131
    • (2003) Biomaterials , vol.24 , pp. 1121-1131
    • Fisher, D.1    Li, Y.2    Ahlemeyer, B.3    Krieglstein, J.4    Kissel, T.5
  • 25
    • 0036083301 scopus 로고    scopus 로고
    • Mechanism of action of antitumor drugs that interact with microtubules and tubulin
    • Jordan MA (2002) Mechanism of action of antitumor drugs that interact with microtubules and tubulin. Curr Med Chem Anticancer Agents 2:1-17
    • (2002) Curr Med Chem Anticancer Agents , vol.2 , pp. 1-17
    • Jordan, M.A.1
  • 26
    • 34147096980 scopus 로고    scopus 로고
    • The transition metal gallium disrupts Pseudomonas aeruginosa iron metabolism and has antimicrobial and antibiofilm activity
    • Kaneko Y, Thoendel M, Olakanmi O, Britigan BE, Singh PK (2007) The transition metal gallium disrupts Pseudomonas aeruginosa iron metabolism and has antimicrobial and antibiofilm activity. J Clin Invest 117:877-888
    • (2007) J Clin Invest , vol.117 , pp. 877-888
    • Kaneko, Y.1    Thoendel, M.2    Olakanmi, O.3    Britigan, B.E.4    Singh, P.K.5
  • 28
    • 33947676254 scopus 로고    scopus 로고
    • Gallium(III) and iron(III) complexes of a-N-heterocyclic thiosemicarbazones: Synthesis, characterization, cytotoxicity, and interaction with ribonucleotide reductase
    • Kowol CR, Berger R, Eichinger R, Roller A, Jakupec MA, Schmidt PP, Arion VB, Keppler BK (2007) Gallium(III) and iron(III) complexes of a-N-heterocyclic thiosemicarbazones: Synthesis, characterization, cytotoxicity, and interaction with ribonucleotide reductase. J Med Chem 50:1254-1265
    • (2007) J Med Chem , vol.50 , pp. 1254-1265
    • Kowol, C.R.1    Berger, R.2    Eichinger, R.3    Roller, A.4    Jakupec, M.A.5    Schmidt, P.P.6    Arion, V.B.7    Keppler, B.K.8
  • 29
    • 69149094267 scopus 로고    scopus 로고
    • Impact of metal coordination on cytotoxicity of 3-aminopyridine-2- carboxaldehyde thiosemicarbazone (triapine) and novel insights into terminal dimethylation
    • Kowol CR, Trondl R, Heffeter P, Arion VB, Jakupec MA, Roller A, Galanski M, Berger W, Keppler BK (2009) Impact of metal coordination on cytotoxicity of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (triapine) and novel insights into terminal dimethylation. J Med Chem 52:5032-5043
    • (2009) J Med Chem , vol.52 , pp. 5032-5043
    • Kowol, C.R.1    Trondl, R.2    Heffeter, P.3    Arion, V.B.4    Jakupec, M.A.5    Roller, A.6    Galanski, M.7    Berger, W.8    Keppler, B.K.9
  • 31
    • 78651390991 scopus 로고    scopus 로고
    • Antimony(III) complexes with pyridine-derived thiosemicarbazones: Structural studies and investigation on the antitrypanosomal activity
    • Lessa JA, Reis DC, Mendes IC, Speziali NL, Rocha LF, Pereira VRA, Melo CML, Beraldo H (2011) Antimony(III) complexes with pyridine-derived thiosemicarbazones: Structural studies and investigation on the antitrypanosomal activity. Polyhedron 30:372-380
    • (2011) Polyhedron , vol.30 , pp. 372-380
    • Lessa, J.A.1    Reis, D.C.2    Mendes, I.C.3    Speziali, N.L.4    Rocha, L.F.5    Pereira, V.R.A.6    Melo, C.M.L.7    Beraldo, H.8
  • 32
    • 84868575777 scopus 로고    scopus 로고
    • Gallium complexes as new promising metallodrug candidates
    • Lessa JA, Parrilha GL, Beraldo H (2012) Gallium complexes as new promising metallodrug candidates. Inorg Chim Acta 393:53-63
    • (2012) Inorg Chim Acta , vol.393 , pp. 53-63
    • Lessa, J.A.1    Parrilha, G.L.2    Beraldo, H.3
  • 33
    • 62549158223 scopus 로고    scopus 로고
    • Gallium(III) complexes of 2-pyridineformamide thiosemicarbazones: Cytotoxic activity against malignant glioblastoma
    • Mendes IC, Soares MA, dos Santos RG, Pinheiro C, Beraldo H (2009) Gallium(III) complexes of 2-pyridineformamide thiosemicarbazones: Cytotoxic activity against malignant glioblastoma. Eur J Med Chem 44:1870-1877
    • (2009) Eur J Med Chem , vol.44 , pp. 1870-1877
    • Mendes, I.C.1    Soares, M.A.2    Dos Santos, R.G.3    Pinheiro, C.4    Beraldo, H.5
  • 35
    • 53549110231 scopus 로고    scopus 로고
    • Identification and characterization of thiosemicarbazones antifungal and antitumor effects: Cellular iron chelation mediating cytotoxic activity
    • Opletalova V, Kalinowski DS, Vejsová M, Kunes J, Pour M, Jampi'lek J, Buchta V, Richardson DR (2008) Identification and characterization of thiosemicarbazones antifungal and antitumor effects: Cellular iron chelation mediating cytotoxic activity. Chem Res Toxicol 21:1878-1889
    • (2008) Chem Res Toxicol , vol.21 , pp. 1878-1889
    • Opletalova, V.1    Kalinowski, D.S.2    Vejsová, M.3    Kunes, J.4    Pour, M.5    Jampi'lek, J.6    Buchta, V.7    Richardson, D.R.8
  • 38
    • 0024356008 scopus 로고
    • Effects of the pH dependence of 3-[45-dimetiltiazol-2-il]-25-difenil- tetrazolium bromide-formazan absorption on chemosensitivity determined by a novel tetrazolium-based assay
    • Plumb JA, Miloroy R, Kaye SB (1989) Effects of the pH dependence of 3-[4,5-dimetiltiazol-2-il]-2,5-difenil-tetrazolium bromide-formazan absorption on chemosensitivity determined by a novel tetrazolium-based assay. Cancer Res 49:4435-4440
    • (1989) Cancer Res , vol.49 , pp. 4435-4440
    • Plumb, J.A.1    Miloroy, R.2    Kaye, S.B.3
  • 40
    • 33745823841 scopus 로고    scopus 로고
    • Ribonucleotide reductase inhibitors and future drug design
    • Shao J, Zhou B, Chu B, Yen Y (2006) Ribonucleotide reductase inhibitors and future drug design. Curr Cancer Drug Targets 6:409-431
    • (2006) Curr Cancer Drug Targets , vol.6 , pp. 409-431
    • Shao, J.1    Zhou, B.2    Chu, B.3    Yen, Y.4
  • 43
    • 58849161857 scopus 로고    scopus 로고
    • Structure validation in chemical crystallography
    • Spek AL (2009) Structure validation in chemical crystallography. Acta Crystallogr D65:148-155
    • (2009) Acta Crystallogr D65 , pp. 148-155
    • Spek, A.L.1
  • 44
    • 0038147469 scopus 로고    scopus 로고
    • Gallium nitrate in the treatment of lymphoma
    • Straus DJ (2003) Gallium nitrate in the treatment of lymphoma. Semin Oncol 30:25-33
    • (2003) Semin Oncol , vol.30 , pp. 25-33
    • Straus, D.J.1
  • 48
    • 84873405271 scopus 로고    scopus 로고
    • West Valley Road, Suite 1400, Wayne, Pennsylvania 19087-1898, USA
    • West Valley Road, Suite 1400, Wayne, Pennsylvania 19087-1898, USA


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.