Thermal degradation behavior of some ruthenium complexes with fluoroquinolone derivatives as potential antitumor agents
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Abstract
Three new complexes with ligands belong to the fluoroquinolone class having the general formula [RuL2Cl2]Cl nH2O ((1) L: norfloxacin (nf), n = 4; (2) L: ciprofloxacin (cp), n = 3; (3) L: enrofloxacin (enro), n = 5) were synthesized and characterized by chemical analysis UV–Vis and IR spectroscopy. In all complexes fluoroquinolone derivative acts as bidentate chelate ligand. The thermal behavior steps were investigated in synthetic air flow. The thermal transformations are complex processes according to TG and DTG curves including dehydration, quinolone derivative degradation, as well as RuCl3 conversion in RuO2.
Keywords
Fluoroquinolone Ruthenium complexes Thermal behaviorNotes
Acknowledgements
This study was partially supported by the PNII Grant no. 61-48/2007 of the Romanian Ministry of Education and Research.
References
- 1.Levine C, Hiasa H, Mariabs KJ. Biochim Biophys Acta. 1998;1400:29–43.Google Scholar
- 2.Drlica K. Mechanism of fluoroquinolone action. Curr Opin Microbiol. 1999;2:504–8.CrossRefGoogle Scholar
- 3.Drlica K, Zhao X. DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev. 1997;61:377–92.Google Scholar
- 4.Buchbinder M, Webb JC, Anderson LV, McCabe WR. Laboratory studies and clinical pharmacology of nalidixic acid (WIN 18, 320). Antimicrob Agents Chemother. 1962;2:308–17.Google Scholar
- 5.Andriole V. The quinolones. New York: Academic Press; 1999.Google Scholar
- 6.Cheng D, Xu WR, Liu CX. Relationship of quantitative structure and pharmacokinetics in fluoroquinolone antibacterials. World J Gastroenterol. 2007;13:2496–503.Google Scholar
- 7.Oliphant CM, Green GM. Quinolones: a comprehensive review. Am Fam Physician. 2002;65:455–64.Google Scholar
- 8.Souza MJ, Bittencourt CF, Morsch LM. LC determination of enrofloxacin. J Pharm Biomed Anal. 2002;28:1195–9.CrossRefGoogle Scholar
- 9.Fan JY, Sun D, Yu H, Kerwin SM, Hurley LH. Self-assembly of a quinobenzoxazine-Mg2+ complex on DNA a new paradigm for the structure of a drug-DNA complex and implications for the structure of the quinolone bacterial gyrase-DNA complex. J Med Chem. 1995;38:408–24.CrossRefGoogle Scholar
- 10.Ameyama S, Shinmura Y, Takahata M. Inhibitory activities of quinolones against DNA gyrase of Chlamydia pneumoniae. Antimicrob Agents Chemother. 2003;47:2327–9.CrossRefGoogle Scholar
- 11.Al-Mustafa J. Magnesium, calcium and barium perchlorate complexes of ciprofloxacin and norfloxacin. Acta Chim Slov. 2002;49:457–66.Google Scholar
- 12.Sadeek SA. Synthesis, thermogravimetric analysis, infrared, electronic and mass spectra of Mn(II), Co(II) and Fe(III) norfloxacin complexes. J Mol Struct. 2005;753:1–12.CrossRefGoogle Scholar
- 13.Jiménez-Garrido N, Perelló L, Ortiz R, Alzuet G, González-Álvarez M, Cantón E, Liu-González M, García-Granda S, Pérez-Priede M. Antibacterial studies, DNA oxidative cleavage, and crystal structures of Cu(II) and Co(II) complexes with two quinolone family members, ciprofloxacin and enoxacin. J Inorg Biochem. 2005;99:677–89.CrossRefGoogle Scholar
- 14.Vieira LMM, de Almeida MV, Lourenço MCS, Bezerra FAFM, Fontes APS. Synthesis and antitubercular activity of palladium and platinum complexes with fluoroquinolones. Eur J Inorg Chem. 2009;44:4107–11.Google Scholar
- 15.Ruíz P, Ortiz R, Perelló LL, Alzuet G, González-Álvarez M, Liu-González M, Sanz-Ruíz F. Synthesis, structure, and nuclease properties of several binary and ternary complexes of copper(II) with norfloxacin and 1, 10 phenantroline. J Inorg Biochem. 2007;101:831–40.CrossRefGoogle Scholar
- 16.Refat MS, Mohamed GG, de Farias RF, Powell AK, Mohamed MS, El-Korashy SA, Hussien MA. Spectroscopic, thermal and kinetic studies of coordination compounds of Zn(II), Cd(II) and Hg(II) with norfloxacin. J Therm Anal Calorim. 2010;102:225–32. doi: 10.1007/s10973-009-0404-x.CrossRefGoogle Scholar
- 17.López-Gresa MP, Ortiz R, Perelló L, Latorre J, Liu-González M, García-Granda S, Pérez-Priede M, Cantón E. Interactions of metal ions with two quinolone antimicrobial agents (cinoxacin and ciprofloxacin). Spectroscopic and X-ray structural characterization. Antibacterial studies. J Inorg Biochem. 2002;92:65–74.CrossRefGoogle Scholar
- 18.Obaleye JA, Akinremi CA, Balogun EA, Adebayo JO. Toxicological studies and antimicrobial properties of some iron(III) complexes of ciprofloxacin. Afr J Biotechnol. 2007;6:2826–32.Google Scholar
- 19.Clarke MJ, Zhu FC, Frasca DR. Non-platinum chemotherapeutic metallopharmaceuticals. Chem Rev. 1999;99:2511–33.CrossRefGoogle Scholar
- 20.Durig JR, Danneman J, Behnke WD, Mercer EE. The induction of filamentous growth in Escherichia coli by ruthenium and palladium complexes. Chem Biol Interact. 1976;13:287–94.CrossRefGoogle Scholar
- 21.Bergamo A, Gava B, Alessio E, Mestroni G, Serli B, Cocchietto M, Zorzet S, Sava G. Ruthenium-based NAMI-A type complexes with in vivo selective metastasis reduction and in vitro invasion inhibition unrelated to cell cytotoxicity. Int J Oncol. 2002;21:1331–8.Google Scholar
- 22.Lipponer KG, Vogel E, Keppler BK. Synthesis, characterization and solution chemistry of transindazoliumtetrachlorobis(indazole)ruthenate(III), a new anticancer ruthenium complex. IR, UV, NMR, HPLC investigations and antitumor activity. Crystal structures of trans-l-methylindazoliumtetrachlorobis-(1-methylindazole)ruthenate(III) and its hydrolysis product trans-monoaquatrichlorobis-(1-methylindazole)-ruthenate(III). Met Based Drugs. 1996;3:243–60.CrossRefGoogle Scholar
- 23.Hartinger CG, Zorbas-Seifried S, Jakupec M, Kynast B, Zorbas H, Keppler BK. From bench to bedside–preclinical and early clinical development of the anticancer agent indazolium trans-[tetrachlorobis(1H-indazole)ruthenate(III)] (KP1019 or FFC14A). J Inorg Biochem. 2006;100:891–904.CrossRefGoogle Scholar
- 24.Scherzer J, Clapp LB. Ruthenium complexes with ethylenediaminetetraacetic acid. J Inorg Nucl Chem. 1968;30:1107–9.CrossRefGoogle Scholar
- 25.Matsubara T, Creutz C. Properties and reactivities of pentadentate ethylenediaminetetraacetate complexes of ruthenium(III) and -(II). Inorg Chem. 1979;18:1956–66.CrossRefGoogle Scholar
- 26.Vilaplana-Serrano R, Basallote MG, Ruiz-Valero C, Gutiérrez-Puebla E, González-Vílchez F. Synthesis and X-ray structural study of a novel ruthenium (III)–ethylenediaminetetraacetate complex. The first compound showing an unusual coordination site for a carboxylic (glycine) group. J Chem Soc Chem Commun. 1991;100–1.Google Scholar
- 27.González-Vílchez F, Vilaplana R, Blasco G, Messori L. Solution studies of the antitumor complex dichloro 1, 2-propylendiaminetetraacetate ruthenium (III) and of its interactions with proteins. J Inorg Biochem. 1998;71:45–51.CrossRefGoogle Scholar
- 28.Badea M, Olar R, Marinescu D, Uivarosi V, Nicolescu TO, Iacob D. Thermal study of some new quinolone ruthenium (III) complexes with potential cytostatic activity. J Therm Anal Calorim. 2010;99:829–34.CrossRefGoogle Scholar
- 29.Badea M, Olar R, Marinescu D, Uivarosi V, Iacob D. Thermal decomposition of some biologically active complexes of ruthenium (III) with quinolone derivatives. J Therm Anal Calorim. 2009;97:735–9.CrossRefGoogle Scholar
- 30.Deacon GB, Philips JR. Relationships between the carbon-oxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination. Coord Chem Rev. 1980;33:227–50.CrossRefGoogle Scholar
- 31.Lever ABP. Inorganic electronic spectroscopy. Amsterdam, London, New York: Elsevier; 1986. p. 454.Google Scholar
- 32.Zhang JJ, Ge LG, Zhang XL, Dai YJ, Chen HL, Mo PL. Thermal decomposition kinetics of the Zn(II) complex with norfloxacin in static air atmosphere. J Therm Anal Calorim. 1999;58:269–78.CrossRefGoogle Scholar
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