Metal complexes of uracil derivatives with cytotoxicity and superoxide scavenging activity

Letters in Drug Design and Discovery

Volumn 9, Issue 3, 2012, Pages 282-287

  Prachayasittikul, Supaluk ^a   Worachartcheewan, Apilak ^b   Pingaew, Ratchanok ^a   Suksrichavalit, Thummaruk ^b   Isarankura Na Ayudhya, Chartchalerm ^b   Ruchirawat, Somsak ^c   Prachayasittikul, Virapong ^b  

^a SRINAKHARINWIROT UNIVERSITY   (Thailand)

^b MAHIDOL UNIVERSITY   (Thailand)

^c Research and Innovation   (Thailand)

Author keywords

5 iodouracil; 5 nitrouracil; Metal complex; SOD and cytotoxic activities

Indexed keywords

5 IODOURACIL 8 HYDROXYQUINOLINE COPPER COMPLEX; 5 IODOURACIL 8 HYDROXYQUINOLINE MANGANESE COMPLEX; 5 IODOURACIL 8 HYDROXYQUINOLINE NICKEL COMPLEX; 5 NITROURACIL 8 HYDROXYQUINOLINE COPPER COMPLEX; 5 NITROURACIL 8 HYDROXYQUINOLINE MANGANESE COMPLEX; 5 NITROURACIL 8 HYDROXYQUINOLINE NICKEL COMPLEX; 8 QUINOLINOL DERIVATIVE; COPPER COMPLEX; DOXORUBICIN; ETOPOSIDE; FIALURIDINE; MANGANESE DERIVATIVE; METAL COMPLEX; NICKEL COMPLEX; SCAVENGER; SUPEROXIDE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

ACUTE LYMPHOBLASTIC LEUKEMIA; ANTIOXIDANT ACTIVITY; ARTICLE; BILE DUCT CARCINOMA; CANCER CELL CULTURE; CELL STRAIN HEPG2; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN TISSUE; LUNG CARCINOMA; PRIORITY JOURNAL;

EID: 84858217824     PISSN: 15701808     EISSN: 1875628X     Source Type: Journal    
DOI: 10.2174/157018012799129918     Document Type: Article

References (21)

1. Zenker, N. Thyroid function and thyroid drugs. In: Principles of Medicinal Chemistry. Foye W.O., editor, 3rd ed.; Lea & Febiger: Philadelphia, London, UK, 1990, pp. 603-621.
2. De Clercq, E.; Descamps, J.; Huang, G. F.; Torrence, P. F. 5-Nitro-2′-deoxyuridine and 5-nitro-2′-deoxyuridine 5′-monophosphate: antiviral activity and inhibition of thymidylate synthetase in vivo. Mol. Pharmacol. 1978, 14(3), 422-430. (Pubitemid 8354253)
3. Singh, U. P.; Singh, B. N.; Ghose, A. K.; Singh, R. K.; Sodhi, A. Synthesis, characterization, and antitumor activity of 5-iodouracil complexes. J. Inorg. Biochem. 1991, 44(4), 277-282.
4. Singh, V. P.; Singh, S.; Narang, K. K.; Bhattacharya, D. Aluminium(III), chromium(III) and iron(III) complexes with 5-iodouracil and 5-iodouracil- histidine and their antitumour activity. J. Enzyme Inhib. Med. Chem. 2009, 24(1), 105-110.
5. Colak, A. T.; Colak, F.; Yesilel, O. Z.; Buyukgungor, O. Synthesis, spectroscopic, thermal, voltammetric studies and biological activity of crystalline complexes of pyridine-2,6-dicarboxylic acid and 8-hydroxyquinoline. J. Mol. Struct. 2009, 936(1-3), 67-74.
6. Suksrichavalit, T.; Prachayasittikul, S.; Piacham, T.; Isarankura-Na-Ayudhya, C.; Nantasenamat, C.; Prachayasittikul, V. Copper Complexes of Nicotinic-Aromatic Carboxylic Acids as Superoxide Dismutase Mimetics. Molecules 2008, 13(12), 3040-3056.
7. Suksrichavalit, T.; Prachayasittikul, S.; Nantasenamat, C.; Isarankura-Na-Ayudhya, C.; Prachayasittikul, V. Copper complexes of pyridine derivatives with superoxide scavenging and antimicrobial activities. Eur. J. Med. Chem. 2009, 44(8), 3259-3265.
8. Zhai, S.; Yang, L.; Cui, Q. C.; Sun, Y.; Dou, Q. P.; Yan, B. Tumor cellular proteasome inhibition and growth suppression by 8-hydroxyquinoline and clioquinol requires their capabilities to bind copper and transport copper into cells. J. Biol. Inorg. Chem. 2010, 15(2), 259-269
9. Sashidhara, K. V.; Kumar, A.; Bhatia, G.; Khan, M. M.; Khanna, A. K.; Saxena, J. K. Antidyslipidemic and antioxidative activities of 8-hydroxyquinoline derived novel keto-enamine Schiffs bases. Eur. J. Med. Chem. 2009, 44(4), 1813-1818.
10. Wongsawatkul, O.; Prachayasittikul, S.; Isarankura-Na-Ayudhya, C.; Satayavivad, J.; Ruchirawat, S.; Prachayasittikul, V. Vasorelaxant and antioxidant activities of Spilanthes acmella Murr. Int. J. Mol. Sci. 2008, 9(12), 2724-2744.
11. Tengchaisri, T.; Chawengkirttikul, R.; Rachaphaew, N.; Reutrakul, V.; Sangsuwan, R.; Sirisinha, S. Antitumor activity of triptolide against cholangiocarcinoma growth in vitro and in hamsters. Cancer Lett. 1998, 133(2), 169-175. (Pubitemid 29069041)
12. II(hedta)- at the C-5 C-6 bonds. Inorg. Chem. 1992, 31(8), 1457-1462
13. 2O). J. Inorg. Biochem. 2004, 98(4), 632-638.
14. Villa, J. F.; Nelson, H. C. Synthesis, IR spectra and chelation in some copper(II) coordination compounds with 5X-uracils and 6X-2-thiouracils. J. Indian. Chem. Soc. 1978, 55, 631-636.
15. Bochkov, D. N.; Smorygo, N. A.; Shcherbakova, L. L.; Ivin, B. A. Study of heterocycles. LII. Proton NMR study of the reaction of dichlorodiammineplatinum(II) with 5-substituted uracils in DMSO. Zh. Obshch. Khim. 1984, 54, 900-905.
16. D'yachenko, S. A.; Bochkov, D. N.; Smorygo, N. A.; Stetsenko, A. I.; Studentsov, E. P.; Danevich, V. I.; Ivin, B. A. Complex compounds of platinum(II) with uracil and its derivatives. Koordinats. Khim. 1983, 9, 410-417.
17. Colak, A.; Terzi, Ü.; Col, M.; Karaoglu, Ş. A.; Karaböcek, S.; Küçükdumlu, A.; Ayaz, F. A. DNA binding, antioxidant and antimicrobial activities of homo- and heteronuclear copper(II) and nickel(II) complexes with new oxime-type ligands. Eur. J. Med. Chem. 2010, 45(11), 5169-5175.
18. Zheng, H.; Weiner, L. M.,; Bar-Am, O.; Epsztejn, S.; Cabantchik, Z. I.; Warshawsky, A.; Youdim, M. B.; Fridkin, M. Design, synthesis, and evaluation of novel bifunctional iron-chelators as potential agents for neuroprotection in Alzheimer's, Parkinson's, and other neurodegenerative diseases. Bioorg. Med. Chem. 2005, 13(3), 773-783
19. Galal, S. A.; Hegab, K. H.; Hashem, A. M.; Youssef, N. S. Synthesis and antitumor activity of novel benzimidazole-5-carboxylic acid derivatives and their transition metal complexes as topoisomerease II inhibitors. Eur. J. Med. Chem. 2010, 45(12), 5685-5691.
20. Prachayasittikul, S.; Sornsongkhram, N.; Pingaew, R.; Worachartcheewan, A.; Ruchirawat, S.; Prachayasittikul, V. Synthesis of N-substituted 5-iodouracils as antimicrobial and anticancer agents. Molecules 2009, 14(8), 2768-2779.
21. Shen, A. Y.; Chen, C. P.; Roffler, S. A chelating agent possessing cytotoxicity and antimicrobial activity: 7-morpholinomethyl-8-hydroxyquinoline. Life Sci. 1999, 64(9), 813-825 (Pubitemid 29098976)