Synthesis of Oxovanadium(IV) Schiff base Complexes derived from C-substituted Diamines and Pyridoxal-5-Phosphate as Antitumor Agents

Chemical Biology and Drug Design

Volumn 79, Issue 2, 2012, Pages 223-234

  Hazari, Puja Panwar ^a   Pandey, Anand Kumar ^a,b   Chaturvedi, Shubhra ^a   Tiwari, Anjani Kumar ^a   Chandna, Sudhir ^a   Dwarakanath, Bilikere Srinivasarao ^a   Mishra, Anil Kumar ^a  

^a INSTITUTE OF NUCLEAR MEDICINE AND ALLIED SCIENCES   (India)

^b BANARAS HINDU UNIVERSITY   (India)

Author keywords

Bifunctional chelating agent; Chemical nucleases; Cytotoxicity; DNA modification; Pyridoxal 5 phosphate; Schiff base; Vanadium complex

Indexed keywords

ANTINEOPLASTIC AGENT; DEOXYRIBONUCLEASE; DNA; OXOVANADIUM IV COMPLEX; SCHIFF BASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CANCER GROWTH; CANCER REGRESSION; CONTROLLED STUDY; DNA CLEAVAGE; DRUG CYTOTOXICITY; DRUG SYNTHESIS; ENZYME ACTIVITY; FEMALE; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; SUBSTITUTION REACTION;

ANIMALS; ANTINEOPLASTIC AGENTS; CARCINOMA, EHRLICH TUMOR; CELL CYCLE CHECKPOINTS; CELL LINE, TUMOR; COORDINATION COMPLEXES; DIAMINES; DNA; DNA CLEAVAGE; FEMALE; HUMANS; MICE; NEOPLASMS; OXIDATION-REDUCTION; PYRIDOXAL PHOSPHATE; SCHIFF BASES; TRANSPLANTATION, HETEROLOGOUS; VANADATES;

EID: 84855456945     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2011.01265.x     Document Type: Article

References (29)

1. Rehder D. (1991) The bioinorganic chemistry of vanadium. Angew Chem Int Ed Engl;30:148-167.
2. Butler A., Carrano C.J. (1991) Coordination chemistry of vanadium in biological systems. Chem Rev;109:61-105.
3. Larrow J.F., Jacobsen E.N. (2004) Asymmetric processes catalyzed by Chiral (Salen) metal complexes. Top Organo Chem;6:123-152.
4. El-Naggar M.M., El-Waseef A.M., El-Halafawy K.M., El-Sayed I.H. (1998) Antitumor activities of vanadium(IV), manganese(IV), iron(III), cobalt(II) and copper(II) complexes of 2-methylaminopyridine. Can Lett;133:71-76.
5. Kulkarni A.K., Patil A.S., Badami P.S. (2009) Synthesis, characterization, DNA cleavage and in vitro antimicrobial studies of La(III), Th(IV) and VO(IV) complexes with Schiff bases of coumarin derivatives. Eur J Med Chem;44:2904-2912.
6. Chohan Z.H., Sumrra S.H., Youssoufi M.H., Hadda T.B. (2010) Metal based biologically active compounds: design, synthesis, and antibacterial/antifungal/cytotoxic properties of triazole-derived Schiff bases and their oxovanadium(IV) complexes. Eur J Med Chem;45:2739-2747.
7. Hirao T. (1997) Vanadium in synthesis modern organic. Rev Chem;97:2707-2724.
8. Colpas G.J., Hamstra B., Kampf J., Pecoraro V.L. (1994) The preparation of VO3+ and VO2+ complexes using hydrolytically stable, asymmetric ligands derived from Schiff base precursors. Inorg Chem;33:4669.
9. Kostova I. (2009) Titanium and vanadium complexes as anticancer agents. Med Chem;9:827-842.
10. Evangelou A.M. (2002) Vanadium in cancer treatment. Crit Rev Oncol Hematol;42:249-265.
11. Bishayee A., Waghray A., Patel M.A., Chatterjee M. (2010) Vanadium in the detection, prevention and treatment of cancer: the in vivo evidence. Cancer Lett;294:1-12.
12. Djordjevic C. (1995) Antitumor activity of vanadium compounds. In: Sigel H., Sigel A., editors. Metal Ions in Biological Systems. New York: Marcel Dekker Publisher; p. 595-616.
13. Kwong D.W., Chan O.Y., Wong R.N., Musser S.M., Vaca L., Chan S.I. (1997) DNA-photocleavage activities of vanadium(V) - peroxo complexe. Inorg Chem;36:1276-1277.
14. Byczkowski J.Z., Wan B., Kulkarni A.P. (1988) Vanadium-mediated lipid peroxidation in microsomes from human term placenta. Bull Environ Contam Toxicol;41:696-703.
15. Sakurai H., Tamura H., Okatami K. (1995) Mechanism for a new antitumor vanadium complex: hydroxyl radical-dependent DNA cleavage by 1, 10-phenanthroline vanadyl complex in the presence of hydrogen peroxide. Biochem Biophys Res Commun;206:133-137.
16. Keller R.J., Sharma R.P., Grover T.A., Piette L.H. (1988) Vanadium and lipid peroxidation: evidence for involvement of vanadyl and hydroxyl radical. Archiv Biochem Biophys;265:524-533.
17. Ozawa T., Hanaki A. (1989) ESR evidence for the formation of hydroxyl radicals during the reaction of vanadyl ions with hydrogen peroxide. Chem Pharm Bull;37:1407-1409.
18. Richardson D.R., Milnes K. (1997) The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents II: the mechanism of action of ligands derived from salicylaldehyde benzoyl hydrazone and 2-hydroxy-1-naphthylaldehyde benzoyl hydrazone. Blood;89:3025-3038.
19. Mishra A.K., Panwar P., Chopra M., Sharma R.K., Chatal J.F. (2003) Synthesis of novel bifunctional Schiff-base ligands derived from condensation of 1-(p-nitrobenzyl)ethylenediamine and 2-(p-nitrobenzyl)-3-monooxo-1, 4, 7-triazaheptane with salicylaldehyde. New J Chem;27:1054-1058.
20. Verquin G., Fontaine G., Bria M., Zhilinskaya E., Abi-Aad E., Aboukaïs A., Baldeyrou B., Bailly C., Bernie J. (2004) DNA modifi{ligature}cation by oxovanadium(IV) complexes of salen derivative. J Biol Inorg Chem;9:345-353.
21. Rocklage S.M., Cacheris W.P., Quay S.C., Hahn F.E., Raymond K.N. (1989) Manganese(II) N, N'-dipyridoxylethylenediamine-N, N'-diacetate 5, 5'-bis(phosphate). Synthesis and characterization of a paramagnetic chelate for magnetic resonance imaging enhancement. Inorg Chem;28:477-485.
22. Laso N.M., Quiclet-Sire B., Zard S.Z. (1996) A new selective reduction of nitroalkenes into enamides. Tetrahedron Lett;37:1605-1608.
23. Hamstra B.J., Colpas G.J., Vincent P.L. (1998) Reactivity of dioxovanadium(V) complexes with hydrogen peroxide: implications for Vanadium Haloperoxidase. Inorg Chem;37:949-995.
24. Shul'pin G.B. (2002) Metal-catalyzed hydrocarbon oxygenations in solutions: the dramatic role of additives: a review. J Mol Catal A: Chemical;189:39-66.
25. Sauerheber R.D., Cochrane C.G. (1988) Mechanisms of oxidant-mediated cell injury. The glycolytic and mitochondrial pathways of ADP phosphorylation are major intracellular targets inactivated by hydrogen peroxide. J Biol Chem;263:1665-1675.
26. Narla R.K., Dong Y., D'Cruz O.J., Navara C., Uckun F.M. (2000) Bis(4, 7-dimethyl-1, 10-phenanthroline) sulfatooxovanadium(IV) as a novel apoptosis-inducing anticancer agent. Clin Cancer Res;6:1546-1556.
27. Sasmal P.K., Patra A.K., Chakravarty A.R. (2008) Synthesis, structure, DNA binding and DNA cleavage activity of oxovanadium(IV) N-salicylidene-S-methyldithiocarbazate complexes of phenanthroline bases. J Inorg Biochem;102:1463-1472.
28. Niedwieski A.C., Hitchcock P.B., Neto J.D.D.M., Wypych F., Leigh G.J., Nunes F.S. (2003) Vanadium(II)-diamine complexes: synthesis, UV-Visible, infrared, thermogravimetry, magnetochemistry and INDO/S characterisation. J Braz Chem Soc;14:750-758.
29. Bond M.R., Czernuszewicz R.S., Dave B.C., Mohan M., Verastgue R., Carrano C.J. (1995) Spectroscopic and magnetostructural correlations in oxo-bridged dinuclear vanadium(III) complexes of potential biological significance. Inorg Chem;34:5857-5869.