Enzyme inhibition, radical scavenging, and spectroscopic studies of vanadium(IV)hydrazide complexes

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 24, Issue 6, 2009, Pages 1336-1343

  Ashiq, Uzma ^a   Jamal, Rifat Ara ^a   Mahroof Tahir, Mohammad ^b   Maqsood, Zahida T ^a   Khan, Khalid Mohammed ^a   Omer, Iman ^a   Choudhary, Muhammad Iqbal ^a  

^a UNIVERSITY OF KARACHI   (Pakistan)

^b ST CLOUD STATE UNIVERSITY   (United States)

Author keywords

Free radical; Hydrazide; Nitric oxide; Phosphodiesterase; Superoxide; Vanadium

Indexed keywords

DIMETHYL SULFOXIDE; HYDRAZIDE; HYDRAZIDE DERIVATIVE; LIGAND; METAL COMPLEX; MONOMER; OXOVANADIUM COMPLEX; PHOSPHODIESTERASE I; SCAVENGER; SNAKE VENOM; SOLVENT; UNCLASSIFIED DRUG; VANADIUM; VANADIUM DERIVATIVE; VANADIUM HYDRAZIDE COMPLEX; WATER;

ARTICLE; BINDING AFFINITY; BIOTRANSFORMATION; COMPLEX FORMATION; CONTROLLED STUDY; DIMERIZATION; DRUG INHIBITION; DRUG SYNTHESIS; ELECTRONICS; ENZYME INHIBITION; INFRARED SPECTROSCOPY; MOLECULAR STABILITY; NONHUMAN; PRIORITY JOURNAL; SCAVENGING SYSTEM; SOLID STATE; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION;

CATIONS; DIMERIZATION; DIMETHYL SULFOXIDE; ENZYME INHIBITORS; FREE RADICAL SCAVENGERS; HYDRAZINES; LIGANDS; NITRIC OXIDE; ORGANOMETALLIC COMPOUNDS; PHOSPHODIESTERASE I; SPECTRUM ANALYSIS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SUPEROXIDES; VANADATES; VANADIUM;

EID: 73949127124     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756360902888168     Document Type: Article

References (51)

1. Nekola H, Wang D, Gruning C, Gatjens J, Behrens A, Rehder D. Thiofunctional vanadium complexes. Inorg Chem 2002;41:2379.
2. Buglyo P, Nagy EM, Sovago I. Vanadium(III) binding strengths of small biomolecules. Pure Appl Chem 2005;77:1583.
3. Crans DC, Smee JJ, Gaidamauskas E, Yang L. Bioinorganic vanadium chemistry. Chem Rev 2004;104:849.
4. Sheela A, Roopan SM, Vijayaraghavan R. New diketone based vanadium complexes as insulin mimetics. Eur J Med Chem 2008;43:2206.
5. Soares SS, Martins H, Gutiérrez-Merino C, Aureliano M. Vanadium and cadmium in vivo effects in teleost cardiac muscle: metal accumulation and oxidative stress markers. Comp Biochem Physiol C Toxicol Pharmacol 2008;147:168.
6. Niu Y, Liu W, Tian C, Xie M, Gao L, Chen Z, et al. Effects of bis(?cent;- furancarboxylato)oxovanadium(IV) on glucose metabolism in fat-fed/ streptozotocin-diabetic rats. Eur J Pharmacol 2007;572:213.
7. Trends in the use of V. A report of the National Materials Advisory Board, National Academy of Science, 1970, Publication NMAB-267. Springfield, VA: Clearinghouse for Federal Scientific and Technical Information, 1970:46.
8. Stern A, Yin X, Tsang SS, Davison A, Moon J. Vanadium as a modulator of cellular regulatory cascades and oncogene expression. Biochem Cell Biol 1993;71:103.
9. Fukui K, Ueki T, Ohya H, Michibata H. Vanadium-binding protein in a vanadium-rich ascidian Ascidia sydneiensissamea: CW and pulsed EPR studies. J Am Chem Soc 2003;125:6352.
10. Gresser MJ, Tracey AS, Stankiewicz PJ. The interaction of vanadate with tyrosine kinases. J Adv Protein Phosphatases 1987;4:35.
11. Sakurai H, Kojima Y, Yoshikawa Y, Kawabe K, Yasui H. Antidiabetic vanadium(IV) and zinc(II) complexes. Coord Chem Rev 2002;226:187.
12. Kawabe K, Yoshikawa Y, Adachi Y, Sakurai H. Possible mode of action for insulinomimetic activity of vanadyl(IV) compound in adipocytes. Life Sci 2006;78:2860.
13. Razzell WE. Phosphodiesterases. Methods Enzymol 1963;6:236.
14. Deutscher MP. The metabolic role of Rnases. Trends Biochem Sci 1988;13:136.
15. Deutscher MP. Ribonuclease multiplicity, diversity, and complexity. J Biol Chem 1993;268:13011.
16. Sprinkle TJ. 29,39-cyclic nucleotide 39-phosphodiesterase, an oligodendrocyte-Schwann cell and myelin-associated enzyme of the nervous system. Crit Rev Neurobiol 1989;4:235.
17. Frank R, Sucheta V, Kristen J, Ira G, Betty M, Petra S, et al. PC-1 nucleoside triphosphate pyrophosphohydrolase deficiency in idiopathic infantile arterial calcification. Am J Pathol 2001;158:543.
18. Ceriello A. Oxidative stress and glycemic regulation. Metabolism 2000;49:27.
19. Takasu N, Komiya I, Asawa T, Nagasawa Y, Yamada T. Streptozocin- and alloxan-induced H2O2 generation and DNA fragmentation in pancreatic islets. H2O2 as mediator for DNA fragmentation. Diabetes 1991;40:1141.
20. Crouch RK, Gandy SE, Kimsey G, Galbraith RA, Galbraith GM, Buse MG. The inhibition of islet superoxide dismutase by diabetogenic drugs. Diabetes 1981;30:235.
21. Kaneto H, Fujii J, Seo HG, Suzuki K, Matsuoka T, Nakamura M, et al. Apoptotic cell death triggered by nitric oxide in pancreatic beta-cells. Diabetes 1995;44:733.
22. Wolff SP, Dean RT. Glucose autoxidation and protein modification. The potential role of "autoxidative glycosylation" in diabetes. Biochem J 1987;245:243.
23. Wilson RL. Free radicals and tissue damage, mechanistic evidence from radiation studies. In: Biochemical Mechanisms of Liver Injury. New York: Academic Press, 1998:123.
24. Sekar N, Kanthasamy A, William S, Balasubramaniyan N, Govindasamy S. Antioxidant effect of vanadate on experimental diabetic rats. Acta Diabetol Lat 1990;27:285.
25. Sun Y, James BR, Retting SJ, Orvig C. Oxidation kinetics of the potent insulin mimetic agent bis(maltolato)oxovanadium(IV) (BMOV) in water and in methanol. Inorg Chem 1996;35:1667.
26. Elvingson K, Baro AG, Pettersson L. Speciation in vanadium bioinorganic systems. 2. An NMR, ESR, and potentiometric study of the aqueous H(+)- vanadate-maltol system. Inorg Chem 1996;35:3388.
27. Melchior M, Thompson KH, Jong JM, Rettig SJ, Shuter E, Yuen VG, et al. Vanadium complexes as insulin mimetic: coordination chemistry and in vivo studies of oxovanadium(IV) and dioxovanadate(V) complexes formed from naturally occurring chelating oxazolinate, thiazolinate, or picolinate units. Inorg Chem 1999;38:2288.
28. Maqsood ZT, Khan KM, Ashiq U, Jamal RA, Chohan ZH, Mahroof- Tahir M, et al. Oxovanadium(IV) complexes of hydrazides: potential antifungal agents. J Enzyme Inhib Med Chem 2006;21:37.
29. Jeffery GH, Bassett J, Denney RC. Titrimetric analysis. In: Vogel's Textbook of Quantitative Chemical Analysis, 5th ed. Harlow, UK: Longman, 1989:404.
30. Jeffery GH, Bassett J, Denney RC. Gravimetry. In: Vogel's Textbook of Quantitative Chemical Analysis, 5th ed. Harlow, UK: Longman, 1989:490.
31. Ara R, Ashiq U, Mahroof-Tahir M, Maqsood ZT, Khan KM, Lodhi MA, et al. Chemistry, urease inhibition, and phytotoxic studies of binuclear vanadium(IV) complexes. Chem Biodivers 2007;4:58.
32. Mamillapalli R, Haimovitz R, Ohad M, Shinitzky M Enhancement and inhibition of snake venom phosphodiesterase activity by lysophospholipids. FEBS Lett 1998;436:256.
33. Razzell WE, Khorana HG. Studies on polynucleotides. III. Enzymic degradation; substrate specificity and properties of snake venom phosphodiesterase. J Biol Chem 1959;234:2105.
34. Nakabayashi T, Matsuoka Y, Ikezawa H, Kimura Y. Alkaline phosphodiesterase I release from eucaryotic plasma membranes by phosphatidylinositol-specific phospholipase C-IV. The release from Cacia porcellus organs. Int J Biochem 1994;26:171.
35. Gomez JL, Costas MJ, Ribeiro JM, Fernandez A, Romero A, Avalos M, et al. Glycine-enhanced inhibition of rat liver nucleotide pyrophosphatase/ phosphodiesterase-I by EDTA: a full account of the reported inhibition by commercial preparations of acidic fibroblast growth factor (FGF-1). FEBS Lett 1998;421:77.
36. Leatherbarrow RJ. GraFit, 4.09 ed. Staines, UK: Erithacus Software Ltd, 1999.
37. Gaulejac NSC, Glories Y, Vivas N. Free radical scavenging effect of anthocyanins in red wines. Food Res Int 1999;32:327.
38. Badami S, Gupta MK, Suresh B. Antioxidant activity of the ethanolic extract of Striga orobanchioides. J Ethnopharmacol 2003;85:227.
39. Geary W. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coord Chem Rev 1971;7:81.
40. Boas LV, Pesos JC. In: Wilkinson G, Gillard RD, McCleverty JA, eds. Comprehensive Coordination Chemistry. Oxford: Pergamon Press, 1987;3:487.
41. Rao SN, Mishra DD, Maurya RC, Rao NN. Oxovanadium binuclear (IV) Schiff base complexes derived from aroyl hydrazones having subnormal magnetic moments. Polyhedron 1997;16:1825.
42. Salib KAR, Stefan SL, Abu El-Wafa SM, El-Shafiy HF. Metal complexes of novel symmetrical Schiff base ligands. Syn React Inorg Met Org Chem 2001;31:895.
43. Dutta SK, Tiekink ERT, Chaudhury M. Mono- and dinuclear oxovanadium (IV) compounds containing VO(ONS) basic core: synthesis, structure and spectroscopic properties. Polyhedron 1997;16:1863.
44. Linert W, Herlinger E, Margl P, Boca R. Spectroscopic, electrochemical and quantum mechanical investigations of vanadyl(IV)-acetylacetonate in non-aqueous solutions. J Coord Chem 1993;28:1.
45. Ghosh T, Bhattacharya S, Das A, Mukherjee G, Drew MGB. Synthesis, structure and solution chemistry of mixed-ligand oxovanadium(IV) and oxovanadium(V) complexes incorporating tridentate ONO donor hydrazone ligands. Inorg Chim Acta 2005;358:989.
46. Mahroof-Tahir M, Brezina D, Fatima N, Choudhary MI, Rahman AU. Synthesis and characterization of mononuclear oxovanadium(IV) complexes and their enzyme inhibition studies with a carbohydrate metabolic enzyme, phosphodiesterase I. J Inorg Biochem 2005;99:589.
47. Yue H, Zhang D, Shi Z, Feng S. Dinuclear oxovanadium(IV) compounds from designed amino acid derivatives. Inorg Chim Acta 2007;360:2681.
48. Xing Y-H, Zhang B-L, Zhang Y-H, Yuan H-Q, Sun Z, Ge M-F. Insulinlike model complexes: synthesis, spectra characterization and crystal structure of two novel oxovanadium complexes with poly(pyrazolyl) borate ligands, VO(HB(pz)3)(H2B(pz)2) and VO(B(pz)4)2. Polyhedron 2007;26:3037.
49. Remya PN, Suresh CH, Reddy MLP. Rapid reduction and complexation of vanadium by 1-phenyl-3-methyl-4-toluoyl-5-pyrazolone: spectroscopic characterization and structure modeling. Polyhedron 2007;26:5016.
50. Cornman CR, Zovinka EP, Meixner MH. Vanadium(IV) complexes of an active-site peptide of a protein tyrosine phosphatase. Inorg Chem 1995;34:5099.
51. Patel RN, Singh N, Shukla KK, Chauhan UK, Chakraborty S, Niclos- Gutierrez J, et al. X-ray, spectral and biological (antimicrobial and superoxide dismutase) studies of oxalato bridged CuII-NiII and CuII-ZnII complexes with pentamethyldiethylenetriamine as capping ligand. J Inorg Biochem 2004;98:231.