Alkaline phosphatase inhibition by vanadyl-β-diketone complexes: electron density effects

References

• P Llinas, M Masella, T Stigbrand, A Menez, EA Stura, and MH Le Du. (2006). Structural studies of human alkaline phosphatase in complex with strontium: Implication for its secondary effect in bones. Pro Sci 15:1691–1700.
   Google Scholar
• EE Kim, and HW Wyckoff. (1991). Reaction mechanism of alkaline phosphatase based on crystal structures. J Mol Biol 218:449–464.
   PubMed Web of Science ®Google Scholar
• M DeBacker, S McSweeny, HB Rasmussen, BW Riise, P Lindley, and E Hough. (2002). The 1.9 Å crystal structure of heat-labile shrimp alkaline phosphatase. J Mol Biol 318:1265–1274.
   PubMedGoogle Scholar
• MH Le Du, T Stigbrand, MT Taussig, A Menez, and EA Stura. (2001). Crystal structure of alkaline phosphatase from human placenta at 1.8 Å resolution. Implication for substrate specificity. J Biol Chem 276:9158–9165.
   PubMed Web of Science ®Google Scholar
• D Chappelet-Tordo, M Fosset, M Iwatsubo, C Gache, and M Lazdunski. (1974). Intestinal alkaline phosphatase. Catalytic properties and half of the sites reactivity. Biochemistry 13:1788–1795.
   PubMed Web of Science ®Google Scholar
• M Fosset, D Chappele, and M Lazdunsk. (1974). Intestinal alkaline-phosphatase-physical-properties and quaternary structure. Biochemistry 13:1783–1788.
   PubMed Web of Science ®Google Scholar
• P Portmann, A Jorg, K Furrer, HS Walker, P Leuthard, JF Sudan, F Perriard, JF Comment, G Leva, and JP Nell. (1982). Calf intestinal alkaline-phosphatase .1. Improved isolation method and molar composition of the purified phosphatase. Helv Chim Acta 65:2668–2681.
   Google Scholar
• GAD Miggiano, A Mordente, GE Martorana, and A Castelli. (1985). Modification of arginine residues in calf intestinal alkaline-phosphatase. Ital J Biochem 34:364–372.
   PubMedGoogle Scholar
• G Schmidt, and SJ Thannhauser. (1943). Intestinal phosphatase. J Biol Chem 149:369–385.
   Google Scholar
• HN Fernley, and PG Walker. (1967). Studies on alkaline phosphatase. Inhibition by phosphate derivatives and the substrate specificity. Biochem J 104:1011–1018.
   PubMed Web of Science ®Google Scholar
• HA Ensinger, HE Pauly, G Pfleiderer, and T Stiefel. (1978). Role of Zn(II) in calf intestinal alkaline-phosphatase studied by influence of chelating-agents and chemical modification of histidine residues. Biochim et Biophy Acta 527:432–441.
   PubMedGoogle Scholar
• KM Holtz, B Stec, and ER Kantrowitz. (1999). A model of the transition state in alkaline phosphatase reaction. J Biol Chem 274:8351–8354.
   PubMedGoogle Scholar
• DC Crans, AD Keramidas, and C Drouza. (1996). Organic vanadium compounds – transition state analogy with organic phosphorus compounds. Phosphorus Sulfur Silicon 109–110:245–248.
   Google Scholar
• H Sakurai, A Katoh, and Y Yoshikawa. (2006). Chemistry and biochemistry of insulin-mimetic vanadium and zinc complexes. Trial for treatment of diabetes mellitus. Bull Chem Soc Jpn 79:1645–1664.
   Web of Science ®Google Scholar
• DC Crans, JJ Smee, E Gaidamauskas, and L Yang. (2004). The chemistry and biochemistry of vanadium and the biological activities exerted by vanadium compounds. Chem Rev 104:849–902.
   PubMed Web of Science ®Google Scholar
• MW Makinen, and MJ Brady. (2002). Structural origins of insulin-mimetic activity of bis(acetylacetonate)oxovanadium(IV). J Biol Chem 277:12215–12220.
   PubMedGoogle Scholar
• BA Reul, SS Amin, JP Buchet, LN Ongemba, DC Crans, and SM Brichard. (1999). Effects of vanadium complexes with organic ligands on glucose metabolism: A comparison study in diabetic rats. Brit J Pharm 126:467–477.
   PubMed Web of Science ®Google Scholar
• SS Amin, K Cryer, B Zhang, SK Dutta, SS Eaton, OP Anderson, SM Miller, BA Reul, SM Brichard, and DC Crans. (2000). Chemistry and insulin-mimetic properties of bis(acetylacetonate)oxovanadium(IV) and derivatives. Inorg Chem 39:404–416.
   Google Scholar
• A Katoh, M Yamaguchi, R Saito, Y Adachi, and H Sakurai. (2004). Insulinomimetic vanadyl-hydroxythiazolethione complexes with VO(S2O2) coordination mode: The correlation between the activity and Hammett's substituent constant. Chem Lett 33:1274–1275.
   Web of Science ®Google Scholar
• JCH Byon, AB Kusari, and J Kusari. (1998). Protein-tyrosine phosphatase-1B acts as a negative regulator of insulin signal transduction. Mol Cell Biochem 182:101–108.
   PubMed Web of Science ®Google Scholar
• MM Jones. (1954). Some vanadyl complexes with β-diketones. J Amer Chem Soc 76:5995–5997.
   Google Scholar
• OA Odunola, and JAO Woods. (2001). Synthesis, electronic, and magnetic properties of some 3-substituted 2, 4-pentanedionatooxovanadium(IV) complexes and their 4-methylpyridine adducts. Synth React Inorg Metal-Org Chem 31:1297–1310.
   Google Scholar
• RP Dodge, DH Templeton, and A Zalkin. (1961). Crystal structure of vanadyl bisacetylacetonate: Geometry of vanadium in fivefold coordination. J Chem Phys 35:55–67.
   Web of Science ®Google Scholar
• DC Crans, AS Tracey. The chemistry of vanadium in aqueous and non-aqueous solution. In: AS Tracey, and DC Crans, editors. Vanadium compounds: Chemistry, biochemistry, and therapeutic applications., Vol 711 USA: Oxford University Press; (1998). p 11.
   Google Scholar
• MSDS online, p 94 [Internet]., Vanadyl(IV)-Acetylacetonate, Acros Organic N.V., Fair Lawn, NJ. 2007 Apr 4 - [cited 2007 Oct 31]; Available from: http://www.msdsonline.com.
   Google Scholar
• RDB Fraser, E Susuki. In: SJ Leach, editor. Physical principles and techniques of protein chemistry. New York: Academic Press; (1973); 301–355. Part C.
   Google Scholar
• AD Becke. (1993). Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652.
   Web of Science ®Google Scholar
• C Lee, W Yang, and RG Parr. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789.
   PubMed Web of Science ®Google Scholar
• B Mennucci, E Cances, and J Tomasi. (1997). Evaluation of solvent effects in isotropic and anisotropic dielectrics and in ionic solutions with a unified integral equation method: Theoretical bases, computational implementation, and numerical applications. J Phys Chem B 101:10506–10517.
   Web of Science ®Google Scholar
• G Rauhut, and P Pulay. (1995). Transferable scaling factors for density functional derived vibrational force fields. J Phys Chem 99:3093–3100.
   Web of Science ®Google Scholar
• Gaussian03. Revision C.02. Wallingford, CT: Gaussian Inc. (2004).
   Google Scholar
• F Daniels, RA Alberty. Physical chemistry. 2nd ed.. New York: Wiley and Sons Inc. (1961); 649–652.
   Google Scholar
• G Cathala, C Brunel, D Chappelet-Tordo, and M Lazdunski. (1975). Bovine kidney alkaline phosphatase catalytic properties, subunit interactions in the catalytic process, and mechanism of Mg2+ stimulation. J Biol Chem 250:6046–6053.
   PubMed Web of Science ®Google Scholar
• JE Huheey. Inorganic chemistry. 3rd ed.. New York: Harper and Row; (1983). p 156.
   Google Scholar