Identification and characterization of novel tissue-nonspecific alkaline phosphatase inhibitors with diverse modes of action

Journal of Biomolecular Screening

Volumn 14, Issue 7, 2009, Pages 824-837

  Sergienko, Eduard ^b   Su, Ying ^a   Chan, Xochella ^a   Brown, Brock ^a   Hurder, Andrew ^b   Narisawa, Sonoko ^c   Mill̀n, José Luis ^a  

^a EASTERN VIRGINIA MEDICAL SCHOOL   (United States)

^b BURNHAM INSTITUTE   (United States)

^c DIVERSA CORPORATION   (United States)

Author keywords

Compound selectivity; Diverse MOA; MLSCN; MLSMR; NIH Roadmap Initiatives; TNAP inhibitors

Indexed keywords

ALKALINE PHOSPHATASE INHIBITOR; ENZYME INHIBITOR; MLS 0005718; MLS 0010847; MLS 0038949; MLS 0039961; MLS 0043344; MLS 0043574; MLS 0067142; UNCLASSIFIED DRUG;

ARTICLE; COLORIMETRY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG STRUCTURE; ENZYME SUBSTRATE; KNOWLEDGE; LABORATORY; LUMINESCENCE; MOLECULAR LIBRARY; PRIORITY JOURNAL; PROTEIN EXPRESSION; SCREENING;

ALKALINE PHOSPHATASE; ANIMALS; BIOCATALYSIS; CERCOPITHECUS AETHIOPS; COLORIMETRY; COS CELLS; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; HIGH-THROUGHPUT SCREENING ASSAYS; LUMINESCENT MEASUREMENTS; ORGAN SPECIFICITY; REPRODUCIBILITY OF RESULTS; SUBSTRATE SPECIFICITY; SULFANILAMIDES;

EID: 69549133313     PISSN: 10870571     EISSN: 1552454X     Source Type: Journal    
DOI: 10.1177/1087057109338517     Document Type: Article

References (38)

1. McComb RB, Bowers GN Jr, Posen S.: Alkaline Phosphatase. New York: Plenum, 1979.
2. Mill̀n JL: Mammalian Alkaline Phosphatases: From Biology to Applications in Medicine and Biotechnology. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co, 2006.
3. Russell RGG, Bisaz S., Fleisch H.: Pyrophosphate and diphosphates in calcium metabolism and their possible role in renal failure. Arch Intern Med 1969 ; 124: 571-575.
4. Meyer JL: Can biological calcification occur in the presence of pyrophosphate? Arch Biochem Biophys 1984 ; 231: 1-8.
5. Francis MD, Russell RGG, Fleisch H.: Diphosphonates inhibit formation of calcium phosphate crystals in vitro and pathologic calcification in vivo. Science 1969 ; 165: 1264-1266.
6. Lomashvili KA, Cobbs S., Hennigar RA, Hardcastle KI, O'Neill WC: Phosphate-induced vascular calcification: role of pyrophosphate and osteopontin. J Am Soc Nephrol 2004 ; 15: 1392-1401.
7. Schibler D., Russell GG, Fleisch H.: Inhibition by pyrophosphate and polyphosphate of aortic calcification induced by vitamin D3 in rats. Clin Sci 1968 ; 35: 363-372.
8. Garg P., Lomashvili KA, O'Neill WC: Uremic vascular calcification: role of pyrophosphate deficiency and prevention by bisphosphonate therapy. J Am Soc Nephrol 2005 ; 16: 53.
9. Terkeltaub RA: Inorganic pyrophosphate generation and disposition in pathology. Am J Physiol 2001 ; 281: C1 - C11.
10. Rutsch F., Vaingankar S., Johnson K., Goldfine I., Maddux B., Schauerte P., et al. PC-1 nucleoside triphosphate pyrophosphohydrolase deficiency in idiopathic infantile arterial calcification. Am J Pathol 2001 ; 158: 543-554.
11. Rutsch F., Ruf N., Vaingankar S., Toliat MR, Suk A., Hohne W., et al. Mutations in ENPP1 are associated with "idiopathic" infantile arterial calcification. Nat Genet 2003 ; 34: 379-381.
12. Lomashvili KA, Khawandi W., O'Neill WC: Reduced plasma pyrophosphate levels in hemodialysis patients. J Am Soc Nephrol 2005 ; 16: 2495-2500.
13. Hessle L., Johnson KA, Anderson HC, Narisawa S., Sali A., Goding JW, et al. Tissue-nonspecific alkaline phosphatase and plasma cell membrane glycoprotein-1 are central antagonistic regulators of bone mineralization. Proc Natl Acad Sci USA 2002 ; 99: 9445-9449.
14. Harmey D., Hessle L., Narisawa S., Johnson KA, Terkeltaub RA, Mill̀n JL: Concerted regulation of inorganic pyrophosphate and osteopontin by Akp2, Enpp1 and Ank: an integrated model of the pathogenesis of mineralization disorders. Am J Pathol 2004 ; 164: 1199-1209.
15. Hsu HH, Camacho NP: Isolation of calcifiable vesicles from human atherosclerotic aortas. Atherosclerosis 1999 ; 143: 353-362.
16. Hui M., Li SQ, Holmyard D., Cheng P.: Stable transfection of nonosteogenic cell lines with tissue nonspecific alkaline phosphatase enhances mineral deposition both in the presence and absence of beta-glycerophosphate: possible role for alkaline phosphatase in pathological mineralization. Calcif Tissue Int 1997 ; 60: 467-472.
17. Tanimura A., McGregor DH, Anderson HC: Calcification in atherosclerosis I. Human studies. J Exp Pathol 1986 ; 2: 261-273.
18. Shioi A., Nishizawa Y., Jono S., Koyama H., Hosoi M., Morii H.: Beta-glycerophosphate accelerates calcification in cultured bovine vascular smooth muscle cells. Arterioscler Thromb Vasc Biol 1995 ; 15: 2003-2009.
19. Shioi A., Katagi M., Okuno Y., Mori K., Jono S., Koyama H., et al. Induction of bone-type alkaline phosphatase in human vascular smooth muscle cells: roles of tumor necrosis factor-alpha and oncostatin M derived from macrophages. Circ Res 2002 ; 91: 9-16.
20. Narisawa S., Harmey D., Yadav MC, O'Neill WC, Hoylaerts MF, Mill̀n JL: High throughput screening and identification of novel alkaline phosphatase inhibitors: a druggable target for the treatment of vascular calcification. J Bone Miner Res 2007 ; 22: 1700-1710.
21. Lomashvili KA, Garg P., Narisawa S., Mill̀n JL, O'Neill WC: Upregulation of alkaline phosphatase and pyrophosphate hydrolysis: potential mechanism for uremic vascular calcification. Kidney Int 2008 ; 73: 1024-1030.
22. Holtz KM, Stec B., Kantrowitz ER: A model of the transition state in the alkaline phosphatase reaction. J Biol Chem 1999 ; 274: 8351-8354.
23. Stinson RA: Kinetic parameters for the cleaved substrate, and enzyme and substrate stability, vary with the phosphoacceptor in alkaline phosphatase catalysis. Clin Chem 1993 ; 39: 2293-2297.
24. Fishman WH, Sie H-G.: Organ-specific inhibition of human alkaline phosphatase isoenzymes of liver, bone, intestine and placenta; L-phenylalanine, L-tryptophan and L-homoarginine. Enzymologia 1971 ; 41: 141-167.
25. Van Belle H.: Alkaline phosphatase: I. Kinetics and inhibition by levamisole of purified isoenzymes from humans. Clin Chem 1976 ; 22: 972-976.
26. Farley JR, Ivey JL, Baylink DJ: Human skeletal alkaline phosphatase: kinetic studies including pH dependence and inhibition by theophylline. J Biol Chem 1980 ; 255: 4680-4686.
27. Kozlenkov A., Hoylaerts MF, Ny T., Le Du MH, Mill̀n JL: Residues determining the binding specificity of uncompetitive inhibitors to tissue-nonspecific alkaline phosphatase. J Bone Min Res 2004 ; 19: 1862-1872.
28. Sergienko EA, Mill̀n JL: Screening for novel inhibitors of alkaline phosphatase of diverse modes of action. Nat Protocols. In press.
29. Cogan EB, Birrell GB, Griffith OH: A robotics-based automated assay for inorganic and organic phosphates. Anal Biochem 1999 ; 271: 29-35.
30. Zhang JH, Chung TDY, Oldenburg KR: A simple statistical parameter for use in evaluation and validation of high throughput screening assays. J Biomol Screen 1999 ; 4: 67-73.
31. Ardecky R., Sidique S., Su Y., Narisawa S., Brown B., Millan JL, et al. Design and synthesis of pyrazole derivatives as potent and selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP). Bioorg Med Chem Lett 2009 ; 19: 222-225.
32. Austin CP, Brady LS, Insel TR, Collins FS: Molecular biology: NIH Molecular Libraries initiative. Science 2004 ; 306: 1138-1139.
33. Moss DW, Eaton RH, Smith JK, Whitby LG: Association of inorganic pyrophosphatase activity with human alkaline phosphatase preparations. Biochem J 1967 ; 102: 53-57.
34. Whyte MP, Mahuren JD, Fedde KN, Cole FS, McCabe ER, Coburn SP: Perinatal hypophosphatasia: tissue levels of vitamin B6 are unremarkable despite markedly increased circulating concentrations of pyridoxal-5-2phosphate: evidence for an ectoenzyme role for tissue-nonspecific alkaline phosphatase. J Clin Invest 1988 ; 81: 1234-1239.
35. Fedde KN, Blair L., Silverstein J., Coburn SP, Ryan LM, Weinstein RS, et al. Alkaline phosphatase knock-out mice recapitulate the metabolic and skeletal defects of infantile hypophosphatasia. J Bone Miner Res 1999 ; 14: 2015-2026.
36. Mill̀n JL, Narisawa S., Lemire I., Loisel TP, Boileau G., Leonard P., et al. Enzyme replacement therapy for murine hypophosphatasia. J Bone Miner Res 2008 ; 23: 777-787.
37. WHO Guidelines on Standard Operating Procedures for Clinical Chemistry, Section B. Retrieved from: http://www.searo.who.int/EN/Section10/Section17/ Section53/Section481-1761.htm
38. Lazo JS, Brady LS, Dingledine R.: Building a pharmacological lexicon: small molecule discovery in academia. Mol Pharmacol 2007 ; 72: 1-7.