Novel inhibitors of alkaline phosphatase suppress vascular smooth muscle cell calcification

Journal of Bone and Mineral Research

Volumn 22, Issue 11, 2007, Pages 1700-1710

  Narisawa, Sonoko ^a   Harmey, Dympna ^a   Yadav, Manisha C ^a   O'Neill, W Charles ^b   Hoylaerts, Marc F ^c   Millán, Jose Luis ^a  

^a BURNHAM INSTITUTE   (United States)

^b EMORY UNIVERSITY   (United States)

^c UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Chemical library screening; Computer modeling; Docking; Druggable target; Pyrophosphatase; Vascular calcification

Indexed keywords

1,2 DIPHENYL 2 (1H 1,2,4 TRIAZOL 5 YLTHIO)ATHANONE; 6 [(1 METHYL 1H IMIDAZOL 2 YL)THIO] N,N1 DIPHENYL 1,3,5 TRIAZINE 2,4 DIAMINE; ALKALINE PHOSPHATASE; COMPOUND 5361418; COMPOUND 5804079; COMPOUND 5923412; ENZYME INHIBITOR; IMIDAZOLE DERIVATIVE; INORGANIC PYROPHOSPHATASE; LEVAMISOLE; N (2 PHENOXYETHYL) 2 (4H 1,2,4 TRIAZOL 3 YLTHIO)ACETAMIDE; PYROPHOSPHATE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; 5361418 COMPOUND; 5804079 COMPOUND; 5923412 COMPOUND; ECTONUCLEOTIDE PYROPHOSPHATASE PHOSPHODIESTERASE 1; PHOSPHODIESTERASE; TRIAZINE DERIVATIVE;

ALKALINITY; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BLOOD VESSEL CALCIFICATION; CELL STRAIN COS1; COMPUTER MODEL; CONTROLLED STUDY; DISEASE MODEL; DRUG IDENTIFICATION; DRUG POTENCY; DRUG SCREENING; DRUG SPECIFICITY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; HIGH THROUGHPUT SCREENING; HYDROLYSIS; MINERALIZATION; NONHUMAN; OSTEOARTHRITIS; PHENOTYPE; RAT; SMOOTH MUSCLE FIBER; SOFT TISSUE CALCIFICATION; STRUCTURE ANALYSIS; VASCULAR SMOOTH MUSCLE; ANIMAL; AORTA DISEASE; BINDING SITE; CALCINOSIS; CELL CULTURE; CHEMISTRY; CYTOLOGY; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; GENETICS; HUMAN; MOUSE; MOUSE MUTANT; PATHOLOGY;

ALKALINE PHOSPHATASE; ANIMALS; AORTIC DISEASES; BINDING SITES; CALCINOSIS; CELLS, CULTURED; ENZYME INHIBITORS; HUMANS; IMIDAZOLES; MICE; MICE, MUTANT STRAINS; MUSCLE, SMOOTH, VASCULAR; MYOCYTES, SMOOTH MUSCLE; OSTEOARTHRITIS; PHOSPHORIC DIESTER HYDROLASES; PYROPHOSPHATASES; TRIAZINES; TRIAZOLES;

EID: 37349053032     PISSN: 08840431     EISSN: None     Source Type: Journal    
DOI: 10.1359/jbmr.070714     Document Type: Article

References (46)

1. Detrano RC, Doherty TM, Davies MJ, Stary HC 2000 Predicting coronary events with coronary calcium: Pathophysiologic and clinical problems. Curr Probl Cardiol 25:374-402.
2. Wallin R, Wajih N, Greenwood GT, Sane DC 2001 Arterial Calcification: A review of mechanisms, animal models and the prospects for therapy. Med Res Rev 21:274-301.
3. Towler D 2005 Inorganic pyrophosphate - a paracrine regulator of vascular calcification and smooth muscle phenotype. Arterioscler Thromb Vasc Biol 25:651-654.
4. Terkeltaub RA 2001 Inorganic pyrophosphate generation and disposition in pathology. Am J Physiol Cell Physiol 281:C1-C11.
5. Meyer JL 1984 Can biological calcification occur in the presence of pyrophosphate? Arch Biochem Biophys 231:1-8.
6. Lomashvili K, Cobbs S, Hennigar R, Hardcastle K, O'Neill WC 2004 Phosphate-induced vascular calcification: Role of pyrophosphate and osteopontin. J Am Soc Nephrol 15:1392-1401.
7. Johnson K, Polewski M, van Etten D, Terkeltaub R 2005 Chondrogenesis mediated by PPi depletion promotes spontaneous aortic calcification in NPP1-/- mice. Arterioscler Thromb Vasc Biol 25:686-691.
8. Okawa A, Nakamura I, Goto S, Moriya H, Nakamura Y, Ikegawa S 1998 Mutation in Npps in a mouse model of ossification of the posterior longitudinal ligament of the spine. Nat Genet 19:271-273.
9. Rutsch F, Vaingankar S, Johnson K, Goldfine I, Maddux B, Schauerte P, Kalhoff H, Sano K, Boisvert WA, Superti-Furga A, Terkeltaub R 2001 PC-1 nucleoside triphosphate pyrophosphohydrolase deficiency in idiopathic infantile arterial calcification. Am J Pathol 158:543-554.
10. Rutsch F, Ruf N, Vaingankar S, Toliat MR, Suk A, Hohne W, Schauer G, Lehmann M, Roscioli T, Schnabel D, Epplen JT, Knisely A, Superti-Furga A, McGill J, Filippone M, Sinaiko AR, Vallance H, Hinrichs B, Smith W, Ferre M, Terkeltaub R, Nurnberg P 2003 Mutations in Enpp1 are associated with 'idiopathic' infantile arterial calcification. Nat Genet 34:379-381.
11. Ho AM, Johnson MD, Kingsley DM 2000 Role of the mouse ank gene in control of tissue calcification and arthritis. Science 289:265-270.
12. Harmey D, Hessle L, Narisawa S, Johnson K, Terkeltaub R, Millán JL 2004 Concerted regulation of inorganic pyrophosphate and osteopontin by Akp2, Enpp1 and Ank. An integrated model of the pathogenesis of mineralization disorders. Am J Pathol 164:1199-1209.
13. Millán JL 2006 Mammalian Alkaline Phosphatases. From Biology to Applications in Medicine and Biotechnology. Wiley-VCH Verlag, Weinheim, Germany.
14. Johnson KA, Hessle L, Wennberg C, Mauro S, Narisawa S, Coding J, Sano K, Millán JL, Terkeltaub R 2000 Tissue-nonspecific alkaline phosphatase (TNALP) and plasma cell membrane glycoprotein-1 (PC-1) act as selective and mutual antagonists of mineralizing activity by murine osteoblasts. Am J Phys Regulat Integrat Physiol 279:R1365-R1377.
15. Hessle L, Johnson KA, Anderson HC, Narisawa S, Sali A, Coding JW, Terkeltaub R, Millán JL 2002 Tissue-nonspecific alkaline phosphatase and plasma cell membrane glycoprotein-1 are central antagonistic regulators of bone mineralization. Proc Natl Acad Sci USA 99:9445-9449.
16. Johnson K, Coding J, Van Etten D, Sali A, Hu SI, Farley D, Krug H, Hessle L, Millán JL, Terkeltaub R 2003 Linked deficiencies in extracellular PP(i) and osteopontin mediate pathologic calcification associated with defective PC-1 and ANK expression. J Bone Miner Res 18:994-1004.
17. -/- mice. J Bone Miner Res 21:1377-1386.
18. Tanimura A, McGregor DH, Anderson HC 1986 Calcification in atherosclerosis. I. Human studies. J Exp Pathol 2:261-273.
19. Tanimura A, McGregor DH, Anderson HC 1986 Calcification in atherosclerosis. II. Animal studies. J Exp Pathol 2:275-297.
20. Hui M, Li SQ, Holmyard D, Cheng P 1997 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 60:467-472.
21. Hui M, Tenenbaum HC 1998 New face of an old enzyme: Alkaline phosphatase may contribute to human tissue aging by inducing tissue hardening and calcification. Anat Rec 253:91-94.
22. Hsu HH, Camacho NP 1999 Isolation of calcifiable vesicles from human atherosclerotic aortas. Atherosclerosis 143:353-362.
23. Shioi A, Nishizawa Y, Jono S, Koyama H, Hosoi M, Morii H 1995 Beta-glycerophosphate accelerates calcification in cultured bovine vascular smooth muscle cells. Arterioscler Thromb Vasc Biol 15:2003-2009.
24. Shioi A, Katagi M, Okuno Y, Mori K, Jono S, Koyama H, Nishizawa Y 2002 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 91:9-16.
25. Mathieu P, Voisine P, Pepin A, Shetty R, Savard N, Dagenais F 2005 Calcification of human valve interstitial cells is dependent on alkaline phosphatase activity. J Heart Valve Dis 14:353-357.
26. Hoylaerts MF, Ding L, Narisawa S, Van Kerckhoven S, Millán JL 2006 Mammalian alkaline phosphatase catalysis requires active site structure stabilization via the N-terminal amino acid microenvironment. Biochemistry 45:9756-9766.
27. Di Mauro S, Manes T, Hessle H, Kozlenkov A, Pizauro JM, Hoylaerts MF, Millán JL 2002 Kinetic characterization of hypophosphatasia mutations with physiological substrates. J Bone Miner Res 17:1383-1391.
28. Kozlenkov A, Hoylaerts MF, Ny T, LeDu MH, Millán JL 2004 Residues determining the binding specificity of uncompetitive inhibitors to tissue-nonspecific alkaline phosphatase. J Bone Miner Res 19:1862-1872.
29. Sali A, Favaloro JM, Terkeltaub R, Coding JW 1999 Germline deletion of the nucleoside triphosphate pyrophosphohydrolase (NTPPPH) plasma cell membrane glycoprotein-1 (PC-1) produces abnormal calcification of periarticular tissues. In: Vanduffel L, Lemmems R (eds.) Ecto-ATPases and Related Ectoenzymes. Shaker Publishing, Maastrich, The Netherlands, pp. 267-282.
30. Wennberg C, Hessle L, Lundberg P, Mauro S, Narisawa S, Lerner UH, Millán JL 2000 Functional characterization of osteoblasts and osteoclasts from alkaline phosphatase knockout mice. J Bone Miner Res 15:1879-1888.
31. Roberts S, Narisawa S, Harmey D, Millán J, Farquharson C 2007 Functional involvement of PHOSPHO1 in matrix vesicle-mediated skeletal calcification. J Bone Miner Res 22:617-627.
32. Hoylaerts MF, Manes T, Millán JL 1992 Molecular mechanism of uncompetitive inhibition of human placental and germ cell alkaline phosphatase. Biochem J 286:23-30.
33. Tintut Y, Patel J, Territo M, Saini T, Parhami F, Demer LL 2002 Monocyte/macrophage regulation of vascular calcification. Circulation 105:650-655.
34. Watson KE, Bostrom K, Ravindranath R, Lam T, Norton B, Demer LL 1994 TGF-beta 1 and 25-hydroxycholesterol stimulate osteoblast-like vascular cells to calcify. J Clin Invest 93:2106-2113.
35. Wada T, McKee MD, Steitz S, Giachelli CM 1999 Calcification of vascular smooth muscle cell cultures: Inhibition by osteopontin. Circ Res 84:166-178.
36. Steitz SA, Speer MY, Curinga G, Yang HY, Haynes P, Aebersold R, Schinke T, Karsenty G, Giachelli CM 2001 Smooth muscle cell phenotypic transition associated with calcification: Upregulation of Cbfa1 and downregulation of smooth muscle lineage markers. Circ Res 89:1147-1154.
37. Tintut Y, Alfonso Z, Saini T, Radcliff K, Watson K, Bostrom K, Demer LL 2003 Multilineage potential of cells from the artery wall. Circulation 108:2505-2510.
38. Hsu HH, Anderson HC 1978 Calcification of isolated matrix vesicles and reconstituted vesicles from fetal bovine cartilage. Proc Natl Acad Sci USA 75:3805-3808.
39. Ali SY, Sajdera SW, Anderson HC 1970 Isolation and characterization of calcifying matrix vesicles from epiphyseal cartilage. Proc Natl Acad Sci USA 67:1513-1520.
40. Kim KM 1976 Calcification of matrix vesicles in human aortic valve and aortic media. Fed Proc 35:156-162.
41. Hsu HHT, Camacho NP, Sun F, Tawik O, Aono H 2000 Isolation of calcifiable vesicles from aortas of rabbits fed with high cholesterol diets. Atherosclerosis 153:337-348.
42. Witte RS, Cnaan A, Mansour EG, Barylak E, Harris JE, Schutt AJ 2001 Comparison of 5-fluorouracil alone, 5-flourouracil with levamisole, and 5-flourouracil with hepatic irradiation in the treatment of patients with residual, nonmeasurable, intraabdominal metastasis after undergoing resection for colorectal carcinoma. Cancer 91:1020-1028.
43. Taal BG, van Tinteren H, Zoetmulder FA, NACCP group 2001 Adjuvant 5FU plus levamisole in colonic or rectal cancer: Improved survival in stage II and III. Br J Cancer 85:1437-1443.
44. Powe TA, Powers RD 1985 Periorchitis after tetramisole treatment in bulls implaned with Setaria labiatopapillos. J Am Vet Med Assoc 186:588-589.
45. Bhopale GM, Bhatnagar BS 1984 Serum protein profile of mice during infection of Ancylostoma caninum and after the administration of tetramisole and levamisole. J Hyg Epidemiol Microbiol Immunol 28:455-459.
46. Eisenberg E, Shklar G 1977 Levamisole and hamster pouch carcinogenesis. Oral Surg Oral Med Oral Path 43:562-571.