Structure-activity relationship of novel and known inhibitors of human dimethylarginine dimethylaminohydrolase-1: Alkenyl-amidines as new leads

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 24, 2008, Pages 10205-10209

  Kotthaus, Jürke ^a   Schade, Dennis ^a   Muschick, Nikola ^a   Beitz, Eric ^a   Clement, Bernd ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

ADMA; Dimethylarginine dimethylaminohydrolase (DDAH); Inhibitor; N alkyl l arginines; Nitric oxide (NO); Vinyl l NIO

Indexed keywords

ALKENYL GROUP; AMIDINE; ARGININE DERIVATIVE; BENZENE DERIVATIVE; DIMETHYLARGININASE; DIMETHYLARGININE DIMETHYLAMINOHYDROLASE 1; DIMETHYLARGININE DIMETHYLAMINOHYDROLASE 1 INHIBITOR; FLUORINE DERIVATIVE; GUANIDINE; INDOLE DERIVATIVE; N 5 (1 IMINO BUT 3 ENYL)ORNITHINE; N OMEGA (2 METHOXYETHYL)ARGININE; NITRIC OXIDE SYNTHASE; ORNITHINE DERIVATIVE; SR 445; SULFONIC ACID DERIVATIVE; THIOBARBITURIC ACID DERIVATIVE; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG BINDING SITE; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; ENZYME ACTIVE SITE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IC 50; STRUCTURE ACTIVITY RELATION;

AMIDINES; AMIDOHYDROLASES; ARGININE; HUMANS; INHIBITORY CONCENTRATION 50; KINETICS; NITRIC OXIDE; NITRIC OXIDE DONORS; NITRIC OXIDE SYNTHASE TYPE II; STRUCTURE-ACTIVITY RELATIONSHIP;

RATTUS;

EID: 56349085708     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.10.058     Document Type: Article

References (44)

1. Ignarro L., and Murad F.e. Advances in Pharmacology (1995), Academic Press, San Diego
2. Alderton W.K., Cooper C.E., and Knowles R.G. Biochem. J. 357 (2001) 593
3. Vallance P., and Leiper J. Nat. Rev. 1 (2002) 939
4. Ferroni P., Basili S., Paoletti V., and Davi G. Nutr. Metab. Cardiovasc. Dis. 16 (2006) 222
5. Raij L. J. Clin. Hypertens. (Greenwich) 8 (2006) 30
6. Toda N., Ayajiki K., and Okamura T. Pharmacol. Ther. 106 (2005) 233
7. Neeb L., and Reuter U. CNS Neurol. Disord. Drug Targets 6 (2007) 258
8. Knipp M. Chembiochem 7 (2006) 879
9. Ogawa T., Kimoto M., and Sasaoka K. J. Biol. Chem. 264 (1989) 10205
10. Tran C.T., Fox M.F., Vallance P., and Leiper J.M. Genomics 68 (2000) 101
11. Anthony S., Leiper J., and Vallance P. Vasc. Med. 10 Suppl. 1 (2005) S3
12. Boucher J.L., Custot J., Vadon S., Delaforge M., Lepoivre M., Tenu J.P., Yapo A., and Mansuy D. Biochem. Biophys. Res. Commun. 203 (1994) 1614
13. Clement B., Kunze T., and Heberling S. Biochem. Biophys. Res. Commun. 349 (2006) 869
14. Boucher J.L., Genet A., Vadon S., Delaforge M., Henry Y., and Mansuy D. Biochem. Biophys. Res. Commun. 187 (1992) 880
15. Boger R.H. Ann. Med. 38 (2006) 126
16. Leiper J., and Vallance P. Cardiovasc. Res. 43 (1999) 542
17. Cooke J.P. Arterioscler. Thromb. Vasc. Biol. 20 (2000) 2032
18. Abe T., Tohgi H., Murata T., Isobe C., and Sato C. Neurosci. Lett. 312 (2001) 177
19. MacAllister R.J., Parry H., Kimoto M., Ogawa T., Russell R.J., Hodson H., Whitley G.S., and Vallance P. Br. J. Pharmacol. 119 (1996) 1533
20. Rossiter S., Smith C.L., Malaki M., Nandi M., Gill H., Leiper J.M., Vallance P., and Selwood D.L. J. Med. Chem. 48 (2005) 4670
21. Leiper J., Nandi M., Torondel B., Murray-Rust J., Malaki M., O'Hara B., Rossiter S., Anthony S., Madhani M., Selwood D., Smith C., Wojciak-Stothard B., Rudiger A., Stidwill R., McDonald N.Q., and Vallance P. Nat. Med. 13 (2007) 198
22. Murray-Rust J., Leiper J., McAlister M., Phelan J., Tilley S., Santa Maria J., Vallance P., and McDonald N. Nat. Struct. Biol. 8 (2001) 679
23. Frey D., Braun O., Briand C., Vasak M., and Grutter M.G. Structure 14 (2006) 901
24. Vallance P., Bush H.D., Mok B.J., Hurtado-Guerrero R., Gill H., Rossiter S., Wilden J.D., and Caddick S. Chem. Commun. (Cambridge, England) (2005) 5563
25. Stone E.M., Schaller T.H., Bianchi H., Person M.D., and Fast W. Biochemistry 44 (2005) 13744
26. Knipp M., Braun O., and Vasak M. J. Am. Chem. Soc. 127 (2005) 2372
27. Forbes S.P., Druhan L.J., Guzman J.E., Parinandi N., Zhang L., Green-Church K.B., and Cardounel A.J. Biochemistry 47 (2008) 1819
28. Hartzoulakis B., Rossiter S., Gill H., O'Hara B., Steinke E., Gane P.J., Hurtado-Guerrero R., Leiper J.M., Vallance P., Rust J.M., and Selwood D.L. Bioorg. Med. Chem. Lett. 17 (2007) 3953
29. Kotthaus J., Schade D., Topker-Lehmann K., Beitz E., and Clement B. Bioorg. Med. Chem. 16 (2008) 2305
30. Garvey E.P., Oplinger J.A., Tanoury G.J., Sherman P.A., Fowler M., Marshall S., Harmon M.F., Paith J.E., and Furfine E.S. J. Biol. Chem. 269 (1994) 26669
31. Garvey E.P., Oplinger J.A., Furfine E.S., Kiff R.J., Laszlo F., Whittle B.J., and Knowles R.G. J. Biol. Chem. 272 (1997) 4959
32. Stone E.M., Person M.D., Costello N.J., and Fast W. Biochemistry 44 (2005) 7069
33. Babu B.R., and Griffith O.W. J. Biol. Chem. 273 (1998) 8882
34. Bretscher L.E., Li H., Poulos T.L., and Griffith O.W. J. Biol. Chem. 278 (2003) 46789
35. Zhang H.Q., Fast W., Marletta M.A., Martasek P., and Silverman R.B. J. Med. Chem. 40 (1997) 3869
36. Olken N.M., and Marletta M.A. J. Med. Chem. 35 (1992) 1137
37. Fast W., Levsky M.E., Marletta M.A., and Silverman R.B. Bioorg. Med. Chem. 5 (1997) 1601
38. Reif D.W., and McCreedy S.A. Arch. Biochem. Biophys. 320 (1995) 170
39. Li H., and Poulos T.L. J. Inorg. Biochem. 99 (2005) 293
40. Clement B. Drug Metab. Rev. 34 (2002) 565
41. Schade D., Kotthaus J., and Clement B. Synthesis 15 (2008) 2391
42. Knipp M., and Vasak M. Anal. Biochem. 286 (2000) 257
43. Hevel J.M., and Marletta M.A. Methods Enzymol. 233 (1994) 250
44. Schulz K., Kerber S., and Kelm M. Nitric Oxide 3 (1999) 225