Development of a dimethylarginine dimethylaminohydrolase (DDAH) assay for high-throughput chemical screening

Journal of Biomolecular Screening

Volumn 17, Issue 5, 2012, Pages 651-661

  Ghebremariam, Yohannes T ^a   Erlanson, Daniel A ^a   Yamada, Keisuke ^a   Cooke, John P ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

asymmetric dimethylarginine; diabetes; hypertension; idiopathic pulmonary fibrosis; nitric oxide

Indexed keywords

4 CHLOROMERCURIBENZOIC ACID; 4 MERCAPTO 5 METHOXY 2 PHENYL 3(2H) PYRIDAZINONE; ACETYLSALICYLIC ACID; ARGININE; CITRULLINE; CLOPIDOGREL; COMPOUND 2548 0703; COMPOUND 2548 0707; DIMETHYLARGININASE; DIMETHYLARGININASE INHIBITOR; EBSELEN; ENZYME INHIBITOR; GLUTATHIONE TRANSFERASE; N (2,3 DIPHENYL 1,2,4 THIADIAZOL 5(2H) YLIDENE)METHANAMINE; N(G),N(G) DIMETHYLARGININE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; PHENYLMERCURIC ACETATE; RECOMBINANT ENZYME; UNCLASSIFIED DRUG;

ARTICLE; CARDIOVASCULAR DISEASE; CHEMICAL STRUCTURE; DIABETES MELLITUS; ENZYME ACTIVITY; ENZYME ASSAY; FIBROSING ALVEOLITIS; HIGH THROUGHPUT SCREENING; HUMAN; HYPERTENSION; LUNG FIBROSIS; MASS SPECTROMETRY; MIGRAINE; NEOPLASM; NONHUMAN; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL; PROTEIN PURIFICATION; SEPSIS; WESTERN BLOTTING;

AMIDOHYDROLASES; CELLS, CULTURED; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DISCOVERY; ENZYME ASSAYS; ENZYME INHIBITORS; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; INHIBITORY CONCENTRATION 50; RECOMBINANT PROTEINS; REPRODUCIBILITY OF RESULTS; SMALL MOLECULE LIBRARIES;

EID: 84861825417     PISSN: 10870571     EISSN: 1552454X     Source Type: Journal    
DOI: 10.1177/1087057112441521     Document Type: Article

References (30)

1. Vallance P., Leone A., Calver A., Collier J., Moncada S.. Accumulation of an Endogenous Inhibitor of Nitric Oxide Synthesis in Chronic Renal Failure. Lancet. 1992 ; 339: 572-575
2. Krause C. D., Yang Z. H., Kim Y. S., Lee J. H., Cook J. R., Pestka S.. Protein Arginine Methyltransferases: Evolution and Assessment of Their Pharmacological and Therapeutic Potential. Pharmacol. Ther. 2007 ; 113: 50-87
3. Cooke J. P.. Does ADMA Cause Endothelial Dysfunction?. Arterioscler. Thromb. Vasc. Biol. 2000 ; 20: 2032-2037
4. Cooke J. P.. Asymmetrical Dimethylarginine: The Uber Marker?. Circulation. 2004 ; 109: 1813-1818
5. Palm F., Onozato M. L., Luo Z., Wilcox C. S.. Dimethylarginine Dimethylaminohydrolase (DDAH): Expression, Regulation, and Function in the Cardiovascular and Renal Systems. Am. J. Physiol. Heart Circ. Physiol. 2007 ; 293: H3227 - H3245
6. Leiper J. M., Santa Maria J., Chubb A., MacAllister R. J., Charles I. G., Whitley G. S., Vallance P.. Identification of Two Human Dimethylarginine Dimethylaminohydrolases with Distinct Tissue Distributions and Homology with Microbial Arginine Deiminases. Biochem. J. 1999 ; 343 (Pt 1). 209-214
7. Ogawa T., Kimoto M., Sasaoka K.. Occurrence of a New Enzyme Catalyzing the Direct Conversion of NG,NG-Dimethyl-L-Arginine to L-Citrulline in Rats. Biochem. Biophys. Res. Commun. 1987 ; 148: 671-677
8. Hu X., Atzler D., Xu X., Zhang P., Guo H., Lu Z., Fassett J., Schwedhelm E., Boger R. H., Bache R. J., Chen Y.. Global Dimethylarginine Dimethylaminohydrolase-1 (DDA H1) Gene-Deficient Mice Reveal That DDAH1 Is the Critical Enzyme for Degrading the Cardiovascular Risk Factor Asymmetrical Dimethylarginine. Arterioscler. Thromb. Vasc. Biol. 2011 ; 15: 1540-1546
9. Stuhlinger M. C., Tsao P. S., Her J. H., Kimoto M., Balint R. F., Cooke J. P.. Homocysteine Impairs the Nitric Oxide Synthase Pathway: Role of Asymmetric Dimethylarginine. Circulation. 2001 ; 104: 2569-2575
10. Leiper J., Nandi M.. The Therapeutic Potential of Targeting Endogenous Inhibitors of Nitric Oxide Synthesis. Nat. Rev. Drug Discov. 2011 ; 10: 277-291
11. Chobanyan-Jurgens K., Pham V. V., Stichtenoth D. O., Tsikas D.. Elevated Dimethylarginine Dimethylaminohydrolase (DDAH) Activity in Rheumatoid Arthritis and Spondyloarthritis. Nitric Oxide. 2011 ; 25: 436-438
12. Pullamsetti S. S., Savai R., Dumitrascu R., Dahal B. K., Wilhelm J., Konigshoff M., Zakrzewicz D., Ghofrani H. A., Weissmann N., Eickelberg O., et al. The role of dimethylarginine dimethylaminohydrolase in idiopathic pulmonary fibrosis. Sci. Transl. Med. 2011 ; 3 :
13. Johnson C. M., Monzingo A. F., Ke Z., Yoon D. W., Linsky T. W., Guo H., Robertus J. D., Fast W.. On the Mechanism of Dimethylarginine Dimethylaminohydrolase Inactivation by 4-Halopyridines. J. Am. Chem. Soc. 2011 ; 133: 10951-10959
14. Linsky T., Wang Y., Fast W.. Screening for Dimethylarginine Dimethylaminohydrolase Inhibitors Reveals Ebselen as a Bioavailable Inactivator. ACS Med. Chem. Lett. 2011 ; 2: 592-596
15. Lluis M., Wang Y., Monzingo A. F., Fast W., Robertus J. D.. Characterization of C-Alkyl Amidines as Bioavailable Covalent Reversible Inhibitors of Human DDAH-1. ChemMedChem. 2011 ; 6: 81-88
16. Wang Y., Monzingo A. F., Hu S., Schaller T. H., Robertus J. D., Fast W.. Developing Dual and Specific Inhibitors of Dimethylarginine Dimethylaminohydrolase-1 and Nitric Oxide Synthase: Toward a Targeted Polypharmacology to Control Nitric Oxide. Biochemistry. 2009 ; 48: 8624-8635
17. Kotthaus J., Schade D., Muschick N., Beitz E., Clement B.. Structure-Activity Relationship of Novel and Known Inhibitors of Human Dimethylarginine Dimethylaminohydrolase-1: Alkenyl-Amidines as New Leads. Bioorg. Med. Chem. 2008 ; 16: 10205-10209
18. Linsky T., Fast W.. A Continuous, Fluorescent, High-Throughput Assay for Human Dimethylarginine Dimethylaminohydrolase-1. J. Biomol. Screen. 2011 ; 16: 1089-1097
19. Johnson C. M., Linsky T. W., Yoon D. W., Person M. D., Fast W.. Discovery of Halopyridines as Quiescent Affinity Labels: Inactivation of Dimethylarginine Dimethylaminohydrolase. J. Am. Chem. Soc. 2011 ; 133: 1553-1562
20. Leiper J., Nandi M., Torondel B., Murray-Rust J., Malaki M., O'Hara B., Rossiter S., Anthony S., Madhani M., Selwood D., et al. Disruption of Methylarginine Metabolism Impairs Vascular Homeostasis. Nat. Med. 2007 ; 13: 198-203
21. 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., et al. Discovery of Inhibitors of the Pentein Superfamily Protein Dimethylarginine Dimethylaminohydrolase (DDAH), by Virtual Screening and Hit Analysis. Bioorg. Med. Chem. Lett. 2007 ; 17: 3953-3956
22. Prescott L. M., Jones M. E.. Modified Methods for the Determination of Carbamyl Aspartate. Anal. Biochem. 1969 ; 32: 408-419
23. Zhang J. H., Chung T. D., Oldenburg K. R.. A Simple Statistical Parameter for Use in Evaluation and Validation of High Throughput Screening Assays. J. Biomol. Screen. 1999 ; 4: 67-73
24. Knipp M., Charnock J. M., Garner C. D., Vasak M.. Structural and Functional Characterization of the Zn(II) Site in Dimethylargininase-1 (DDAH-1) from Bovine Brain: Zn(II) Release Activates DDAH-1. J. Biol. Chem. 2001 ; 276: 40449-40456
25. Knipp M., Vasak M.. A Colorimetric 96-Well Microtiter Plate Assay for the Determination of Enzymatically Formed Citrulline. Anal. Biochem. 2000 ; 286: 257-264
26. Baell J. B., Holloway G. A.. New Substructure Filters for Removal of Pan Assay Interference Compounds (PAINS) from Screening Libraries and for Their Exclusion in Bioassays. J. Med. Chem. 2010 ; 53: 2719-2740
27. Bloomgarden Z. T.. Insulin Resistance, Dyslipidemia, and Cardiovascular Disease. Diabetes Care. 2007 ; 30: 2164-2170
28. Kielstein J. T., Donnerstag F., Gasper S., Menne J., Kielstein A., Martens-Lobenhoffer J., Scalera F., Cooke J. P., Fliser D., Bode-Boger S. M.. ADMA Increases Arterial Stiffness and Decreases Cerebral Blood Flow in Humans. Stroke. 2006 ; 37: 2024-2029
29. Guterman L.. Covalent Drugs Form Long-Lived Ties. Chem. Eng. News. 2011 ; 89: 19-26
30. Nakamura Y., Feng Q., Kumagai T., Torikai K., Ohigashi H., Osawa T., Noguchi N., Niki E., Uchida K.. Ebselen, a Glutathione Peroxidase Mimetic Seleno-Organic Compound, as a Multifunctional Antioxidant: Implication for Inflammation-Associated Carcinogenesis. J. Biol. Chem. 2002 ; 277: 2687-2694