1,3-disubstituted-4-aminopyrazolo [3, 4-d] pyrimidines, a new class of potent inhibitors for phospholipase D

Chemical Biology and Drug Design

Volumn 84, Issue 3, 2014, Pages 270-281

  Kulkarni, Aditya ^a   Quang, Phong ^b   Curry, Victoriana ^b   Keyes, Renee ^b   Zhou, Weihong ^a   Cho, Hyejin ^a   Baffoe, Jonathan ^a   Török, Béla ^a   Stieglitz, Kimberly ^b  

^a UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

^b Roxbury Community College   (United States)

Author keywords

chemical biology; drug design; protease and ligands (substrate inhibitor)

Indexed keywords

ENZYME INHIBITOR; MICELLE; PHOSPHOLIPASE D; PHOSPHOLIPASE D1; PHOSPHOLIPASE D2; PROTEIN BINDING; PYRAZOLE DERIVATIVE; PYRAZOLO(3,4-D)PYRIMIDINE; PYRIMIDINE DERIVATIVE;

ANTAGONISTS AND INHIBITORS; BINDING SITE; BIOSYNTHESIS; CHEMISTRY; DRUG DESIGN; ENZYME ACTIVE SITE; GENETICS; HEK293 CELL LINE; HUMAN; KINETICS; METABOLISM; MICELLE; MOLECULAR DYNAMICS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

BINDING SITES; CATALYTIC DOMAIN; DRUG DESIGN; ENZYME INHIBITORS; HEK293 CELLS; HUMANS; KINETICS; MICELLES; MOLECULAR DYNAMICS SIMULATION; PHOSPHOLIPASE D; PROTEIN BINDING; PYRAZOLES; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84905913883     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12319     Document Type: Article

References (29)

1. Brown H.A., Henage L.G., Preininger A.M., Xiang Y., Exton J.H., (2007) Biochemical analysis of phospholipase D. Methods Enzymol; 434: 49-87.
2. Foster D.A., (2009) Phosphatidic acid signalling to mTOR: signals for the survival of human cancer cells. Biochim Biophys Acta; 1791: 949-955.
3. Zhao Y., Ehara H., Akao Y., Shamoto M., Nakagawa Y., Banno Y., Deguchi T., Ohishi N., Yagi K., Nozawa Y., (2000) Increased activity and intranuclear expression of phospholipase D2 in human renal cancer. Biochem Biophys Res Commun; 278: 140-143.
4. Uchida N., Okamura S., Kuwano H., (1999) Phospholipase D activity in human gastric carcinoma. Anticancer Res; 19: 671-676.
5. Yamada Y., Hamajima N., Kato T., Iwata H., Yamamura Y., Shinoda M., Suyama M., Mitsudomi T., Tajima K., Kusakabe S., Yoshida H., Banno Y., Akao Y., Tanaka M., Nozawa Y., (2003) Association of a polymorphism of the phospholipase D(2) gene with the prevalence of colorectal cancer. J Mol Med; 81: 126-131.
6. Scott S.A., Selvy P.E., Buck J.R., Cho H.P., Criswell T.L., Thomas A.L., Armstrong M.D., Arteaga C.L., Lindsley C.W., Brown H.A., (2009) Design of isoform-selective phospholipase D inhibitors that modulate cancer cell invasiveness. Nat Chem Biol; 5: 108-117.
7. Jin J.K., Ahn B.H., Na Y.J., Kim J.I., Kim Y.S., Choi E.K., Ko Y.G., Chung K.C., Kozlowski P.B., Mindo S., (2007) Phospholipase D1 is associated with amyloid precursor protein in Alzheimer's disease. Neurobiol Aging; 28: 1015-1027.
8. Oliveira T.G., Di Paolo G., (2010) Phospholipase D in brain function and Alzheimer's disease. Biochim Biophys Acta; 1801: 799-805.
9. Lewis J.A., Scott S.A., Lavieri R., Buck J.R., Selvy P.E., Stoops S.L., Armstrong M.D., Brown H.A., Lindsley C.W., (2009) Design and synthesis of isoform-selective phospholipase D (PLD) inhibitors. Part I: impact of alternative halogenated privileged structures for PLD1 specificity. Bioorg Med Chem Lett; 19: 1916-1920.
10. Lavieri R., Scott S.A., Lewis J.A., Selvy P.E., Armstrong M.D., Brown H.A., Lindsley C.W., (2009) Design and synthesis of isoform-selective phospholipase D (PLD) inhibitors. Part II: identification of the 1, 3, 8-triazaspiro[4,5]decan-4-one privileged structure that engenders PLD2 selectivity. Bioorg Med Chem Lett; 19: 2240-2243.
11. Leiros I., Mcsweeney S., Hough E., (2004) The reaction mechanism of phospholipase D from Streptomyces sp strain PMF. Snapshots along the reaction pathway reveal a pentacoordinate reaction intermediate and an unexpected final product. J Mol Biol; 339: 805-820.
12. Bishop A.C., Kung C., Shah K., Witucki L., Shokat K.M., Liu Y., (1999) Generation of onospecific nanomolar tyrosine kinase inhibitors via a chemical genetic approach. J Am Chem Soc; 121: 627-631.
13. Apsel B., Blair J.A., Gonzalez B., Nazif T.M., Feldman M.E., Aizenstein B., Hoffman R., Williams R.L., Shokat K.M., Knight Z.A., (2008) Targeted polypharmacology: discovery of dual inhibitors of tyrosine and phosphoinositide kinases. Nat Chem Biol; 4: 691-699.
14. Hanefeld U., Rees C.W., White J.P., Williams D.J., (1996) One-pot synthesis of tetrasubstituted pyrazoles-proof of regiochemistry. J Chem Soc Perkin Trans; 1: 1545-1552.
15. Geng D., Baker D.P., Foley S.F., Zhou C., Stieglitz K., Roberts M.F., (1999) A 20-kDa domain is required for phosphatidic acid-induced allosteric activation of phospholipase D from Streptomyces chromofuscus. Biochim Biophys Acta; 1430: 234-244.
16. Stieglitz K., Seaton B., Roberts M.F., (1999) The role of interfacial binding in the activation of Streptomyces chromofuscus phospholipase D by phosphatidic acid. J Biol Chem; 274: 35367-35374.
17. Stieglitz K.A., Seaton B., Roberts M.F., (2001) Binding of proteolytically processed phospholipase D from Streptomyces chromofuscus to phosphatidylcholine membranes facilitates vesicle aggregation and fusion. Biochemistry; 40: 13954-13963.
18. Su W., Yeku O., Olepu S., Genna A., Park J.S., Ren H., Du G., Gelb M.H., Morris A.J., Frohman M.A., (2009) 5-Fluoro-2-indolyl des-chlorohalopemide (FIPI), a phospholipase D pharmacological inhibitor that alters cell spreading and inhibits chemotaxis. Mol Pharmacol; 75: 437-446.
19. 2+ interaction, or an allosteric effect? J Biol Chem; 273: 12195-12202.
20. Yang H., Roberts M.F., (2003) Phosphohydrolase and transphosphatidylation reactions of two Streptomyces phospholipase D enzymes: covalent versus non-covalent catalysis. Protein Sci; 12: 2087-2098.
21. Hammond S.M., Altshuller Y.M., Sung T.C., Rudge S.A., Rose K., Engebrecht J., Morris A.J., Frohman M.A., (1995) Human ADP-ribosylation factor-activated phosphati- dylcholine-specific phospholipase D defines a new and highly conserved gene family. J Biol Chem; 270: 29640-29643.
22. Su W., Chardin P., Yamazaki M., Kanaho Y., Du RhoA-mediated G., (2006) Phospholipase D1 signaling is not required for the formation of stress fibers and focal adhesions. Cell Signal; 18: 469-478.
23. Du G., Huang P., Liang B.T., Frohman M.A., MA, (2004) Phospholipase D2 localizes to the plasma membrane and regulates angiotensin II receptor endocytosis. Mol Biol Cell; 15: 1024-1030.
24. Morris A.J., Frohman M.A., Engebrecht J., (1997) Measurement of phospholipase D activity. Anal Biochem; 252: 1-9.
25. Zeniou-Meyer M., Zabari N., Ashery U., Chasserot-Golaz S., Haeberle A.M., Demais V., Bailly Y., Gottfried I., Nakanishi H., Neiman A.M., Du G., Frohman M.A., Bader M.F., Vitale N., (2007) Phospholipase D1 production of phosphatidic acid at the plasma membrane promotes exocytosis of large dense-core granules at a late stage. J Biol Chem; 282: 21746-21757.
26. Kang J.H., Chung J.K., (2008) Molecular-genetic imaging based on reporter gene expression. J Nucl Med; 49: 164S-179S.
27. Jung A.C., Criqui M.C., Rutschmann S., Hoffmann J.A., Ferrndon D., (2001) Microfluorometer assay to measure the expression of beta-galactosidase and green fluorescent reporter genes in single Drosophila files. Biotechniques; 30: 594-598, 600-1.
28. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., Olsen A.J.J., (1998) Automated docking using a Lamarckian genetic algorithm and empirical binding free energy function. Comput Chem; 19: 1639-1662.
29. Schüttelkopf A.W., van Aalten D.M.F., (2004) A tool for high-throughput crystallography of protein-ligand complexes. Acta Crystallogr D Biol Crystallogr; D60: 1355-1363.