Design, synthesis and biological characterization of novel inhibitors of CD38

Organic and Biomolecular Chemistry

Volumn 9, Issue 9, 2011, Pages 3246-3257

  Dong, Min ^a   Si, Yuan Qi ^a   Sun, Shuang Yong ^a   Pu, Xiao Ping ^a   Yang, Zhen Jun ^a   Zhang, Liang Ren ^a   Zhang, Li He ^a   Leung, Fung Ping ^b   Lam, Connie Mo Ching ^b   Kwong, Anna Ka Yee ^b   Yue, Jianbo ^b   Zhou, Yeyun ^c   Kriksunov, Irina A ^c   Hao, Quan ^b   Cheung Lee, Hon ^b  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

^c Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SITE; ADP-RIBOSE; AROMATIC GROUP; BIOLOGICAL CHARACTERIZATION; DRUG DEVELOPMENT; GUINEA PIGS; LYMPHOCYTE ACTIVATION; MULTI-FUNCTIONAL; PHYSIOLOGICAL EFFECTS; PHYSIOLOGICAL FUNCTIONS; RATIONAL DESIGN; SUBSTRATE RECOGNITION;

AMIDES; COMPUTER SIMULATION; ENZYMES; PHYSIOLOGICAL MODELS; PHYSIOLOGY; STRUCTURAL DESIGN;

CRYSTAL STRUCTURE;

CD38 ANTIGEN;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG DESIGN; GUINEA PIG; MALE; PROTEIN DOMAIN; RAT; SYNTHESIS;

ANIMALS; ANTIGENS, CD38; DRUG DESIGN; GUINEA PIGS; MALE; MODELS, MOLECULAR; PROTEIN INTERACTION DOMAINS AND MOTIFS; RATS;

CAVIA; RATTUS;

EID: 79954431421     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00768d     Document Type: Article

References (53)

1. E. L. Reinherz P. C. Kung G. Goldstein R. H. Levey S. F. Schlossman Discrete stages of human intrathymic differentiation: analysis of normal thymocytes and leukemic lymphoblasts of T-cell lineage Proc. Natl. Acad. Sci. U. S. A. 1980 77 1588 1592 (Pubitemid 10073807)
2. H. C. Lee Enzymatic functions and structures of CD38 and homologs. Chem. Immunol. 2000 75 39 59 (Pubitemid 30088768)
3. H. C. Lee Physiological functions of cyclic ADP-ribose and NAADP as calcium messengers Annu. Rev. Pharmacol. 2001 41 317 345 (Pubitemid 32385891)
4. H. C. Lee R. Aarhus D. Levitt The crystal structure of cyclic ADP-ribose Nat. Struct. Biol. 1994 1 143 144
5. 2+- mobilizing activity J. Biol. Chem. 1989 264 1608 15 (Pubitemid 19051000)
6. M. Howard J. C. Grimaldi J. F. Bazan F. E. Lund L. Santos-Argumedo R. M. Parkhouse T. F. Walseth H. C. Lee Formation and hydrolysis of cyclic ADP-ribose catalyzed by lymphocyte antigen CD38 Science 1993 262 1056 1059 (Pubitemid 24035045)
7. i, and insulin secretion J. Biol. Chem. 1999 274 1869 1872
8. S. Partida-Sanchez D. A. Cockayne S. Monard E. L. Jacobson N. Oppenheimer B. Garvy K. Kusser S. Goodrich M. Howard A. Harmsen T. D. Randall F. E. Lund Cyclic ADP-ribose production by CD38 regulates intracellular calcium release, extracellular calcium influx and chemotaxis in neutrophils and is required for bacterial clearance in vivo Nat. Med. 2001 7 1209 1216 (Pubitemid 33063776)
9. G. Shubinsky M. Schlesinger The CD38 lymphocyte differentiation marker: new insight into its ectoenzymatic activity and its role as a signal transducer Immunity 1997 7 315 324 (Pubitemid 27446006)
10. M. Mitsui-Saito I. Kato S. Takasawa H. Okamoto T. Yanagisawa CD38 gene disruption inhibits the contraction induced by alphaadrenoceptor stimulation in mouse aorta J. Vet. Med. Sci. 2003 65 1325 1330 (Pubitemid 41365432)
11. 2+ signaling using CD38 knockout mice J. Biol. Chem. 2001 276 649 655 (Pubitemid 32050361)
12. S. Partida-Sanchez S. Goodrich K. Kusser N. Oppenheimer T. D. Randall F. E. Lund Regulation of dendritic cell trafficking by the ADPribosyl cyclase CD38: impact on the development of humoral immunity Immunity 2004 20 279 291 (Pubitemid 38388230)
13. L. Sun J. Iqbal S. Dolgilevich T. Yuen X. B. Wu B. S. Moonga O. A. Adebanjo P. J. Bevis F. Lund C. L. Huang H. C. Blair M. Zaidi Disordered osteoclast formation and function in a CD38 (ADP-ribosyl cyclase)-deficient mouse establishes an essential role for CD38 in bone resorption FASEB J. 2003 17 369 375 (Pubitemid 36292952)
14. J. D. Johnson E. L. Ford E. Bernal-Mizrachi K. L. Kusser D. S. Luciani Z. Han H. Tran T. D. Randall F. E. Lund K. S. Polonsky Suppressed insulin signaling and increased apoptosis in CD38-null islets Diabetes 2006 55 2737 2746 (Pubitemid 44923672)
15. D. Jin H. X. Liu H. Hirai et al. CD38 is critical for social behaviour by regulating oxytocin secretion Nature 2007 446 41 45 (Pubitemid 46348037)
16. S. Deaglio T. Vaisitti S. Aydin E. Ferrero F. Malavasi In-tandem insight from basic science combined with clinical research: CD38 as both marker and key component of the pathogenetic network underlying chronic lymphocytic leukemia Blood 2006 108 1135 1144 (Pubitemid 44232007)
17. F. Morabito R. N. Damle S. Deaglio M. Keating M. Ferrarini N. Chiorazzi The CD38 ectoenzyme family: advances in basic science and clinical practice Mol. Med. 2006 12 342 344 (Pubitemid 46489830)
18. H. C. Lee Mechanisms of calcium signaling by cyclic ADPribose and NAADP Physiol. Rev. 1997 77 1133 1164 (Pubitemid 27459581)
19. R. Graeff Q. Liu I. A. Kriksunov Q. Hao H. C. Lee Acidic residues at the active sites of CD38 and ADP-ribosyl cyclase determine nicotinic acid adenine dinucleotide phosphate (NAADP) synthesis and hydrolysis activities J. Biol. Chem. 2006 281 28951 28957 (Pubitemid 44507038)
20. J. T. Slama A. M. Simmons Carbanicotinamide adenine dinucleotide: synthesis and enzymological properties of a carbocyclic analogue of oxidized nicotinamide adenine dinucleotide Biochemistry 1988 271 183 193
21. + glycohydrolase activity of CD38 by carbocyclic NAD analogues Biochem. J. 1998 335 631 636 (Pubitemid 28515417)
22. + Glycohydrolase by Arabino Analogues of α-NAD J. Biol. Chem. 1992 267 9606 9611
23. A. A. Sauve H. T. Deng R. H. Angeletti V. L. A Schramm Covalent Intermediate in CD38 Is Responsible for ADP-Ribosylation and Cyclization Reactions J. Am. Chem. Soc. 2000 122 7855 7859 (Pubitemid 30659405)
24. Q. Liu R. Graeff I. A. Kriksunov et al. Structural basis for enzymatic evolution from a dedicated ADP-ribosyl cyclase to a multi-functional NAD hydrolase J. Biol. Chem. 2009 284 27637 27645
25. Q. Liu I. A. Kriksunov H. Jiang R. Graeff H. Lin H. C. Lee Hao Q. Covalent, and noncovalent intermediates of an NAD utilizing enzyme, human CD38 Chem. Biol. 2008 15 1068 1078
26. A. A. Sauve V. L. Schramm Mechanism-Based, Inhibitors of CD38: A Mammalian Cyclic ADP-Ribose Synthetase Biochemistry 2002 41 8455 8463 (Pubitemid 34705500)
27. Q. Liu I. A. Kriksunov R. Graeff et al. Crystal structure of human CD38 extracellular domain Structure 2005 13 1331 1339 (Pubitemid 41262100)
28. Q. Liu I. A Kriksunov R. Graeff C. Munshi H. C. Lee Q. Hao Structural basis for the mechanistic understanding of human CD38-controlled multiple catalysis J. Biol. Chem. 2006 281 32861 32869 (Pubitemid 46036841)
29. Q. Liu I. A. Kriksunov C. Moreau R. Graeff B. V. Potter H C. Lee Q. Hao Catalysis-associated conformational changes revealed by human CD38 complexed with a non-hydrolyzable substrate analog J. Biol. Chem. 2007 282 24825 24832 (Pubitemid 47347511)
30. 13C NMR characterization of hemiamidal isoniazid-NAD(H) adducts as possible inhibitors of InhA reductase of mycobacterium tuberculosis Chem.-Eur. J. 2003 9 2034 2038
31. J. Pernak J. Kalewska H. Ksycinska J. Cybulski Synthesis and anti-microbial activities od some pyridinium salts with alkoxymethyl hydrophobic group Eur. J. Med. Chem. 2001 36 899 907 (Pubitemid 34036541)
32. S. Saluja R. Zou J. C. Drach L. B. Townsend Structure-Activity Relationships among 2-Substituted 5,6-Dichloro-,4,6-Dichloro-,and 4,5-Dichloro-1-[(2- hydroxyethoxy)methyl]-and-1-[(1,3-dihydroxy-2-propoxy) methyl] benzimidazoles J. Med. Chem. 1996 39 881 891
33. +-affinity Heterocycles 2001 54 123 130 (Pubitemid 32162724)
34. 2 linker and their reactivation potency for organophosphorus agents-inhibited acetylcholinesterase Bioorg. Med. Chem. 2007 15 7704 7710 (Pubitemid 47575918)
35. M. Y. Jang S. De. Jonghe L. J. Gao P. Herdewijn Regioselective cross-coupling reactions and nucleophilic aromatic substitutions on a 5,7-dichloropyrido[4,3-d]pyrimidine scaffold Tetrahedron Lett. 2006 47 8917 8920 (Pubitemid 44693613)
36. R. Graeff H. C. Lee A novel cycling assay for cellular cADP-ribose with nanomolar sensitivity Biochem J. 2002 361 379 384 (Pubitemid 34174505)
37. 2+ Release by M1 muscarinic receptor activation in coronary arterial smooth muscle J. Vasc. Res. 2003 40 28 36 (Pubitemid 36351193)
38. 2+-pathway promotes cell proliferation and delays NGF-induced differentiation in PC12 cells J. Biol. Chem. 2009 284 29335 29242
39. A. Deepak T. A. Deshpande S. D. White, et al. CD38/cyclic ADP-ribose signaling: role in the regulation of calcium homeostasis in airway smooth muscle Am. J. Physiol.: Lung Cell. Mol. Phys. 2005 288 773 788
40. G. T. Stevenson CD38 as a therapeutic target Mol. Med. 2006 12 345 346 (Pubitemid 46489831)
41. E. Naylor A. Arredouani S. R. Vasudevan A. M. Lewis R. Parkesh A. Mizote D. Rosen J. M. Thomas M. Izumi A Ganesan A Galione G. C. Churchill Identification of a chemical probe for NAADP by virtual screening Nat. Chem. Biol. 2009 5 220 226
42. H. C. Lee C. B. Munshi Large scale production of human CD38 in yeast by fermentation Methods Enzymol. 1997 280 230 241
43. 2+ entry blockers on airway constriction induced by muscarinic receptor stimulation Br. J. Anaesth. 2003 90 671 675 (Pubitemid 36592343)
44. Z. Otwinowski W. Minor Processing of X-ray Diffraction Data Collected in Oscillation Mode Methods Enzymol. 1997 276 307 326 (Pubitemid 27085611)
45. Acta Crystallogr., Sect. D: Biol. Crystallogr., 1994, D50, pp. 760-763
46. G. M. Morris D. S. Goodsell R. S. Halliday R. Huey W. E. Hart R. K. Belew A. J. Olson Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function J. Comput. Chem. 1998 19 1639 1662 (Pubitemid 128590223)
47. A. W. Schuettelkopf D. M. F. van. Aalten PRODRG-a tool for high-throughput crystallography of protein-ligand complexes Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004 D60 1355 1363 (Pubitemid 41079731)
48. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., Gaussian, Inc., Pittsburgh PA, 2003
49. E. Lindahl B. Hess D. von der Spoel Gromacs 3.0: A package for molecular simulation and trajectory analysis J. Mol. Mod. 2001 7 306 317 (Pubitemid 36153547)
50. W. F. van Gunsteren, S. R. Billeter, A. A. Eising, P. H. Hunenberger, P. Kruger, A. E. Mark, W. R. P. Scott, I. G. Tironi, Biomolecular Simulation: The GROMOS96 manual and user guide. Zurich, Switzerland: Hochschulverlag AG an der ETH Zürich. 1996
51. B. Hess H. Bekker H. J. C. Berendsen J. G. E. M. Fraaije LINCS: A linear constraint solver for molecular simulations J. Comput. Chem. 1997 18 1463 1472 (Pubitemid 127637344)
52. T. Darden D. York L. Pedersen Particle mesh Ewald: An N-log(N) method for Ewald sums in large systems J. Chem. Phys. 1993 98 10089 10092
53. H. J. C. Berendsen J. P. M. Postma W. F. van Gunsteren A. Dinola J. R. Haak Molecular dynamics with coupling to an external bath J. Chem. Phys. 1984 81 3684 3690