Inhibitors of membranous adenylyl cyclases

Trends in Pharmacological Sciences

Volumn 33, Issue 2, 2012, Pages 64-78

  Seifert, Roland ^a   Lushington, Gerald H ^b   Mou, Tung Chung ^c   Gille, Andreas ^d   Sprang, Stephen R ^c  

^a HANNOVER MEDICAL SCHOOL   (Germany)

^b UNIVERSITY OF KANSAS   (United States)

^c UNIVERSITY OF MONTANA   (United States)

^d CSL LIMITED   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 7 (2 FURANYL) 7,8 DIHYDRO 5(6H) QUINAZOLINE; 2',5' DIDEOXYADENINE; 2',5' DIDEOXYADENOSINE; 3 (6 AMINOPURIN 9 YL)CYCLOPENTANECARBOXYLIC ACID HYDROXYAMIDE; 4 [(1 ANTHRACEN 9 YL METH YLIDENE)AMINO] 2 HYDROXYBENZOIC ACID; 9 (CYCLOPENTYL)ADENINE; 9 (TETRAHYDRO 2 FURYL)ADENINE; 9 (TETRAHYDROFURYL)ADENINE; ADENINE DERIVATIVE; ADENYLATE CYCLASE; ADENYLATE CYCLASE 1; ADENYLATE CYCLASE 2; ADENYLATE CYCLASE INHIBITOR; BENZENE DERIVATIVE; BENZOIC ACID DERIVATIVE; BIPHENYL DERIVATIVE; CALMIDAZOLIUM; CARBOXYLIC ACID DERIVATIVE; DITERPENE; FORSKOLIN DERIVATIVE; G PROTEIN COUPLED RECEPTOR; MESSENGER RNA; N (2 PHENYLCYCLOPENTYL)AZACYCLOTRIDECAN 2 IMINE; NUCLEOTIDE; PROTEIN KINASE; PURINE; PYRIMIDINE; TRYPHOSTIN A25; UNCLASSIFIED DRUG; UNINDEXED DRUG; VIDARABINE;

ALLOSTERISM; ARTERIOSCLEROSIS; BINDING AFFINITY; CIRCADIAN RHYTHM; CONGESTIVE HEART FAILURE; DIABETIC RETINOPATHY; DIARRHEA; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG TARGETING; ENZYME ACTIVE SITE; ENZYME INHIBITION; GENE INACTIVATION; GRAFT REJECTION; HEART DISEASE; HUMAN; HYDROPHOBICITY; MALIGNANT NEOPLASTIC DISEASE; MEDICAL LITERATURE; NEUROPROTECTION; NONHUMAN; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN EXPRESSION; PSORIASIS; REVIEW; SENESCENCE; SKIN INJURY; STRUCTURE ACTIVITY RELATION; WOUND HEALING;

ADENYLATE CYCLASE; AMINO ACID SEQUENCE; ANIMALS; CATALYTIC DOMAIN; HUMANS; MOLECULAR SEQUENCE DATA; NUCLEOTIDES; PROTEIN ISOFORMS;

EID: 84856531711     PISSN: 01656147     EISSN: 18733735     Source Type: Journal    
DOI: 10.1016/j.tips.2011.10.006     Document Type: Review

References (72)

1. R.K. Sunahara, and R. Taussig Isoforms of mammalian adenylyl cyclase: multiplicities of signalling Mol. Interv. 2 2002 168 184
2. R. Sadana, and C.W. Dessauer Physiological roles for G protein-regulated adenylyl cyclase isoforms: insights from knockout and overexpression studies Neurosignals 17 2009 5 22
3. S. Pierre Capturing adenylyl cyclases as potential drug targets Nat. Rev. Drug Discov. 8 2009 321 335
4. A. Laurenza Forskolin: a specific stimulator of adenylyl cyclase or a diterpene with multiple sites of action? Trends Pharmacol. Sci. 10 1989 442 447 (Pubitemid 19264294)
5. W. Putnam Identification of a forskolin-like molecule in human renal cysts J. Am. Soc. Nephrol. 18 2007 934 943 (Pubitemid 46434510)
6. D. Ho Modulation of β-adrenergic receptor signalling in heart failure and longevity targeting adenylyl cyclase type 5 Heart Fail. Rev. 15 2010 495 512
7. V.J. Watts Adenylyl cyclase isoforms as novel therapeutic targets: an exciting example of excitotoxicity neuroprotection Mol. Interv. 7 2007 70 73 (Pubitemid 46683176)
8. H. Wang Identification of an adenylyl cyclase inhibitor for treating neuropathic and inflammatory pain Sci. Transl. Med. 3 2011 65ra3
9. A. Gille, and R. Seifert 2′(3′)-O-(N-methylanthraniloyl)- substituted GTP analogs: a novel class of potent competitive adenylyl cyclase inhibitors J. Biol. Chem. 278 2003 12672 12679 (Pubitemid 36800027)
10. C.W. Dessauer The interactions of adenylate cyclases with P-site inhibitors Trends Pharmacol. Sci. 20 1999 205 210
11. M. Erdorf, and R. Seifert Impact of divalent cations on regulation of adenylyl cyclase isoforms by forskolin analogs Biochem. Pharmacol. 82 2011 1673 1681
12. A. Haunsø Small ligands modulating the activity of mammalian adenylyl cyclases: a novel mode of inhibition by calmidazolium Mol. Pharmacol. 63 2003 624 631 (Pubitemid 36297333)
13. R.J. Haslam Inhibition of adenylate cyclase by adenosine analogues in preparations of broken and intact platelets Biochem. J. 176 1978 83 95
14. T. Onda Type-specific regulation of adenylyl cyclase. Selective pharmacological stimulation and inhibition of adenylyl cyclase isoforms J. Biol. Chem. 276 2001 47785 47793
15. R.A. Johnson Isozyme-dependent sensitivity of adenylyl cyclase to P-site-mediated inhibition by adenine nucleosides and nucleoside 3′-polyphosphates J. Biol. Chem. 272 1997 8962 8966 (Pubitemid 27154894)
16. C. Lippe, and C. Ardizzone Actions of vasopressin and isoprenaline on the ionic transport across the isolated frog skin in the presence and the absence of adenylyl cyclase inhibitors MDL12330A and SQ22536 Comp. Biochem. Physiol. C 99 1991 209 211
17. R. Whitley Vidarabine: a preliminary review of its pharmacological properties and therapeutic use Drugs 20 1980 267 282 (Pubitemid 11191900)
18. K. Iwatsubo Direct inhibition of type 5 adenylyl cyclase prevents myocardial apoptosis without functional deterioration J. Biol. Chem. 279 2004 40938 40945 (Pubitemid 39287693)
19. M.C. Ortiz-Capisano Adenylyl cyclase isoform V mediates renin release from juxtaglomerular cells Hypertension 49 2007 618 624
20. F. Aldehni Stimulation of renin secretion by catecholamines is dependent on adenylyl cyclases 5 and 6 Hypertension 57 2011 460 468
21. C. Rangel-Barajas L-DOPA-induced dyskinesia in hemiparkinsonian rats is associated with up-regulation of adenylyl cyclase type V/VI and increased GABA release in the substantia nigra reticulata Neurobiol. Dis. 41 2011 51 61
22. A. Gille Differential inhibition of adenylyl cyclase isoforms and soluble guanylyl cyclase by purine and pyrimidine nucleotides J. Biol. Chem. 279 2004 19955 19969 (Pubitemid 38623438)
23. T.C. Mou Structural basis for the inhibition of mammalian membrane adenylyl cyclase by 2′ (3′)-O-(N-methylanthraniloyl)-guanosine 5′-triphosphate J. Biol. Chem. 280 2005 7253 7261
24. T.C. Mou Broad specificity of mammalian adenylyl cyclase for interaction with 2′,3′-substituted purine and pyrimidine nucleotide inhibitors Mol. Pharmacol. 70 2006 878 886
25. M. Hübner Structural basis for the high-affinity inhibition of mammalian membranous adenylyl cyclase by 2′,3′-O-(N- methylanthraniloyl)-inosine 5′-triphosphate Mol. Pharmacol. 80 2011 87 96
26. J. Geduhn Bis-halogen-anthraniloyl-substituted nucleoside 5′-triphosphates as potent and selective inhibitors of Bordetella pertussis adenylyl cyclase toxin J. Pharmacol. Exp. Ther. 336 2011 104 115
27. S. Suryanarayana Differential inhibition of various adenylyl cyclase isoforms and soluble guanylyl cyclase by 2′,3′-O-(2,4,6- trinitrophenyl)-substituted nucleoside 5′-triphosphates J. Pharmacol. Exp. Ther. 330 2009 687 695
28. C. Pinto Structure-activity relationships for the interactions of 2′- and 3′-(O)-(N-methyl)anthraniloyl-substituted purine and pyrimidine nucleotides with mammalian adenylyl cyclases Biochem. Pharmacol. 82 2011 358 370
29. M. Göttle Characterization of mouse heart adenylyl cyclase J. Pharmacol. Exp. Ther. 329 2009 1156 1165
30. M. Hübner Effect of MANT-nucleotides on L-type calcium currents in murine cardiomyocytes Naunyn-Schmiedeberg's Arch. Pharmacol. 383 2011 573 583
31. D.M. Jameson, and J.F. Watts Fluorescent nucleotide analogs: synthesis and applications Methods Enzymol. 278 1997 363 390 (Pubitemid 27229929)
32. K.B. Seamon Forskolin: unique diterpene activator of adenylate cyclase in membranes and in intact cells Proc. Natl. Acad. Sci. U.S.A. 78 1981 3363 3367 (Pubitemid 11059290)
33. sα Biochemistry 33 1994 12852 12859
34. C. Pinto Activation and inhibition of adenylyl cyclase isoforms by forskolin analogs J. Pharmacol. Exp. Ther. 325 2008 27 36 (Pubitemid 351439155)
35. 125I]-Labeled forskolin analogs which discriminate adenylyl cyclase and a glucose transporter: pharmacological characterization and localization of binding sites in rat brain by in vitro receptor autoradiography J. Pharmacol. Exp. Ther. 263 1992 1415 1423 (Pubitemid 23157225)
36. R.K. Sunahara Exchange of substrate and inhibitor specificities between adenylyl and guanylyl cyclases J. Biol. Chem. 273 1998 16332 16338 (Pubitemid 28311412)
37. D. Fabbro Protein kinases as targets for anticancer agents: from inhibitors to useful drugs Pharmacol. Ther. 93 2002 79 98 (Pubitemid 34615551)
38. J.J. Tesmer Molecular basis for P-site inhibition of adenylyl cyclase Biochemistry 39 2000 14464 14471
39. 3H]forskolin to rat brain membranes Proc. Natl. Acad. Sci. U.S.A. 81 1984 5081 5085 (Pubitemid 14008884)
40. C. Pinto Differential interactions of the catalytic subunits of adenylyl cyclase with forskolin analogs Biochem. Pharmacol. 78 2009 62 69
41. 2+ entry mediated via TRPC6 channels. J. Pharmacol. Exp. Ther. (in press)
42. K.S. Kim, and P.L. Han Mice lacking adenylyl cyclase-5 cope badly with repeated restraint stress J. Neurosci. Res. 87 2009 2983 2993
43. K.S. Kim Mice lacking adenylyl cyclase type 5 (AC5) show increased ethanol consumption and reduced ethanol sensitivity Psychopharmacology (Berl.) 215 2011 391 398
44. T. Iwamoto Motor dysfunction in type 5 adenylyl cyclase-null mice J. Biol. Chem. 278 2003 16936 16940 (Pubitemid 36799567)
45. T. Tang Adenylyl cyclase 6 deletion reduces left ventricular hypertrophy, dilation, dysfunction, and fibrosis in pressure-overloaded female mice J. Am. Coll. Cardiol. 55 2010 1476 1486
46. J.P. Pieroni Distinct characteristics of the basal activities of adenylyl cyclases 2 and 6 J. Biol. Chem. 270 1995 21368 21373
47. R. Seifert, and K. Wenzel-Seifert Constitutive activity of G-protein-coupled receptors: cause of disease and common property of wild-type receptors Naunyn-Scmiedeberg's Arch. Pharmacol. 366 2002 381 416 (Pubitemid 35251788)
48. E. Schneider, and R. Seifert Sf9 cells: a versatile model system to investigate the pharmacological properties of G protein-coupled receptors Pharmacol. Ther. 128 2010 387 418
49. Y. Shen Selective inhibition of anthrax edema factor by adefovir, a drug for chronic hepatitis B virus infection Proc. Natl. Acad. Sci. U.S.A. 101 2004 3242 3247 (Pubitemid 38327765)
50. C.W. Dessauer Adenylyl cyclase-A-kinase anchoring protein complexes: the next dimension of cAMP signalling Mol. Pharmacol. 76 2009 935 941
51. C.-L. Hu Adenylyl cyclase type 5 protein expression during cardiac development Am. J. Physiol. Heart Circ. Physiol. 297 2009 H1776 H1782
52. M.C. Michel How reliable are G-protein-coupled receptor antibodies? Naunyn-Schmiedeberg's Arch. Pharmacol. 379 2009 385 388
53. M. Erdorf, and R. Seifert Pharmacological characterization of adenylyl cyclase isoforms in rabbit kidney membranes Naunyn-Schmiedeberg's Arch. Pharmacol. 383 2011 357 372
54. T. Wang, and M.J. Brown Differential expression of adenylyl cyclase subtypes in human cardiovascular system Mol. Cell. Endocrinol. 223 2004 55 62 (Pubitemid 38992910)
55. 4 receptors in Sf9 insect cells Naunyn-Schmiedeberg's Arch. Pharmacol. 383 2011 457 470
56. B.M. Hacker Cloning, chromosomal mapping, and regulatory properties of the human type 9 adenylyl cyclase (ADCY9) Genomics 50 1998 97 104 (Pubitemid 28280885)
57. W.H. Laux Pro-nucleotide inhibitors of adenylyl cyclases in intact cells J. Biol. Chem. 279 2004 13317 13332 (Pubitemid 38468854)
58. B.K. Kobilka Structural insights into adrenergic receptor function and pharmacology Trends Pharmacol. Sci. 32 2011 213 218
59. M. Jaleel Tyrphostins are inhibitors of guanylyl and adenylyl cyclases Biochemistry 43 2004 8247 8255 (Pubitemid 38808280)
60. D. Rottländer Functional adenylyl cyclase inhibition in murine cardiomyocytes by 2′(3′)-O-(N-methylanthraniloyl)-guanosine 5′-[γ-thio]triphosphate J. Pharmacol. Exp. Ther. 321 2007 608 615 (Pubitemid 46624491)
61. C.L. Tucker Two amino acid substitutions convert a guanylyl cyclase, RetGC-1, into an adenylyl cyclase Proc. Natl. Acad. Sci. U.S.A. 95 1998 5993 5997 (Pubitemid 28248952)
62. R. Seifert, and G. Schultz Involvement of pyrimidinoceptors in the regulation of cell functions by uridine and uracil nucleotides Trends Pharmacol. Sci. 10 1989 365 369 (Pubitemid 19222518)
63. Taha, H. et al. (2011) Inhibition of the adenylyl cyclase toxin, edema factor, from Bacillus anthracis by a series of 18 mono- and bis-(M)ANT- substituted nucleoside 5′-triphosphates. Naunyn-Schmiedeberg's Arch. Pharmacol. (in press)
64. A. Gille Differential interactions of G-proteins and adenylyl cyclase with nucleoside 5′-triphosphates, nucleoside 5′-[γ-thio] triphosphates and nucleoside 5′-[β,γ-imido]triphosphates Biochem. Pharmacol. 71 2005 89 97 (Pubitemid 41713530)
65. 3-adrenoceptor-mediated relaxation of internal anal sphincter smooth muscle J. Pharmacol. Exp. Ther. 308 2004 1111 1120 (Pubitemid 38263988)
66. S. Copsel Mutidrug resistance protein 4 (MRP4/ABCC4) regulates cAMP cellular levels and controls human leukemia cell proliferation and differentiation J. Biol. Chem. 286 2011 6979 6988
67. G. Grupp Effects of RMI 12330A, a new inhibitor of adenylate cyclase on mycocardial function and subcellular activity Br. J. Pharmacol. 70 1980 429 442 (Pubitemid 11241414)
68. A. Gadea The adenylate cyclase inhibitor MDL-12330A has a non-specific effect on glycine transport in Müller cells from the retina Brain Res. 838 1999 200 204 (Pubitemid 29389835)
69. M. Spehr Particulate adenylate cyclase plays a key role in human sperm olfactory receptor-mediated chemotaxis J. Biol. Chem. 279 2004 40194 40203 (Pubitemid 39258295)
70. M.E. Ferretti MDL 12330 inhibits the non-neuronal adenylyl cyclase from the freshwater snail Planorbarius corneus, but the neuronal enzyme is activated by this compound Neurosci. Lett. 207 1996 191 194 (Pubitemid 26117607)
71. J.D. Johnson, and L.A. Wittenauer A fluorescent calmodulin that reports the binding of hydrophobic inhibitory ligands Biochem. J. 211 1983 473 479 (Pubitemid 13092537)
72. M. Zimmer, and F. Hofmann Calmodulin antagonists inhibit activity of myosin light-chain kinase independent of calmodulin Eur. J. Biochem. 142 1984 393 397 (Pubitemid 14093624)