Carbaboranes as pharmacophores: Similarities and differences between aspirin and asborin

European Journal of Medicinal Chemistry

Volumn 46, Issue 4, 2011, Pages 1131-1139

  Scholz, Matthias ^a   Kaluerović, Goran N ^b   Kommera, Harish ^b   Paschke, Reinhard ^b   Will, Joanna ^c   Sheldrick, William S ^c   Hey Hawkins, Evamarie ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^c RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

Asborin; Aspirin; Carbaborane; Carborane; Cytotoxicity; Pharmacophore

Indexed keywords

3 CARBABORANE; 4 CARBABORANE; ACETYLSALICYLIC ACID; ANTINEOPLASTIC AGENT; ASBORIN; BORIC ACID; CARBABORANE DERIVATIVE; CISPLATIN; CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; PROSTAGLANDIN SYNTHASE; SALBORIN; SALICYLIC ACID; SODIUM 7 ACETOXY 7,8 DICARBANIDOUNDECABORATE 8 CARBOXYLIC ACID; TETRAETHYLAMMONIUM 7 HYDROXY 7,8 DICARBANIDOUNDECABORATE 8 CARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG SAFETY; DRUG SCREENING; DRUG STABILITY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; HYDROPHOBICITY; IC 50; PHARMACOPHORE;

ACETATES; APOPTOSIS; ASPIRIN; BORON COMPOUNDS; CASPASES; CATALYTIC DOMAIN; CELL LINE, TUMOR; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; DRUG DISCOVERY; HUMANS; HYDROLYSIS; ISOMERISM; MODELS, MOLECULAR; RHODAMINES;

EID: 79952283306     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.01.030     Document Type: Article

References (53)

1. T.L. Heying, J.W. Ager, S.L. Clark, D.J. Mangold, H.L. Goldstein, M. Hillman, R.J. Polak, and J.W. Szymanski A new series of organoboranes. I. Carboranes from the reaction of decaborane with acetylenic compounds Inorg. Chem. 2 1963 1089 1092
2. M.M. Fein, J. Bobinski, N. Mayes, N. Schwartz, and M.S. Cohen Carboranes. I. The preparation and chemistry of 1-isopropenylcarborane and its derivatives (a new family of stable clovoboranes) Inorg. Chem. 2 1963 1111 1115
3. 12 and their derivatives Chem. Rev. 92 1992 209 223
4. R. Hoffmann Brücken zwischen Anorganischer und Organischer Chemie (Nobel-Vortrag) Angew. Chem. 94 1982 725 739
5. D. Grafstein, and J. Dvorak Neocarboranes, a new family of stable organoboranes isomeric with the carboranes Inorg. Chem. 2 1963 1128 1133
6. n Inorg. Chem. 37 1998 3454 3470 (Pubitemid 128485860)
7. K. Hermansson, M. Wjcik, and S. Sjberg o-, m-, and p-carboranes and their anions: ab initio calculations of structures, electron affinities, and acidities Inorg. Chem. 38 1999 6039 6048
8. A.F. Armstrong, and J.F. Valliant The bioinorganic and medicinal chemistry of carboranes: from new drug discovery to molecular imaging and therapy Dalton Trans. 2007 4240 4251 (Pubitemid 47485645)
9. M.F. Hawthorne, D.C. Young, P.M. Garrett, D.A. Owen, S.G. Schwerin, F.N. Tebbe, and P.A. Wegner Preparation and characterization of the (3)-1,2- and (3)-1,7-dicarbadodecahydroundecaborate(-1) ions J. Am. Chem. Soc. 90 1968 862 868
10. C.L. Powell, M. Schulze, S.J. Black, A.S. Thompson, and M.D. Threadgill Closo - > nido cage degradation of 1-(substituted-phenyl)-1,2- dicarbadodecaborane(12)s in wet DMSO under neutral conditions Tetrahedron Lett. 48 2007 1251 1254 (Pubitemid 46097026)
11. J. Yoo, J.W. Hwang, and Y. Do Facile and mild deboronation of o-carboranes using cesium fluoride Inorg. Chem. 40 2001 568 570 (Pubitemid 33064954)
12. 12 Dalton Trans. 2002 2132 2141 (Pubitemid 35188404)
13. Y. Endo, T. Sawabe, and Y. Taoda Electronic effects of icosahedral carboranes. Retentive solvolysis of (1,2-dicarba-closo-dodecaboran-1-yl)benzyl p-toluenesulfonates J. Am. Chem. Soc. 122 2000 180 181 (Pubitemid 30054109)
14. M.F. Hawthorne, D.C. Young, and P.A. Wegner Carbametallic boron hydride derivatives. I. Apparent analogs of ferrocene and ferricinium ion J. Am. Chem. Soc. 87 1965 1818 1819
15. S. Bauer, S. Tschirschwitz, P. Lönnecke, R. Frank, B. Kirchener, M.L. Clarke, and E. Hey-Hawkins Enantiomerically pure bis(phosphanyl) carbaborane(12) compounds Eur. J. Inorg. Chem. 2009 2009 2776 2788
16. T.M. Keller Oxidative protection of carbon fibers with poly(carborane-siloxane-acetylene) Carbon 40 2002 225 229 (Pubitemid 34100059)
17. J.F. Valliant, K.J. Guenther, A.S. King, P. Morel, P. Schaffer, O.O. Sogbein, and K.A. Stephenson The medicinal chemistry of carboranes Coord. Chem. Rev. 232 2002 173 230
18. G.W. Kabalka, and M.L. Yao The synthesis and use of boronated amino acids for boron neutron capture therapy Anticancer Agents Med. Chem. 6 2006 111 125 (Pubitemid 43796647)
19. M.F. Hawthorne, and A. Maderna Applications of radiolabeled boron clusters to the diagnosis and treatment of cancer Chem. Rev. 99 1999 3421 3434 (Pubitemid 129589124)
20. Y. Endo, T. Yoshimi, and Y. Yamakoshi New estrogenic antagonists bearing dicarba-closo-dodecaborane as a hydrophobic pharmacophore Chem. Pharm. Bull. 48 2000 312 314 (Pubitemid 30136967)
21. J.F. Valliant, P. Schaffer, K.A. Stephenson, and J.F. Britten Synthesis of boroxifen, a nido-carborane analogue of tamoxifen J. Org. Chem. 67 2002 383 387 (Pubitemid 34101239)
22. R.C. Reynolds, S.R. Campbell, R.G. Fairchild, R.L. Kisliuk, P.L. Micca, S.F. Queener, J.M. Riordan, W.D. Sedwick, W.R. Waud, A.K. Leung, R.W. Dixon, W.J. Suling, and D.W. Borhani Novel boron-containing, nonclassical antifolates: synthesis and preliminary biological and structural evaluation J. Med. Chem. 50 2007 3283 3289 (Pubitemid 47065977)
23. R.L. Julius, O.K. Farha, J. Chiang, L.J. Perry, and M.F. Hawthorne Synthesis and evaluation of transthyretin amyloidosis inhibitors containing carborane pharmacophores Proc. Natl. Acad. Sci. U.S.A. 104 2007 4808 4813 (Pubitemid 47186132)
24. M. Scholz, K. Bensdorf, R. Gust, and E. Hey-Hawkins Asborin: the carbaborane analogue of aspirin ChemMedChem 4 2009 746 748
25. C.S. Williams, M. Mann, and R.N. DuBois The role of cyclooxygenases in inflammation, cancer, and development Oncogene 18 1999 7908 7916 (Pubitemid 30066236)
26. B. Hinz, and K. Brune Cyclooxygenase-2 - 10 years later J. Pharmacol. Exp. Ther. 300 2002 367 375 (Pubitemid 34106225)
27. J.R. Vane, R.J. Flower, and R.M. Botting History of aspirin and its mechanism of action Stroke 21 1990 IV12 23
28. G.P. Hochgesang, S.W. Rowlinson, and L.J. Marnett Tyrosine-385 is critical for acetylation of cyclooxygenase-2 by aspirin J. Am. Chem. Soc. 122 2000 6514 6515 (Pubitemid 30481762)
29. M. Lecomte, O. Laneuville, C. Ji, D.L. DeWitt, and W.L. Smith Acetylation of human prostaglandin endoperoxide synthase-2 (cyclooxygenase-2) by aspirin J. Biol. Chem. 269 1994 13207 13215 (Pubitemid 24206086)
30. D.A. Wolters, M.P. Washburn, and J.R. Yates 3rd An automated multidimensional protein identification technology for shotgun proteomics Anal. Chem. 73 2001 5683 5690 (Pubitemid 33126725)
31. B.S. Selinsky, K. Gupta, C.T. Sharkey, and P.J. Loll Structural analysis of NSAID binding by prostaglandin H2 synthase: time-dependent and time-independent inhibitors elicit identical enzyme conformations Biochemistry 40 2001 5172 5180 (Pubitemid 32373999)
32. A.S. Kalgutkar, B.C. Crews, S.W. Rowlinson, C. Garner, K. Seibert, and L.J. Marnett Aspirin-like molecules that covalently inactivate cyclooxygenase-2 Science 280 1998 1268 1270 (Pubitemid 28269622)
33. I. Ott, B. Kircher, C.P. Bagowski, D.H. Vlecken, E.B. Ott, J. Will, K. Bensdorf, W.S. Sheldrick, and R. Gust Modulation of the biological properties of aspirin by formation of a bioorganometallic derivative Angew. Chem. Int. Ed. Engl. 48 2009 1160 1163
34. C. Davison Salicylate metabolism in man Ann. N. Y. Acad. Sci. 179 1971 249 268
35. J. Paterson, G. Baxter, J. Lawrence, and G. Duthie Is there a role for dietary salicylates in health? Proc. Nutr. Soc. 65 2006 93 96 (Pubitemid 43259988)
36. Y. Taoda, T. Sawabe, Y. Endo, K. Yamaguchi, S. Fujii, and H. Kagechika Identification of an intermediate in the deboronation of ortho-carborane: an adduct of ortho-carborane with two nucleophiles on one boron atom Chem. Commun. 2008 2049 2051 (Pubitemid 351944410)
37. 11B NMR study of the tautomeric transformations of the 7,8-dicarba- nido-undecaborane(11) adducts with pyridine derivatives J. Struct. Chem. 40 1999 402 405
38. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney, and M.R. Boyd New colorimetric cytotoxicity assay for anticancer-drug screening J. Natl. Cancer Inst. 82 1990 1107 1112 (Pubitemid 20213250)
39. S. Elmore Apoptosis: a review of programmed cell death Toxicol. Pathol. 35 2007 495 516 (Pubitemid 46911891)
40. T. Ogawa, K. Ohta, T. Iijima, T. Suzuki, S. Ohta, and Y. Endo Synthesis and biological evaluation of p-carborane bisphenols and their derivatives: structure-activity relationship for estrogenic activity Bioorg. Med. Chem. 17 2009 1109 1117
41. T. Ogawa, K. Ohta, T. Yoshimi, H. Yamazaki, T. Suzuki, S. Ohta, and Y. Endo m-Carborane bisphenol structure as a pharmacophore for selective estrogen receptor modulators Bioorg. Med. Chem. Lett. 16 2006 3943 3946 (Pubitemid 43903227)
42. C.G. Wermuth, C.R. Ganellin, P. Lindberg, and L.A. Mitscher Glossary of terms used in medicinal chemistry (IUPAC Recommendations 1998) Pure Appl. Chem. 70 1998 1129 1143
43. M. Scholz, M. Steinhagen, J.T. Heiker, A.G. Beck-Sickinger, and E. Hey-Hawkins Asborin inhibits aldo/keto reductase 1A1 ChemMedChem. 6 2011 89 93
44. I.S. Park, J.R. Jo, H. Hong, K.Y. Nam, J.B. Kim, S.H. Hwang, M.S. Choi, N.H. Ryu, H.J. Jang, S.H. Lee, C.S. Kim, T.G. Kwon, G.Y. Park, J.W. Park, and B.C. Jang Aspirin induces apoptosis in YD-8 human oral squamous carcinoma cells through activation of caspases, down-regulation of Mcl-1, and inactivation of ERK-1/2 and AKT Toxicol. in Vitro 24 2010 713 720
45. N.R. Jana NSAIDs and apoptosis Cell. Mol. Life Sci. 65 2008 1295 1301
46. N. Ghosh, R. Chaki, V. Mandal, and S.C. Mandal COX-2 as a target for cancer chemotherapy Pharmacol. Rep. 62 2010 233 244
47. I.A. Voutsadakis, A. Patrikidou, K. Tsapakidis, A. Karagiannaki, E. Hatzidaki, N.E. Stathakis, and C.N. Papandreou Additive inhibition of colorectal cancer cell lines by aspirin and bortezomib Int. J. Colorectal Dis. 25 2010 795 804
48. K.H. Yan, C.J. Yao, H.Y. Chang, G.M. Lai, A.L. Cheng, and S.E. Chuang The synergistic anticancer effect of troglitazone combined with aspirin causes cell cycle arrest and apoptosis in human lung cancer cells Mol. Carcinog. 49 2010 235 246
49. D.L. Tab, J.K. Eng, and J.R. Yates Proteome Research: Mass Spectrometry 2001 Springer Verlag Heidelberg
50. SCALE3 ABSPACK: Empirical Absorption Correction, CrysAlis - Software Package 2006 Oxford Diffraction Ltd
51. A. Altomare, G. Cascarano, C. Giacovazzo, and A. Guagliardi Completion and refinement of crystal structures with SIR92 J. Appl. Crystallogr. 26 1993 343 350 (Pubitemid 23679266)
52. G.M. Sheldrick SHELXL-97, Program for the Refinement of Crystal Structures 1997 University of Göttingen Göttingen (Germany)
53. A. Dietrich, T. Mueller, R. Paschke, B. Kalinowski, T. Behlendorf, F. Reipsch, A. Fruehauf, H.J. Schmoll, C. Kloft, and W. Voigt 2-(4-(Tetrahydro-2H- pyran-2-yloxy)-undecyl)-propane-1,3-diamminedichloroplatinum(II): a novel platinum compound that overcomes cisplatin resistance and induces apoptosis by mechanisms different from that of cisplatin J. Med. Chem. 51 2008 5413 5422