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Volumn 52, Issue 21, 2009, Pages 6588-6598

Isosorbide-based aspirin prodrugs: Integration of nitric oxide releasing groups

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLSALICYLIC ACID; CYCLOOXYGENASE 1; ESTER DERIVATIVE; ISOSORBIDE; ISOSORBIDE 2 ASPIRINATE 5 (2 METHYLBENZOATE); ISOSORBIDE 2 ASPIRINATE 5 (2 NITROXYMETHYL)BENZOATE; ISOSORBIDE 2 ASPIRINATE 5 (3 HYDROXYBENZOATE); ISOSORBIDE 2 ASPIRINATE 5 (3 METHYLBENZOATE); ISOSORBIDE 2 ASPIRINATE 5 (3 NITROOXYMETHYL)BENZOATE; ISOSORBIDE 2 ASPIRINATE 5 (4 HYDROXYBENZOATE); ISOSORBIDE 2 ASPIRINATE 5 (4 METHYL 1,2,3 THIADIAZOLE 5 OATE); ISOSORBIDE 2 ASPIRINATE 5 (4 NITROOXYMETHYL)BENZOATE; ISOSORBIDE 2 ASPIRINATE 5 [1 METHYL (1H) PYRAZOLE 5 CARBOXYLATE]; ISOSORBIDE 2 ASPIRINATE 5 ACETATE; ISOSORBIDE 2 ASPIRINATE 5 BENZOATE; ISOSORBIDE 2 ASPIRINATE 5 CYCLOPROPANOATE; ISOSORBIDE 2 ASPIRINATE 5 ESTER; ISOSORBIDE 2 ASPIRINATE 5 ISO NICOTINATE; ISOSORBIDE 2 ASPIRINATE 5 NICOTINATE; ISOSORBIDE 2 ASPIRINATE 5 PENTANOATE; ISOSORBIDE 2 ASPIRINATE 5 PROPIONATE; ISOSORBIDE 2ASPIRNATE 5 (4 PHENYLBENZOATE); ISOSORBIDE 5 MONONITRATE 2 ASPIRINATE; ISOSORBIDE 5 NITRATE; NITRATE; NITRIC OXIDE; PROSTAGLANDIN SYNTHASE; UNCLASSIFIED DRUG;

EID: 71049183971     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900561s     Document Type: Article
Times cited : (26)

References (41)
  • 2
    • 0028354308 scopus 로고
    • Aspirin as an antiplatelet drug
    • (b) Patrono, C. Aspirin as an antiplatelet drug. N. Engl. J. Med. 1994, 330, 1287-1294.
    • (1994) N. Engl. J. Med. , vol.330 , pp. 1287-1294
    • Patrono, C.1
  • 3
    • 33744469580 scopus 로고    scopus 로고
    • Lipid mediators: Lipoxin and aspirin-triggered 15-epi-lipoxins
    • Romano, M. Lipid mediators: lipoxin and aspirin-triggered 15-epilipoxins. Inflamm. Allergy Drug Targets 2006, 5, 81-90. (Pubitemid 43796670)
    • (2006) Inflammation and Allergy - Drug Targets , vol.5 , Issue.2 , pp. 81-90
    • Romano, M.1
  • 4
    • 34248157118 scopus 로고    scopus 로고
    • Effect of aspirin on long-term risk of colorectal cancer: Consistent evidence from randomised and observational studies
    • British Doctors Aspirin Trial and the UKTIA Aspirin Trial
    • Flossmann, E.; Rothwell, P. M. Effect of aspirin on long-term risk of colorectal cancer: consistent evidence from randomised and observational studies. British Doctors Aspirin Trial and the UKTIA Aspirin Trial. Lancet 2007, 369, 1603-1613.
    • (2007) Lancet , vol.369 , pp. 1603-1613
    • Flossmann, E.1    Rothwell, P.M.2
  • 6
    • 0030000385 scopus 로고    scopus 로고
    • The role of anti-inflammatory drugs in the prevention and treatment of Alzheimer's disease
    • Breitner, J. C. S. The role of anti-inflammatory drugs in the prevention and treatment of Alzheimer's disease. Annu. Rev. Med. 1996, 47, 401-411.
    • (1996) Annu. Rev. Med. , vol.47 , pp. 401-411
    • Breitner, J.C.S.1
  • 7
    • 0036828646 scopus 로고    scopus 로고
    • Risk of upper gastrointestinal bleeding in patients taking low-dose aspirin for the prevention of cardiovascular diseases
    • (a) Serrano, P.; Lanas, A.; Arroyo, M. T.; Ferreira, I. J. Risk of upper gastrointestinal bleeding in patients taking low-dose aspirin for the prevention of cardiovascular diseases. Aliment. Pharmacol. Ther. 2002, 16, 1945-1953.
    • (2002) Aliment. Pharmacol. Ther. , vol.16 , pp. 1945-1953
    • Serrano, P.1    Lanas, A.2    Arroyo, M.T.3    Ferreira, I.J.4
  • 8
    • 0025374873 scopus 로고
    • The effect of chronic aspirin use on duodenal and gastric ulcer hospitalisation
    • (b) Kurata, J. H.; Abbey, D. E. The effect of chronic aspirin use on duodenal and gastric ulcer hospitalisation. J. Clin. Gastroenterol. 1990, 12, 260-266.
    • (1990) J. Clin. Gastroenterol. , vol.12 , pp. 260-266
    • Kurata, J.H.1    Abbey, D.E.2
  • 9
    • 0002907014 scopus 로고
    • Effects of very low doses of aspirin (ASA) on gastric, duodenal and rectal prostaglandins (PGs) & mucosal injury
    • (c) Cryer, B.; Luk, G.; Feldman, M. Effects of very low doses of aspirin (ASA) on gastric, duodenal and rectal prostaglandins (PGs) & mucosal injury. Gastroenterology 1995, 108, A77.
    • (1995) Gastroenterology , vol.108
    • Cryer, B.1    Luk, G.2    Feldman, M.3
  • 10
    • 0037349262 scopus 로고    scopus 로고
    • Aspirin for the prevention of cardiovascular disease: Calculating benefit and harm in the individual patient
    • Loke, Y. K.; Bell, A.; Derry, S. Aspirin for the prevention of cardiovascular disease: calculating benefit and harm in the individual patient. Br. J. Clin. Pharmacol. 2003, 55, 282-287.
    • (2003) Br. J. Clin. Pharmacol. , vol.55 , pp. 282-287
    • Loke, Y.K.1    Bell, A.2    Derry, S.3
  • 11
    • 0030599533 scopus 로고    scopus 로고
    • Risk of aspirin-associated major upper-gastrointestinal bleeding with enteric-coated or buffered product
    • DOI 10.1016/S0140-6736(96)01254-8
    • Kelly, J. P.; Kaufman, D. W.; Jurgelon, J. M.; Sheehan, J.; Koff, R. S.; Shapiro, S. Risk of aspirin-associated major upper-gastrointestinal bleeding with enteric-coated or buffered product. Lancet 1996, 348, 1413-1416. (Pubitemid 26395236)
    • (1996) Lancet , vol.348 , Issue.9039 , pp. 1413-1416
    • Kelly, J.P.1    Kaufman, D.W.2    Jurgelon, J.M.3    Sheehan, J.4    Koff, R.S.5    Shapiro, S.6
  • 13
    • 0020660552 scopus 로고
    • Aspirin can inhibit gastric mucosal cyclo-oxygenase without causing lesions in the rat
    • Ligumsky, M.; Golanska, E. M.; Hansen, D. G.; Kauffman, G. L. Aspirin can inhibit gastric mucosal cyclo-oxygenase without causing lesions in the rat. Gastroenterology 1983, 84, 756-761.
    • (1983) Gastroenterology , vol.84 , pp. 756-761
    • Ligumsky, M.1    Golanska, E.M.2    Hansen, D.G.3    Kauffman, G.L.4
  • 14
    • 0014669007 scopus 로고
    • Failure of intravenous aspirin to increase gastrointestinal blood loss
    • Cooke, A. R.; Goulston, K. Failure of intravenous aspirin to increase gastrointestinal blood loss. Br. Med. J. 1969, 4, 330-332.
    • (1969) Br. Med. J. , vol.4 , pp. 330-332
    • Cooke, A.R.1    Goulston, K.2
  • 16
    • 0032802682 scopus 로고    scopus 로고
    • NO-aspirins: A class of new anti-inflammatory and antithrombotic agents
    • (a) Del Soldato, P.; Sorrentino, R.; Pinto, A. NO-aspirins: a class of new anti-inflammatory and antithrombotic agents. Trends Pharmacol. Sci. 1999, 20, 319-323.
    • (1999) Trends Pharmacol. Sci. , vol.20 , pp. 319-323
    • Del Soldato, P.1    Sorrentino, R.2    Pinto, A.3
  • 17
    • 33845715319 scopus 로고    scopus 로고
    • Pharmacologic profile and therapeutic potential of NCX 4016, a nitric oxide-releasing aspirin, for cardiovascular disorders
    • (b) Gresele, P.; Momi, S. Pharmacologic profile and therapeutic potential of NCX 4016, a nitric oxide-releasing aspirin, for cardiovascular disorders. Cardiovasc. Drug Rev. 2006, 24 (2), 148-168
    • (2006) Cardiovasc. Drug Rev. , vol.24 , Issue.2 , pp. 148-168
    • Gresele, P.1    Momi, S.2
  • 18
    • 0032457409 scopus 로고    scopus 로고
    • Nitric oxide: A regulator of mucosal defense and injury
    • DOI 10.1007/s005350050178
    • Elliott, S. N.; Wallace, J. L. Nitric oxide: a regulator of mucosal defense and injury. J. Gastroenterol. 1998, 33, 792-803. (Pubitemid 29271539)
    • (1998) Journal of Gastroenterology , vol.33 , Issue.6 , pp. 792-803
    • Elliott, S.N.1    Wallace, J.L.2
  • 19
    • 0031874813 scopus 로고    scopus 로고
    • NO-aspirins: Anti-thrombotic activity of derivatives of acetyl-salicylic acid releasing nitric oxide
    • Minuz, P.; Lechi, C.; Zuliani, V.; Gaino, S.; Tommasoli, R.; Lechi, A. NO-aspirins: anti-thrombotic activity of derivatives of acetyl-salicylic acid releasing nitric oxide. Cardiovasc. Drug Rev. 1998, 16, 31-47.
    • (1998) Cardiovasc. Drug Rev. , vol.16 , pp. 31-47
    • Minuz, P.1    Lechi, C.2    Zuliani, V.3    Gaino, S.4    Tommasoli, R.5    Lechi, A.6
  • 21
    • 41149109145 scopus 로고    scopus 로고
    • Second-generation aspirin and indomethacin prodrugs possessing an O(2)-(acetoxymethyl)-1-(2-carboxypyrrolidin-1-yl)-diazenium-1,2-diolate nitric oxide donor moiety: Design, synthesis, biological evaluation, and nitric oxide release studies
    • Velázquez, C. A.; Chen, Q. H.; Citro, M. L.; Keefer, L. K.; Knaus, E. E. Second-generation aspirin and indomethacin prodrugs possessing an O(2)-(acetoxymethyl)-1-(2-carboxypyrrolidin-1-yl)-diazenium-1,2-diolate nitric oxide donor moiety: design, synthesis, biological evaluation, and nitric oxide release studies. J. Med. Chem. 2008, 51, 1954-1961.
    • (2008) J. Med. Chem. , vol.51 , pp. 1954-1961
    • Velázquez, C.A.1    Chen, Q.H.2    Citro, M.L.3    Keefer, L.K.4    Knaus, E.E.5
  • 23
    • 0024555828 scopus 로고
    • Evaluation of glycolamide esters and various other esters of aspirin as true aspirin prodrugs
    • Nielsen, N. M.; Bungaard, H. Evaluation of glycolamide esters and various other esters of aspirin as true aspirin prodrugs. J. Med. Chem. 1989, 32, 727-734.
    • (1989) J. Med. Chem. , vol.32 , pp. 727-734
    • Nielsen, N.M.1    Bungaard, H.2
  • 24
    • 34247847900 scopus 로고    scopus 로고
    • Evaluation of nitrate-substituted pseudocholine esters of aspirin as potential nitroaspirins
    • Gilmer, J. F.; Moriarty, L. M.; Clancy, J. M. Evaluation of nitrate-substituted pseudocholine esters of aspirin as potential nitroaspirins. Bioorg. Med. Chem. Lett. 2007, 17, 3217-3220
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 3217-3220
    • Gilmer, J.F.1    Moriarty, L.M.2    Clancy, J.M.3
  • 26
    • 0034822731 scopus 로고    scopus 로고
    • Synthesis, hydrolysis kinetics and anti-platelet effects of isosorbide mononitrate derivatives of aspirin
    • (a) Gilmer, J. F.; Moriarty, L. M.; McCafferty, D. F.; Clancy, J. M. Synthesis, hydrolysis kinetics and anti-platelet effects of isosorbide mononitrate derivatives of aspirin. Eur J. Pharm. Sci. 2001, 14, 221-227.
    • (2001) Eur J. Pharm. Sci. , vol.14 , pp. 221-227
    • Gilmer, J.F.1    Moriarty, L.M.2    McCafferty, D.F.3    Clancy, J.M.4
  • 28
    • 0023910667 scopus 로고
    • Glycolamide esters as a novel biolabile prodrug type for nonsteroidal anti-inflammatory carboxylic acid drugs
    • Bundgaard, H.; Nielsen, N. M. Glycolamide esters as a novel biolabile prodrug type for nonsteroidal anti-inflammatory carboxylic acid drugs. Int. J. Pharm. 1988, 43, 101-110.
    • (1988) Int. J. Pharm. , vol.43 , pp. 101-110
    • Bundgaard, H.1    Nielsen, N.M.2
  • 30
    • 0015310639 scopus 로고
    • Systemic and coronary vascular effects of the 2- And 5-mononitrate esters of isosorbide dinitrate
    • (b)Wendt, R. L. Systemic and coronary vascular effects of the 2- and 5-mononitrate esters of isosorbide dinitrate. J. Pharmacol. Exp. Ther. 1972, 180, 732-742.
    • (1972) J. Pharmacol. Exp. Ther. , vol.180 , pp. 732-742
    • Wendt, R.L.1
  • 32
    • 0001469485 scopus 로고
    • Cleavage of carboxylic acid esters to acid chlorides with dichlorotriphenylphosphorane
    • Burton, D. J.; Koppes, W. M. Cleavage of carboxylic acid esters to acid chlorides with dichlorotriphenylphosphorane. J. Org. Chem. 1975, 40, 3026-3032.
    • (1975) J. Org. Chem. , vol.40 , pp. 3026-3032
    • Burton, D.J.1    Koppes, W.M.2
  • 34
    • 2642683292 scopus 로고
    • Notes; An Attempted Synthesis of Phenyl Nitrate
    • Chaney, A.; Wolfrom, M. Notes; An Attempted Synthesis of Phenyl Nitrate. J. Org. Chem. 1961, 26, 2998.
    • (1961) J. Org. Chem. , vol.26 , pp. 2998
    • Chaney, A.1    Wolfrom, M.2
  • 35
    • 0027184248 scopus 로고
    • Direct inhibition of platelet function by organic nitrates via nitric oxide formation
    • Weber, A. A.; Strobach, H; Schror, K. Direct inhibition of platelet function by organic nitrates via nitric oxide formation. Eur. J. Pharmacol. 1993, 247, 29-37.
    • (1993) Eur. J. Pharmacol. , vol.247 , pp. 29-37
    • Weber, A.A.1    Strobach, H.2    Schror, K.3
  • 38
    • 0142039868 scopus 로고    scopus 로고
    • Crystal structure of human butyrylcholinesterase and of its complexes with substrate and products
    • Nicolet, Y.; Lockridge, O.; Masson, P.; Fontecilla-Camps, J. C.; Nachon, F. Crystal structure of human butyrylcholinesterase and of its complexes with substrate and products. J. Biol. Chem. 2003, 278, 41141-41147.
    • (2003) J. Biol. Chem. , vol.278 , pp. 41141-41147
    • Nicolet, Y.1    Lockridge, O.2    Masson, P.3    Fontecilla-Camps, J.C.4    Nachon, F.5
  • 39
    • 33645687131 scopus 로고    scopus 로고
    • Inhibition of human acetyl- And butyrylcholinesterase by novel carbamates of (-)- and (+)-tetrahydrofurobenzofuran and methanobenzodioxepine
    • Luo, W.; Yu, Q. S.; Kulkarni, S. S.; Parrish, D. A.; Holloway, H. W.; Tweedie, D.; Shafferman, A.; Lahiri, D. K.; Brossi, A.; Greig, N. H. Inhibition of human acetyl- and butyrylcholinesterase by novel carbamates of (-)- and (+)-tetrahydrofurobenzofuran and methanobenzodioxepine. J. Med. Chem. 2006, 49, 2174-2185.
    • (2006) J. Med. Chem. , vol.49 , pp. 2174-2185
    • Luo, W.1    Yu, Q.S.2    Kulkarni, S.S.3    Parrish, D.A.4    Holloway, H.W.5    Tweedie, D.6    Shafferman, A.7    Lahiri, D.K.8    Brossi, A.9    Greig, N.H.10
  • 40
    • 11644261806 scopus 로고    scopus 로고
    • Automated docking using a Lamarckian genetic algorithmand an empirical binding free energy function
    • Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using a Lamarckian genetic algorithmand an empirical binding free energy function. J. Comput. Chem. 1998, 19, 1639-1662.
    • (1998) J. Comput. Chem. , vol.19 , pp. 1639-1662
    • Morris, G.M.1    Goodsell, D.S.2    Halliday, R.S.3    Huey, R.4    Hart, W.E.5    Belew, R.K.6    Olson, A.J.7
  • 41
    • 33644811612 scopus 로고
    • A New and Rapid Colorimetric Determination of Acetylcholinesterase Activity
    • Ellman, G. L.; Courtney, K. D.; Andres, V.; Featherstone, R. M. A New and Rapid Colorimetric Determination of Acetylcholinesterase Activity. Biochem. Pharmacol. 1961, 7, 88-95.
    • (1961) Biochem. Pharmacol. , vol.7 , pp. 88-95
    • Ellman, G.L.1    Courtney, K.D.2    Andres, V.3    Featherstone, R.M.4


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