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Volumn 39, Issue 17, 1996, Pages 3256-3262

Synthesis and in vitro and in vivo characteristics of an iodinated analogue of the β-adrenoceptor antagonist carazolol

Author keywords

[No Author keywords available]

Indexed keywords

3 ISOPROPYLAMINO 1 (7 METHYL 4 INDANYLOXY) 2 BUTANOL; 4 (3 TERT BUTYLAMINO 2 HYDROXYPROPOXY) 2 BENZIMIDAZOLONE; ATENOLOL; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; CARAZOLOL; CARAZOLOL DERIVATIVE; CYANOIODOPINDOLOL; IODINE 123; PROPRANOLOL; RADIOLIGAND; UNCLASSIFIED DRUG;

EID: 10144254436     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960122v     Document Type: Article
Times cited : (34)

References (28)
  • 1
    • 0027049068 scopus 로고
    • Importance of beta 2-adrenergic receptors in heart failure
    • Brodde, O. E.; Daul, A.; Michel, M. C.; Zerkowski, H. R. Importance of beta 2-adrenergic receptors in heart failure. Z. Kardiol. 1992, 81 (Suppl. 4), 71-78.
    • (1992) Z. Kardiol. , vol.81 , Issue.4 SUPPL. , pp. 71-78
    • Brodde, O.E.1    Daul, A.2    Michel, M.C.3    Zerkowski, H.R.4
  • 2
    • 0024337846 scopus 로고
    • Myocardial beta-adrenoceptor changes in heart failure: Concomitant reduction in beta 1- and beta 2-adrenoceptor function related to the degree of heart failure in patients with mitral valve disease
    • Brodde, O. E.; Zerkowski, H. R.; Doetsch, N.; Motomura, S.; Khamssi, M.; Michel, M. C. Myocardial beta-adrenoceptor changes in heart failure: concomitant reduction in beta 1- and beta 2-adrenoceptor function related to the degree of heart failure in patients with mitral valve disease. J. Am. Coll. Cardiol. 1989, 14, 323-331.
    • (1989) J. Am. Coll. Cardiol. , vol.14 , pp. 323-331
    • Brodde, O.E.1    Zerkowski, H.R.2    Doetsch, N.3    Motomura, S.4    Khamssi, M.5    Michel, M.C.6
  • 3
    • 0026689448 scopus 로고
    • Chronic beta 1-blocker treatment and cardiac beta 2-adrenoceptor function
    • Brodde, O. E. Chronic beta 1-blocker treatment and cardiac beta 2-adrenoceptor function [letter]. Am. Heart J. 1992, 123, 1727-1728.
    • (1992) Am. Heart J. , vol.123 , pp. 1727-1728
    • Brodde, O.E.1
  • 4
    • 0024338393 scopus 로고
    • Drug- and disease-induced changes of human cardiac beta-1 and beta-2 adrenoceptors
    • Brodde, O. E.; Zerkowski, H. R.; Borst, H. G.; Maier, W.; Michel, M. C. Drug- and disease-induced changes of human cardiac beta-1 and beta-2 adrenoceptors. Eur. Heart J. 1989, 10 (Suppl. B), 38-44.
    • (1989) Eur. Heart J. , vol.10 , Issue.SUPPL. B , pp. 38-44
    • Brodde, O.E.1    Zerkowski, H.R.2    Borst, H.G.3    Maier, W.4    Michel, M.C.5
  • 5
    • 0022980843 scopus 로고
    • Beta 1- and beta 2-adrenergic-receptor subpopulations in nonfailing and failing human ventricular myocardium: Coupling of both receptor subtypes to muscle contraction and selective beta 1- receptor down-regulation in heart failure
    • Bristow, M. R.; Ginsburg, R.; Umans, V.; Fowler, M.; Minobe, W.; Rasmussen, R.; Zera, P.; Menlove, R.; Shah, P.; Jamieson, S. Beta 1- and beta 2-adrenergic-receptor subpopulations in nonfailing and failing human ventricular myocardium: coupling of both receptor subtypes to muscle contraction and selective beta 1- receptor down-regulation in heart failure. Circ. Res. 1986, 59, 297-309.
    • (1986) Circ. Res. , vol.59 , pp. 297-309
    • Bristow, M.R.1    Ginsburg, R.2    Umans, V.3    Fowler, M.4    Minobe, W.5    Rasmussen, R.6    Zera, P.7    Menlove, R.8    Shah, P.9    Jamieson, S.10
  • 6
    • 0021856658 scopus 로고
    • Beta-adrenergic function in heart muscle disease and heart failure
    • Bristow, M. R.; Kantrowitz, N. E.; Ginsburg, R.; Fowler, M. B. Beta-adrenergic function in heart muscle disease and heart failure. J. Mol. Cell Cardiol. 1985, 17 (Suppl. 2), 41-52.
    • (1985) J. Mol. Cell Cardiol. , vol.17 , Issue.2 SUPPL. , pp. 41-52
    • Bristow, M.R.1    Kantrowitz, N.E.2    Ginsburg, R.3    Fowler, M.B.4
  • 9
    • 0025877113 scopus 로고
    • Asymmetric synthesis of a precursor for the automated radiosynthesis of S-(3′-t-butylamino-2′-hydroxypropoxy)- benzimidazol-2-[11C]one (S-[11C]CGP 12177) as a preferred radioligand for beta-adrenergic receptors
    • Brady, F.; Luthra, S. K.; Tochon Danguy, H. J.; Steel, C. J.; Waters, S. L.; Kensett, M. J.; Landais, P.; Shah, F.; Jaeggi, K. A.; Drake, A.; et al. Asymmetric synthesis of a precursor for the automated radiosynthesis of S-(3′-t-butylamino-2′-hydroxypropoxy)- benzimidazol-2-[11C]one (S-[11C]CGP 12177) as a preferred radioligand for beta-adrenergic receptors. Int. J. Radiat. Appl. Instrum. A 1991, 42, 621-628.
    • (1991) Int. J. Radiat. Appl. Instrum. A , vol.42 , pp. 621-628
    • Brady, F.1    Luthra, S.K.2    Tochon Danguy, H.J.3    Steel, C.J.4    Waters, S.L.5    Kensett, M.J.6    Landais, P.7    Shah, F.8    Jaeggi, K.A.9    Drake, A.10
  • 10
    • 0019196310 scopus 로고
    • Antagonist dissociation constants and relative agonist efficacies for compounds interacting with beta-1 and beta-2 adrenergic receptors in the rat jugular vein
    • Cohen, M. L.; Ruffolo, R. R.; Wiley, K. S. Antagonist dissociation constants and relative agonist efficacies for compounds interacting with beta-1 and beta-2 adrenergic receptors in the rat jugular vein. J. Pharmacol. Exp. Ther. 1980, 215, 325.
    • (1980) J. Pharmacol. Exp. Ther. , vol.215 , pp. 325
    • Cohen, M.L.1    Ruffolo, R.R.2    Wiley, K.S.3
  • 11
    • 0020501917 scopus 로고
    • A comparison of the selectivity of carazolol with that of other beta-2 selective adrenoceptor antagonists
    • Costin, B. I.; O'Donnell, S. R.; Wanstall, J. C. A comparison of the selectivity of carazolol with that of other beta-2 selective adrenoceptor antagonists. J. Pharm. Pharmacol. 1983, 35, 590.
    • (1983) J. Pharm. Pharmacol. , vol.35 , pp. 590
    • Costin, B.I.1    O'Donnell, S.R.2    Wanstall, J.C.3
  • 12
    • 0018693255 scopus 로고
    • Carazolol, an extremely potent β-adrenergic blocker: Binding to β-receptors in brain membranes
    • Innis, R. B.; Correa, F. M. A.; Snyder, S. H. Carazolol, an extremely potent β-adrenergic blocker: Binding to β-receptors in brain membranes. Life Sci. 1979, 24, 2255-2264.
    • (1979) Life Sci. , vol.24 , pp. 2255-2264
    • Innis, R.B.1    Correa, F.M.A.2    Snyder, S.H.3
  • 13
    • 0017853668 scopus 로고
    • The affinity of carazolol for myocardial and tracheal β-adrenoceptors activated by (-)-isoprenaline
    • Lemoine, H.; Kaumann, A. J. The affinity of carazolol for myocardial and tracheal β-adrenoceptors activated by (-)-isoprenaline. Naunyn-Schmiedebergs Arch. Pharmacol. 1978, 302, R53.
    • (1978) Naunyn-Schmiedebergs Arch. Pharmacol. , vol.302
    • Lemoine, H.1    Kaumann, A.J.2
  • 14
    • 0022365171 scopus 로고
    • Direct labelling of beta-2-adrenoceptors. A comparison of binding potency of 3H-ICI118,-551 and blocking potency of ICI118,551
    • Lemoine, H.; Ehle, B.; Kaumann, A. J. Direct labelling of beta-2-adrenoceptors. A comparison of binding potency of 3H-ICI118,-551 and blocking potency of ICI118,551. Naunyn-Schmiedebergs Arch. Pharmacol. 1985, 331, 40..
    • (1985) Naunyn-Schmiedebergs Arch. Pharmacol. , vol.331 , pp. 40
    • Lemoine, H.1    Ehle, B.2    Kaumann, A.J.3
  • 15
    • 0019395308 scopus 로고
    • Characterization of [3H] (±) carazololbinding to β-adrenergic receptors. Application to study of β-adrenergic receptor subtypes in canine ventricular myocardium and lung
    • Manalan, A. S.; Besch, H. R.; Watanabe, A. M. Characterization of [3H] (±) carazololbinding to β-adrenergic receptors. Application to study of β-adrenergic receptor subtypes in canine ventricular myocardium and lung. Circ. Res. 1981, 49, 326.
    • (1981) Circ. Res. , vol.49 , pp. 326
    • Manalan, A.S.1    Besch, H.R.2    Watanabe, A.M.3
  • 16
    • 33544472678 scopus 로고
    • Preparation and in vivo binding of [11C]carazolol, a radiotracer for the beta-adrenergic receptor
    • Berridge, M. S.; Cassidy, E. H.; Terris, A. H.; Vesselle, J. M. Preparation and in vivo binding of [11C]carazolol, a radiotracer for the beta-adrenergic receptor. Int. J. Radiat. Appl. Instrum. B 1992, 19, 563-569.
    • (1992) Int. J. Radiat. Appl. Instrum. B , vol.19 , pp. 563-569
    • Berridge, M.S.1    Cassidy, E.H.2    Terris, A.H.3    Vesselle, J.M.4
  • 18
    • 0028150716 scopus 로고
    • Synthesis, binding properties, and 18F labeling of fluorocarazolol, a high-affinity beta-adrenergic receptor antagonist
    • Zheng, L.; Berridge, M. S.; Ernsberger, P. Synthesis, binding properties, and 18F labeling of fluorocarazolol, a high-affinity beta-adrenergic receptor antagonist. J. Med. Chem. 1994, 37, 3219-3230.
    • (1994) J. Med. Chem. , vol.37 , pp. 3219-3230
    • Zheng, L.1    Berridge, M.S.2    Ernsberger, P.3
  • 19
    • 0029990579 scopus 로고    scopus 로고
    • Pharmacological characterization in vitro and in vivo of 1231-labelled derivatives of the beta-adrenoceptor antagonist CGP12177, designed for the imaging of cardiac beta-adrenoceptors
    • in press
    • Dubois, E. A.; Somsen, G. A.; van den Bos, J. C.; Janssen, A. G. M.; Boer, G. J.; Batink, H. D.; van Royen, E. A.; Pfaffendorf, M.; van Zwieten, P. A. Pharmacological characterization in vitro and in vivo of 1231-labelled derivatives of the beta-adrenoceptor antagonist CGP12177, designed for the imaging of cardiac beta-adrenoceptors. J. Nucl. Cardiol. 1996, in press.
    • (1996) J. Nucl. Cardiol.
    • Dubois, E.A.1    Somsen, G.A.2    Van Den Bos, J.C.3    Janssen, A.G.M.4    Boer, G.J.5    Batink, H.D.6    Van Royen, E.A.7    Pfaffendorf, M.8    Van Zwieten, P.A.9
  • 20
    • 0021258642 scopus 로고
    • Different steric characteristics of beta 1- and beta 2-adrenoceptors
    • Morris, T. H.; Kaumann, A. J. Different steric characteristics of beta 1- and beta 2-adrenoceptors. Naunyn-Schmiedebergs Arch. Pharmacol. 1984, 327, 176-179.
    • (1984) Naunyn-Schmiedebergs Arch. Pharmacol. , vol.327 , pp. 176-179
    • Morris, T.H.1    Kaumann, A.J.2
  • 21
    • 0028107303 scopus 로고
    • Forskolin binding sites and G-protein immunoreactivity in rat hearts during aging
    • Shu, Y.; Scarpace, P. J. Forskolin binding sites and G-protein immunoreactivity in rat hearts during aging. J. Cardiovasc. Pharmacol. 1994, 23, 188-193.
    • (1994) J. Cardiovasc. Pharmacol. , vol.23 , pp. 188-193
    • Shu, Y.1    Scarpace, P.J.2
  • 22
    • 0000209289 scopus 로고
    • Arenesulfonate derivatives of homochiral glycidol: Versatile chiral building-blocks for organic synthesis
    • Klunder, J. M.; Onami, T.; Sharpless, K. B. Arenesulfonate derivatives of homochiral glycidol: versatile chiral building-blocks for organic synthesis. J. Org. Chem. 1989, 54, 1295-1304.
    • (1989) J. Org. Chem. , vol.54 , pp. 1295-1304
    • Klunder, J.M.1    Onami, T.2    Sharpless, K.B.3
  • 23
    • 10144226195 scopus 로고
    • Verfahren zur Herstellung von 4-hydroxycarbazol
    • Ger. Offen DE 2928483, Boehringer Mannheim GmbH, Germany
    • Lauer, K.; Kiegel, E. Verfahren zur Herstellung von 4-hydroxycarbazol. (A method for the synthesis of 4-hydroxycarbazole.) Ger. Offen DE 2928483, Boehringer Mannheim GmbH, Germany; Chem. Abstr. 1981, 93, 114325.
    • (1981) Chem. Abstr. , vol.93 , pp. 114325
    • Lauer, K.1    Kiegel, E.2
  • 24
    • 10144256296 scopus 로고
    • Process for the preparation of 4-keto-1,2,3,4-tetrahydrocarbazole
    • U.S. Patent No. 3892766, Warner-Lamberts Co.
    • Zinnes, H. Process for the preparation of 4-keto-1,2,3,4-tetrahydrocarbazole. U.S. Patent No. 3892766, Warner-Lamberts Co.; Chem. Abstr. 1975, 83, 178814v.
    • (1975) Chem. Abstr. , vol.83
    • Zinnes, H.1
  • 25
    • 0026513574 scopus 로고
    • S-[1-(2,3-Diaminophenoxy)]-3′-(N-t-butylamino)propan-2′-ol. Simplified asymmetric synthesis with CD and chiral HPLC analysis
    • Aigbirhio, F.; Pike, V. W.; Francotte, E.; Waters, S. L.; Banfield, B.; Jaeggi, K. A.; Drake, A. S-[1-(2,3-Diaminophenoxy)]-3′-(N-t-butylamino)propan-2′-ol. Simplified asymmetric synthesis with CD and chiral HPLC analysis. Tetrahedron: Asymmetry 1992, 3, 539-554.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 539-554
    • Aigbirhio, F.1    Pike, V.W.2    Francotte, E.3    Waters, S.L.4    Banfield, B.5    Jaeggi, K.A.6    Drake, A.7
  • 26
    • 37049069856 scopus 로고
    • Synthesis of 4-N,N-dimethyl(aminoethyl)-1,2,3,4-tetrahydrocarbazole: Molecular structure and reactivity of the 1,2-dihydrocarbazol-4(3H)-one and derivatives
    • Rodriguez, J.-G.; Temprano, F.; Esteban-Calderon, C.; Martinez-Ripoll, M. Synthesis of 4-(N,N-dimethyl(aminoethyl)-1,2,3,4-tetrahydrocarbazole: molecular structure and reactivity of the 1,2-dihydrocarbazol-4(3H)-one and derivatives. J. Chem. Soc., Perkin Trans. I 1989, 2117-2122.
    • (1989) J. Chem. Soc., Perkin Trans. I , pp. 2117-2122
    • Rodriguez, J.-G.1    Temprano, F.2    Esteban-Calderon, C.3    Martinez-Ripoll, M.4
  • 27
    • 0019732048 scopus 로고
    • (+/-)[125Iodo] cyanopindolol, a new ligand for beta- adrenoceptors: Identification and quantitation of subclasses of beta-adrenoceptors in guinea pig
    • Engel, G.; Hoyer, D.; Berthold, R.; Wagner, H. (+/-)[125Iodo] cyanopindolol, a new ligand for beta- adrenoceptors: identification and quantitation of subclasses of beta-adrenoceptors in guinea pig. Naunyn-Schmiedebergs. Arch. Pharmacol. 1981, 317, 277-285.
    • (1981) Naunyn-Schmiedebergs. Arch. Pharmacol. , vol.317 , pp. 277-285
    • Engel, G.1    Hoyer, D.2    Berthold, R.3    Wagner, H.4
  • 28
    • 0026825699 scopus 로고
    • Vinylstannylated alkylating agents as prosthetic groups for radioiodination of small molecules; Design, synthesis and application to iodoallyl analogues of spiperone and diprenorphine
    • Musachio, J. L.; Lever, J. R. Vinylstannylated alkylating agents as prosthetic groups for radioiodination of small molecules; Design, synthesis and application to iodoallyl analogues of spiperone and diprenorphine. Bioconjugate Chem. 1992, 3, 167-175.
    • (1992) Bioconjugate Chem. , vol.3 , pp. 167-175
    • Musachio, J.L.1    Lever, J.R.2


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