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Volumn 40, Issue 1, 1997, Pages 117-124

Stereoselective synthesis and biodistribution of potent [11C]-labeled antagonists for positron emission tomography imaging of muscarinic receptors in the airways

Author keywords

[No Author keywords available]

Indexed keywords

ADRENERGIC RECEPTOR STIMULATING AGENT; ATROPINE; CARBON 11; CHOLINERGIC RECEPTOR BLOCKING AGENT; MUSCARINIC RECEPTOR BLOCKING AGENT; N METHYLPIPERIDIN 4 YL 2 CYCLOHEXYL 2 HYDROXY 2 PHENYLACETATE METHIODIDE; N METHYLQUINUCLIDINYL BENZILATE; QUINUCLIDIN 3 YL 2 CYCLOHEXYL 2 HYDROXYPHENYLACETATE METHIODIDE; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

EID: 0031023359     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960374w     Document Type: Article
Times cited : (20)

References (42)
  • 1
    • 0024437944 scopus 로고
    • Muscarinic receptor subtypes. Physiologic and clinical implications
    • Goyal R. Muscarinic receptor subtypes. Physiologic and clinical implications. N. Engl. J. Med. 1989, 321, 1022-1028.
    • (1989) N. Engl. J. Med. , vol.321 , pp. 1022-1028
    • Goyal, R.1
  • 2
    • 0024507616 scopus 로고
    • Antagonist binding properties of five cloned muscarinic receptors expressed in CHO-K1 cells
    • Buckley, N. J.; Bonner, T. I.; Buckley, C. M.; Brann, M. R. Antagonist binding properties of five cloned muscarinic receptors expressed in CHO-K1 cells. Mol. Pharmacol. 1989, 35, 469-476.
    • (1989) Mol. Pharmacol. , vol.35 , pp. 469-476
    • Buckley, N.J.1    Bonner, T.I.2    Buckley, C.M.3    Brann, M.R.4
  • 3
    • 0027208248 scopus 로고
    • Muscarinic receptors, characterization, coupling and function
    • Caulfield, M. P. Muscarinic receptors, characterization, coupling and function. Pharmacol. Ther. 1993, 58, 319-380.
    • (1993) Pharmacol. Ther. , vol.58 , pp. 319-380
    • Caulfield, M.P.1
  • 4
    • 0025572697 scopus 로고
    • Characterization of muscarinic M4 binding sites in rabbit lung, chicken heart and NG108-15 cells
    • Lazareno, S.; Buckley, N. J.; Roberts, F. F. Characterization of muscarinic M4 binding sites in rabbit lung, chicken heart and NG108-15 cells. Mol. Pharmacol. 1990, 38, 805-815.
    • (1990) Mol. Pharmacol. , vol.38 , pp. 805-815
    • Lazareno, S.1    Buckley, N.J.2    Roberts, F.F.3
  • 5
    • 0027509977 scopus 로고
    • Muscarinic receptor subtypes in airways
    • Barnes, P. J. Muscarinic receptor subtypes in airways. Life Sci. 1993, 52, 521-527.
    • (1993) Life Sci. , vol.52 , pp. 521-527
    • Barnes, P.J.1
  • 6
    • 0019314672 scopus 로고
    • Increased pulmonary α-adrenergic and reduced β-andrenergic receptors in experimental asthma
    • Barnes, P. J.; Dollery, C. T.; MacDermot, J. Increased pulmonary α-adrenergic and reduced β-andrenergic receptors in experimental asthma. Nature 1980, 285, 569-571.
    • (1980) Nature , vol.285 , pp. 569-571
    • Barnes, P.J.1    Dollery, C.T.2    MacDermot, J.3
  • 7
    • 0021330122 scopus 로고
    • Muscarinic cholinergic receptors in pheripheral lung tissue of normal subjects and of patients with chronic obstructive lung disease
    • Raaijmakers, J. A. M.; Terpstra. G. K.; Van Rozen, A. J.; Witter, A.; Kreukniet, J. Muscarinic cholinergic receptors in pheripheral lung tissue of normal subjects and of patients with chronic obstructive lung disease. Clin. Sci. 1983, 66, 585-590.
    • (1983) Clin. Sci. , vol.66 , pp. 585-590
    • Raaijmakers, J.A.M.1    Terpstra, G.K.2    Van Rozen, A.J.3    Witter, A.4    Kreukniet, J.5
  • 9
    • 0039354357 scopus 로고
    • New peripheral muscarinic receptor ligands N-[F-18] fluoroethyl-QNB and -TRB for parasympathetic imaging
    • abstract
    • Mulholland, G. K.; Chin, F. I. N.; Hutchins, G. D.; Fain, R.; Zipes, D.; New peripheral muscarinic receptor ligands N-[F-18] fluoroethyl-QNB and -TRB for parasympathetic imaging. J. Nucl. Med. 1995, 36, 137P-138P (abstract).
    • (1995) J. Nucl. Med. , vol.36
    • Mulholland, G.K.1    Chin, F.I.N.2    Hutchins, G.D.3    Fain, R.4    Zipes, D.5
  • 11
    • 6744239598 scopus 로고
    • Quantification of regional cerebral muscarinic receptors in brain with the use of C11 tropanyl benzilate and positron emission tomography
    • Frey, K. A.; Koeppe, R. A.; Mulholland, G. K.; Kühl, D. E. Quantification of regional cerebral muscarinic receptors in brain with the use of C11 tropanyl benzilate and positron emission tomography. J. Nucl. Med. 1990, 31, 779.
    • (1990) J. Nucl. Med. , vol.31 , pp. 779
    • Frey, K.A.1    Koeppe, R.A.2    Mulholland, G.K.3    Kühl, D.E.4
  • 12
    • 0023818824 scopus 로고
    • 3H]-Quinuclidinyl benzilate binding to the human lung muscarinic receptor
    • 3H]-Quinuclidinyl benzilate binding to the human lung muscarinic receptor. Biochem. Pharmacol. 1988, 37, 973-976.
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 973-976
    • Joad, P.J.1    Casale, T.B.2
  • 13
    • 0024371807 scopus 로고
    • Muscarinic subtypes in human and guinea pig lung
    • Mak, J. W. C.; Barnes, P. J. Muscarinic subtypes in human and guinea pig lung. Eur. J. Pharmacol. 1989, 164, 223-230.
    • (1989) Eur. J. Pharmacol. , vol.164 , pp. 223-230
    • Mak, J.W.C.1    Barnes, P.J.2
  • 14
    • 0023789604 scopus 로고
    • Characterization of muscarinic receptor subtypes on human peripheral lung
    • Casale, T. B.; Ecklund, P. Characterization of muscarinic receptor subtypes on human peripheral lung. J. Appl. Physiol. 1988, 65 (2), 594-600.
    • (1988) J. Appl. Physiol. , vol.65 , Issue.2 , pp. 594-600
    • Casale, T.B.1    Ecklund, P.2
  • 18
    • 0026080473 scopus 로고
    • Binding affinities of hexahydrodifenidol and hexahydrosiladifenidol analogues at four muscarinic receptor subtypes: Constitutional and stereochemical aspects
    • Waelbroeck, M.; Camus, J.; Tastenoy, M.; Mutschier, E.; Strohmann, C.; Tacke, R.; Lambrecht, G.; Christophe, J. Binding affinities of hexahydrodifenidol and hexahydrosiladifenidol analogues at four muscarinic receptor subtypes: constitutional and stereochemical aspects. Eur. J. Pharmacol. 1991, 206, 95-103.
    • (1991) Eur. J. Pharmacol. , vol.206 , pp. 95-103
    • Waelbroeck, M.1    Camus, J.2    Tastenoy, M.3    Mutschier, E.4    Strohmann, C.5    Tacke, R.6    Lambrecht, G.7    Christophe, J.8
  • 19
    • 0027958517 scopus 로고
    • Rodent biodistribution and metabolism of tritiated 4-DAMP, a M3 subtype-selective cholinoceptor ligand
    • Van Waarde, A.; Visser, G. M.; Visser, T. J.; Brouwer, J.; Paans, M. J.; Vaalburg, W. Rodent biodistribution and metabolism of tritiated 4-DAMP, a M3 subtype-selective cholinoceptor ligand. Nucl. Med. Biol. 1994, 21, 41-47.
    • (1994) Nucl. Med. Biol. , vol.21 , pp. 41-47
    • Van Waarde, A.1    Visser, G.M.2    Visser, T.J.3    Brouwer, J.4    Paans, M.J.5    Vaalburg, W.6
  • 22
    • 0025563684 scopus 로고
    • Noninvasive quantification of muscarinic receptors in vivo with positron emission tomography in the dog heart
    • Delforge, J.; Janier, M.; Syrota, A.; Crouzel, C.; Vallois, J. M.; Cayla, J.; Lancon, J. P.; Mazoyer, B. M. Noninvasive quantification of muscarinic receptors in vivo with positron emission tomography in the dog heart. Circulation 1990, 82, 1494-1504.
    • (1990) Circulation , vol.82 , pp. 1494-1504
    • Delforge, J.1    Janier, M.2    Syrota, A.3    Crouzel, C.4    Vallois, J.M.5    Cayla, J.6    Lancon, J.P.7    Mazoyer, B.M.8
  • 23
    • 37049128268 scopus 로고
    • Asymmetric Synthesis. Part III. Stereospecific Synthesis of (R)-2-Hydroxy-2-phenylpropionic Acid, and (R)- And (S)-2-cyclohexyl-2-hydroxy-2-phenylacetic Acid Configurational relationship between (R) (-)-2-Hydroxy-2-phenylpropionic Acid and (S) (+)-2-Phenylpropionic Acid
    • Inch, T.; Ley, R. V.; Rich, P. Asymmetric Synthesis. Part III. Stereospecific Synthesis of (R)-2-Hydroxy-2-phenylpropionic Acid, and (R)- and (S)-2-cyclohexyl-2-hydroxy-2-phenylacetic Acid Configurational relationship between (R) (-)-2-Hydroxy-2-phenylpropionic Acid and (S) (+)-2-Phenylpropionic Acid. J. Chem. Soc. C 1968, 1693-1699.
    • (1968) J. Chem. Soc. C , pp. 1693-1699
    • Inch, T.1    Ley, R.V.2    Rich, P.3
  • 24
    • 0015623205 scopus 로고
    • The central and peripheral activities of anti-acetylcholine drugs. Some concepts of practical relevance
    • Inch, T. D.; Green, D. M.; Thompson, P. B. J. The central and peripheral activities of anti-acetylcholine drugs. Some concepts of practical relevance. J. Pharm. Pharmacol. 1973, 25, 359-370.
    • (1973) J. Pharm. Pharmacol. , vol.25 , pp. 359-370
    • Inch, T.D.1    Green, D.M.2    Thompson, P.B.J.3
  • 25
    • 0023007510 scopus 로고    scopus 로고
    • The absolute configuration of oxyphencyclimine, a parasympatholytic drug. Synthesis of both enantiomers
    • Schjelderup, L.; Harbitz, O.; Groth, P.; Aasen, A. J. The absolute configuration of oxyphencyclimine, a parasympatholytic drug. Synthesis of both enantiomers. Acta Chem. Scand. 1986, B40, 601-603.
    • Acta Chem. Scand. , vol.1986 B40 , pp. 601-603
    • Schjelderup, L.1    Harbitz, O.2    Groth, P.3    Aasen, A.J.4
  • 26
    • 0015621978 scopus 로고
    • Studies on the stereospecificity of closely related compounds which block postganglionic acetylcholine receptors in the guinea pig ileum
    • Barlow, R. B.; Franks, F. M.; Pearson, J. D. M. Studies on the stereospecificity of closely related compounds which block postganglionic acetylcholine receptors in the guinea pig ileum. J. Med. Chem. 1973, 16, 439-446.
    • (1973) J. Med. Chem. , vol.16 , pp. 439-446
    • Barlow, R.B.1    Franks, F.M.2    Pearson, J.D.M.3
  • 27
    • 0027378774 scopus 로고
    • Asymmetric synthesis of benzylic acid analogues using 8-phenylmenthol as a chiral auxiliary
    • Kiesewetter, D. O. Asymmetric synthesis of benzylic acid analogues using 8-phenylmenthol as a chiral auxiliary. Tetrahedron: Asymmetry 1993, 4 (10), 2183-2198.
    • (1993) Tetrahedron: Asymmetry , vol.4 , Issue.10 , pp. 2183-2198
    • Kiesewetter, D.O.1
  • 28
    • 4244000868 scopus 로고
    • Dédoublement et détermination de la configuration absolute des énantiomères de l'acide (thiényl-3)-2-cyclohexyl-2-hydroxy-2-acétique. Application à la synthèse d'esters anticholinergiques du quinuclidinol-3
    • Tambuté, A.; Collet, A. Dédoublement et détermination de la configuration absolute des énantiomères de l'acide (thiényl-3)-2-cyclohexyl-2-hydroxy-2-acétique. Application à la synthèse d'esters anticholinergiques du quinuclidinol-3. (Resolution and determination of the absolute configuration of the enantiomers of 2-(3-thienyl)-2-cyclohexyl-2-hydroxy acetic acid. Application to the synthesis of anticholinergic esters of 3-quinuclidinol.) Bull. Soc. Chim. Fr. 1984, 11, 77-82.
    • (1984) Bull. Soc. Chim. Fr. , vol.11 , pp. 77-82
    • Tambuté, A.1    Collet, A.2
  • 29
    • 0001665760 scopus 로고
    • α-Alkylation of α-hetero-substituted carboxylic acids without racemization; EPC-syntheses of tertiary alcohols and thiols
    • Seebach, D.; Naef, R.; Calderari, G. α-Alkylation of α-hetero-substituted carboxylic acids without racemization; EPC-syntheses of tertiary alcohols and thiols. Tetrahedron 1984, 40, 1313-1324.
    • (1984) Tetrahedron , vol.40 , pp. 1313-1324
    • Seebach, D.1    Naef, R.2    Calderari, G.3
  • 30
    • 0000578396 scopus 로고
    • Synthesis of enantiomerically enriched atrolactic acid and other α-hydroxy acids
    • Frater, G.; Müller, U.; Günther. W. Synthesis of enantiomerically enriched atrolactic acid and other α-hydroxy acids Tetrahedron Lett. 1981, 22, 4221-4224.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 4221-4224
    • Frater, G.1    Müller, U.2    Günther, W.3
  • 34
    • 0018690130 scopus 로고
    • Facile preparation of the enantiomers of 3-acetoxyquinuclidine and 3-quinuclidinol
    • Ringdahl, B.; Resul, B.; Dahlbom, R. Facile preparation of the enantiomers of 3-acetoxyquinuclidine and 3-quinuclidinol. Acta Pharm. Suec. 1979, 16, 281-283.
    • (1979) Acta Pharm. Suec. , vol.16 , pp. 281-283
    • Ringdahl, B.1    Resul, B.2    Dahlbom, R.3
  • 35
    • 0025751636 scopus 로고
    • Development of an antiserum against m3 muscarinic receptors: Distribution of m3 receptors in rat tissues and clonal cell lines
    • Wall, S. J.; Yasuda, R. P.; Li, M.; Wolfe, B. B. Development of an antiserum against m3 muscarinic receptors: distribution of m3 receptors in rat tissues and clonal cell lines. Mol. Pharmacol. 1991, 40, 783-789.
    • (1991) Mol. Pharmacol. , vol.40 , pp. 783-789
    • Wall, S.J.1    Yasuda, R.P.2    Li, M.3    Wolfe, B.B.4
  • 36
    • 0027466075 scopus 로고
    • Muscarinic receptors after syngeneic unilateral lung transplantation
    • Poaty, V.; Tavakoli, R.; Lockhart, A.; Frossard, N. Muscarinic receptors after syngeneic unilateral lung transplantation. Life Sci. 1993, 52, 613-620.
    • (1993) Life Sci. , vol.52 , pp. 613-620
    • Poaty, V.1    Tavakoli, R.2    Lockhart, A.3    Frossard, N.4
  • 37
    • 0021683602 scopus 로고
    • Muscarinic cholinergic receptors in developing rat lung
    • Whitsett, J. A.; Hollinger, B. Muscarinic cholinergic receptors in developing rat lung. Pediatr. Res. 1984, 18, 1136-1140.
    • (1984) Pediatr. Res. , vol.18 , pp. 1136-1140
    • Whitsett, J.A.1    Hollinger, B.2
  • 39
    • 0004149157 scopus 로고
    • Parasympathetic blocking agents. III. Phenylglycolic acid esters of N-alkyl-4-piperidinol
    • Coan, S. B.; Jaffe, B.; Papa, D. Parasympathetic blocking agents. III. Phenylglycolic acid esters of N-alkyl-4-piperidinol. J. Am. Chem. Soc. 1956, 78, 3701-3703.
    • (1956) J. Am. Chem. Soc. , vol.78 , pp. 3701-3703
    • Coan, S.B.1    Jaffe, B.2    Papa, D.3
  • 40
    • 0016177895 scopus 로고
    • Relationships between chemical structure and affinity for postganglionic acetylcholine receptors of the guinea pig ileum
    • Abramson, F. B.; Barlow, R. B.; Franks, F. M.; Pearson, J, D. M. Relationships between chemical structure and affinity for postganglionic acetylcholine receptors of the guinea pig ileum. Br. J. Pharmacol. 1974, 51, 81-93.
    • (1974) Br. J. Pharmacol. , vol.51 , pp. 81-93
    • Abramson, F.B.1    Barlow, R.B.2    Franks, F.M.3    Pearson, J.D.M.4


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