Correction of the stereochemical assignment of the benzilic acid center in (R)-(-)-3-quinuclidinyl (S)-(+)-4-iodobenzilate [(R,S)-4-IQNB]

Applied Radiation and Isotopes

Volumn 48, Issue 4, 1997, Pages 463-467

  Zeeberg, Barry R ^a   Boulay, Sheila F ^a   Gitler, Miriam S ^a   Sood, Virendar K ^a   Reba, Richard C ^a,b  

^a GEORGE WASHINGTON UNIVERSITY MEDICAL CENTER   (United States)

^b UNIVERSITY OF CHICAGO MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INORGANIC ACIDS; IODINE COMPOUNDS;

BENZILIC ACID CENTERS; RADIOIODINATION; STEREOCHEMISTRY;

RADIOACTIVE TRACERS;

3 QUINUCLIDINYL 4 IODOBENZILATE; IODINE 123;

ANIMAL EXPERIMENT; ARTICLE; BRAIN; CONTROLLED STUDY; DRUG UPTAKE; PRIORITY JOURNAL; RAT; SCINTILLATION COUNTING; STEREOCHEMISTRY;

ANIMALS; BRAIN; IODINE RADIOISOTOPES; MALE; MUSCARINIC ANTAGONISTS; QUINUCLIDINYL BENZILATE; RATS; RATS, SPRAGUE-DAWLEY; STEREOISOMERISM;

EID: 0031127618     PISSN: 09698043     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8043(96)00290-4     Document Type: Article

References (19)

1. 125I]IQNB to rat brain muscarinic receptors in vivo. Nucl. Med. Biol. 23, 211.
2. Brimblecombe, R. W., Green, D. M., Inch, T. D. and Thompson, P. B. J. (1971) The significance of differences in the potency of enantiomers of anti-acetylcholine drugs. J. Pharm. Pharmac. 21, 745.
3. Cohen, V. I., Jin, B., Gitler, M. S., de la Cruz, R. A., Boulay, S. F., Sood, V. K., Zeeberg, B. R. and Reba, R. C. (1995) Novel potent and m2-selective antimuscarinic compounds which penetrate the blood brain barrier. Eur. J. Med. Chem. 30, 61.
4. 125I]iodophenyl)-α-phenyl acetate as potential radiopharmaceuticals. J. Pharmac. Sci. 78, 833.
5. Eckelman, W. C., Eng, R., Rzeszotarski, W. J., Gibson, R. E., Francis, B. and Reba, R. C. (1985) Use of 3-quinuclidinyl 4-iodobenzilate as a receptor binding radiotracer. J. Nucl. Med. 26, 637.
6. Eckelman, W. C., Reba, R. C., Rzeszotarski, W. J., Gibson, R. E., Hill, T., Holman, B. C., Budinger, T., Conklin, J. J., Eng, R. and Grissom, M. P. (1984) External imaging of cerebral muscarinic acetylcholine receptors. Science 223, 291.
7. Gibson, R. E., Weckstein, D. J., Jagoda, E. M., Rzeszotarski, W. J., Reba, R. C. and Eckelman, W. C. (1984) The characteristics of I-125 4-IQNB and H-3 QNB in vivo and in vitro. J. Nucl. Med. 25, 214.
8. 125I]IQNB. Brain Res. 687, 71.
9. Hiramatsu, Y., Eckelman, W. C. and Baum, B. J. (1994) Interaction of iodinated quinuclidinyl benzilate enantiomers with M3 muscarinic receptors. Life Sci. 54, 1777.
10. Hiramatsu, Y., Eckelman, W. C., Carrasquillo, J. A., Miletich, R. S., Valdez, I. H., Kurrasch, R. H. M., Macynski, A. A., Paik, C. H., Neumann, R. D. and Baum, B. J. (1995) Kinetic analysis of muscarinic receptors in human brain and salivary gland in vivo. Am. J. Physiol. 268, R1491.
11. Inch, T. D., Green, D. M. and Thompson, P. B. J. (1973) The central and peripheral activities of anti-acetylcholine drugs. Some concepts of practical relevance. J. Pharm. Pharmac. 25, 359.
12. Kiesewetter, D. O. (1993) Asymmetric synthesis of benzilic acid analogues using 8-phenylmenthol as a chiral auxiliary. Tetrahedr. Assym. 4, 2183.
13. 125I]IQNB. J. Label. Comp. Radiopharm. 37, 686.
14. Kiesewetter, D. O., Silverton, J. V. and Eckelman, W. C. (1994) Stereoselective synthesis of [R,R]IQNB and fluoroalkyl analogs of QNB (abstract). J. Label. Comp. Radiopharm. 35, 419.
15. Li, M., Yasuda, R. P., Wall, S. J., Wellstein, A. and Wolfe, B. (1991) Distribution of m2 muscarinic receptors in rat brain using antisera selective for m2 receptors. Molec. Pharmac. 40, 28.
16. Rzeszotarski, W. J., Eckelman, W. C., Francis, B. E., Simms, D. A., Gibson, R. E., Jagoda, E. M., Grissom, M. P., Eng, R. R., Conklin, J. J. and Reba, R. C. (1984) Synthesis and evaluation of radioiodinated derivatives of 1-azabicyclo[2.2.2]ocy-3-yl α-hydroxy-α-phenylacetate as potential radiopharmaceuticals. J. Med. Chem. 27, 156.
17. Wall, S. J., Yasuda, R. P., Hory, F., Flagg, S., Martin, B. M., Ginns, E. I. and Wolfe, B. B. (1991a) Production of antisera selective for m1 muscarinic receptors using fusion proteins: distribution of m1 receptors in rat brain. Molec. Pharmac. 39, 643.
18. Wall, S. J., Yasuda, R. P., Li, M. and Wolfe, B. B. (1991b) Development of an antiserum against m3 muscarinic receptors: distribution of m3 receptors in rat tissues and clonal cell lines. Molec. Pharmac. 40, 783.
19. Yasuda, R. P., Ciesla, W., Flores, L. R., Wall, S. J., Li, M., Satkus, S. A., Weisstein, J. S., Spagnola, B. V. and Wolfe, B. B. (1993) Development of antisera selective for m4 and m5 muscarinic cholinergic receptors: distribution of m4 and m5 receptors in rat brain. Molec. Pharmac. 43, 149.