Biochemical and functional characterization of 1-benzyl substituted trimetoquinol affinity analogs on rat and human β-adrenoceptors

Biochemical Pharmacology

Volumn 59, Issue 5, 2000, Pages 517-529

  Mehta, Ratna C ^a   Salazar Bookaman, Margarita M ^b   Fertel, Richard H ^a   De Los Angeles, Joseph ^c   Nikulin, Victor I ^c   Fraundorfer, Paul F ^a   Miller, Duane D ^c   Feller, Dennis R ^a,d  

^a OHIO STATE UNIVERSITY   (United States)

^b UNIVERSIDAD CENTRAL DE VENEZUELA   (Venezuela)

^c UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

^d UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

3 Adrenoceptor; Adenylyl cyclase; Affinity labels; Chinese hamster ovary cells; Radioligand binding; Tetrahydroisoquinolines

Indexed keywords

3',4' DIHYDROXY 2 METHYLPROPIOPHENONE; 4 [2 [[2 (3 CHLOROPHENYL) 2 HYDROXYETHYL]AMINO]PROPYL]PHENOXYACETIC ACID; ADENYLATE CYCLASE; AMINO ACID; BETA 3 ADRENERGIC RECEPTOR; BETA ADRENERGIC RECEPTOR; CARBACHOL; CYCLIC AMP; CYSTEINE; FUNCTIONAL GROUP; GLUTATHIONE; ISOPRENALINE; LYSINE; PARTIAL AGONIST; PHENTOLAMINE; PHENYLEPHRINE; PINDOLOL; PROPRANOLOL; RADIOLIGAND; TRETOQUINOL; TRETOQUINOL DERIVATIVE;

AFFINITY LABELING; ALLOSTERISM; ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BINDING COMPETITION; CHO CELL; CHRONOTROPISM; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG SELECTIVITY; ENZYME ACTIVATION; ESOPHAGUS; HEART ATRIUM; HUMAN; HYDROPHOBICITY; NONHUMAN; PRIORITY JOURNAL; RADIOASSAY; RAT; RECEPTOR BINDING; SMOOTH MUSCLE CONTRACTILITY; STRUCTURE ACTIVITY RELATION; TRACHEA;

ADRENERGIC BETA-AGONISTS; ANIMALS; AORTA; ATRIAL FUNCTION, RIGHT; BINDING, COMPETITIVE; CHO CELLS; CRICETINAE; CYCLIC AMP; HUMANS; RATS; RECEPTORS, ADRENERGIC, BETA; RECEPTORS, ADRENERGIC, BETA-3; TRETOQUINOL;

EID: 0033954448     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(99)00376-7     Document Type: Article

References (50)

1. Strosberg A.D. Structure, function and regulation of the three β-adrenoceptor subtypes. Ruffolo R.R. Jr, Hollinger M.A. G-Protein Coupled Transmembrane Signaling Mechanisms. 1995;35-56 CRC Press, Boca Raton.
2. Strader C.D., Fong T.M., Candelore M.C., Cascieri M.A., Weinberg D., Bayne M. Adrenergic receptors as models for the family of G protein coupled receptors. Ruffolo R.R. Jr). Adrenoceptors Structure, Function and Pharmacology . 1995;195-202 Harwood Academic Publishers, Luxembourg.
3. Lands A.M., Arnold A., McAuliff J.P., Luduena F.P., Brown T.G. Differentiation of receptor systems activated by sympathomimetic amines. Nature. 214:1967;597-598.
4. Arch J.R.S., Ainsworth A.T., Cawthorne M.A., Piercy V., Sennitt M.V., Thody V.E., Wilson C., Wilson S. Atypical β-adrenoceptor on brown adipocytes as targets for antiobesity drugs. Nature. 309:1984;163-165.
5. 3-adrenergic receptors Differential agonist activation of recombinant receptors in Chinese hamster ovary cells . Mol Pharmacol. 42:1992;634-637.
6. 3-adrenergic receptor. Science. 245:1989;1118-1121.
7. Muzzin P., Revelli J.-P., Kuhne F., Gocayne J.D., McCombie W.R., Venter J.C., Giacobino J.-P., Fraser C.M. An adipose tissue-specific β-adrenergic receptor Molecular cloning and down-regulation in obesity . J Biol Chem. 266:1991;24053-24058.
8. Tate K.M., Briend-Sutren M.-M., Emorine L.J., Delavier-Klutchko C., Marullo S., Strosberg A.D. Expression of three human β-adrenergic receptor subtypes in transfected Chinese hamster ovary cells. Eur J Biochem. 196:1991;357-361.
9. 3-adrenergic receptor gene. Mol Pharmacol. 44:1994;262-270.
10. Kaumann A.J. Four β-adrenoceptor subtypes in the mammalian heart. Trends Pharmacol Sci. 18:1997;70-76.
11. 3-adrenoceptor The search for a physiological function . Trends Pharmacol Sci. 15:1994;3-7.
12. 3 adrenergic receptor? Cell Signal. 7:1995;9-15.
13. 3-adrenoceptors in human omental and mouse 3T3-L1 adipocytes. Pharmacol Toxicol. 78:1996;254-263.
14. 3 and atypical β-adrenoceptors. Med Res Rev. 13:1993;663-729.
15. 3-adrenoceptor agonists in the treatment of obesity and diabetes. Int J Obes. 20:1996;191-196.
16. 3-Adrenergic agonists. Drugs Future. 18:1993;529-549.
17. 3-adrenoceptor agonist, in yellow KK mice. Life Sci. 54:1994;491-498.
18. 3-adrenergic receptor agonist increases metabolic rate in rhesus monkeys. J Clin Invest. 101:1998;2387-2393.
19. 3-adrenoceptor in guinea-pig ileum. Gen Pharmacol. 23:1992;171-176.
20. Fletcher D.S., Candelore M.R., Grujic D., Lowell B.B., Luell S., Susulic V.S., MacIntyre D.E. Beta-3 adrenergic receptor agonists cause an increase in gastrointestinal transit time in wild-type mice, but not in mice lacking the beta-3 adrenergic receptor. J Pharmacol Exp Ther. 287:1998;720-724.
21. Bianchetti A., Manara L. In vitro inhibition of intestinal motility by phenylethanol-aminotetralines Evidence of atypical β-adrenoceptors in rat colon . Br J Pharmacol. 100:1990;831-839.
22. Iwasawa Y., Kiyomoto A. Studies on tetrahydroisoquinolines (THI). (I) Bronchodilator activity and structure-activity relationship. Jpn J Pharmacol. 17:1967;143-152.
23. Mukhopadhyay A., Sober D.J., Chang J., Slenn R.T., Amin H.M., Miller D.D., Feller D.R. Bronchoselective actions of a new series of trimetoquinol analogues. Eur J Pharmacol. 77:1982;209-219.
24. Feller D.R., Piascik M.T., Miller D.D. Activation of adrenoceptors and adenylate cyclase in adipocytes by catecholamines and tetrahydroisoquinolines. Szabadi E., Bradshaw C.M., Bevan P. Recent Advances in the Pharmacology of Adrenoceptors. 1978;111-120 Elsevier, New York.
25. Fraundorfer P, Functional and biochemical characterization of trimetoquinol (TMQ) analog interactions with β-adrenergic receptor subtypes. Ph.D. Dissertation. The Ohio State University, Columbus, OH, 1993.
26. Dixon R.A.F., Sigal I.S., Strader C.D. Structure-function analysis of the β-adrenergic receptor. Cold Spring Harb Symp Quant Biol. 53:1988;487-497.
27. Strader C.D., Sigal I.S., Register R.B., Candelore M.R., Rands E., Dixon R.A.F. Identification of residues required for ligand binding to the β-adrenergic receptor. Proc Natl Acad Sci USA. 84:1987;4384-4388.
28. Strader C.D., Candelore M.R., Hill W.S., Sigal I.S., Dixon R.A.F. Identification of two serine residues involved in agonist activation of the β-adrenergic receptor. J Biol Chem. 264:1989;13572-13578.
29. Konkar A.A., Fraundorfer P.F., Fertel R.H., Burkman A.M., Miller D.D., Feller D.R. Pharmacological activities of trimetoquinol and 1-benzyl halogen-substituted analogues on rat β-adrenoceptor subtypes. Eur J Pharmacol. 305:1996;63-71.
30. 3H]CGP-12177, generally classified as an antagonist, is a thermogenic agonist in brown adipose tissue. Biochem J. 261:1989;401-405.
31. Sugasawa T., Matsuzaki M., Morooka S., Foignant N., Blin N., Strosberg A.D. In vitro study of a novel atypical β-adrenoceptor agonist, SM-11044. Eur J Pharmacol. 216:1992;207-215.
32. 3-adrenergic receptor. Mol Pharmacol. 44:1993;1094-1104.
33. Lezama E.J., Konkar A.A., Salazar-Bookaman M.M., Miller D.D., Feller D.R. Pharmacological study of atypical β-adrenoceptors in rat esophageal smooth muscle. Eur J Pharmacol. 308:1996;69-80.
34. 125Iodo]cyanopindolol, a new ligand for β-adrenoceptors Identification and quantitation of subclasses of β-adrenoceptors in guinea pig . Naunyn Schmiedebergs Arch Pharmacol. 317:1981;277-285.
35. Brooker G., Harper J.F., Terasaki W.L., Moylan R.D. Radioimmunoassay of cyclic AMP and cyclic GMP. Adv Cyclic Nucleotide Res. 10:1979;1-33.
36. Fraundorfer P.F., Fertel R.H., Miller D.D., Feller D.R. Biochemical and pharmacological characterization of high-affinity trimetoquinol analogs on guinea pig and human beta adrenergic receptor subtypes Evidence for partial agonism . J Pharmacol Exp Ther. 270:1994;665-674.
37. Lowry O.H., Rosebrough N.J., Farr A.L., Randall R.J. Protein measurement with the Folin phenol reagent. J Biol Chem. 193:1951;265-275.
38. Staff of the Department of Pharmacology, University of Edinburgh, In: Pharmacological Experiments on Isolated Preparations, pp. 96-99. Livingstone, Limited, London, 1968.
39. van Rossum J.M. Cumulative dose-response curves. II. Technique for the making of dose-response curves in isolated organs and the evaluation of drug parameters. Arch Int Pharmacodyn Ther. 143:1963;299-330.
40. 50) of an enzymatic reaction. Biochem Pharmacol. 22:1973;3099-3108.
41. Furchgott R.F., Bursztyn P. Comparison of dissociation constants and relative efficacies of selected compounds acting on parasympathetic receptors. Ann NY Acad Sci. 144:1967;882-889.
42. 3-adrenoceptor agonists . J Med Chem. 42:1999;2287-2294.
43. Sweet F., Murdock G.L. Affinity labeling of hormone-specific proteins. Endocr Rev. 8:1987;154-184.
44. Triggle D.J. 2-Halogenoethylamines and receptor analysis. Adv Drug Res. 2:1965;173-189.
45. Jørgensen P.L., Karlish S.J.D., Gitler C. Evidence for the organization of the transmembrane segments of (Na,K)-ATPase based on labeling lipid-embedded and surface domains of the α-subunit. J Biol Chem. 257:1982;7435-7442.
46. Johnson M., Butchers P.R., Coleman R.A., Nials A.T., Strong P., Sumner M.J., Vardey C.J., Whelan C.J. The pharmacology of salmeterol. Life Sci. 52:1993;2131-2143.
47. Strosberg A.D., Camoin L., Blin N., Maigret B. In receptors coupled to GTP-binding proteins, ligand binding and G-protein activation is a multistep dynamic process. Drug Des Discov. 9:1993;199-211.
48. 3-adrenoceptor. Trends Pharmacol Sci. 17:1996;373-381.
49. 3-adrenoceptor Transmembrane residues involved in ligand binding and signal transduction . Eur J Biochem. 251:1998;590-596.
50. 2-adrenergic receptor ligand binding pocket. Mol Pharmacol. 49:1996;1021-1032.