Stereochemical basis for a unified structure activity theory of aromatic and heterocyclic rings in selected opioids and opioid peptides

Perspectives in Medicinal Chemistry

Volumn 2010, Issue 4, 2010, Pages 1-10

  Goldberg, Joel S ^a  

^a DUKE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Analgesic; Heterocyclic; Opioid; Stereochemistry

Indexed keywords

ALANINE; ALVIMOPAM; FENTANYL; GLYCINE; HETEROCYCLIC COMPOUND; METHADONE; MORPHINE; NALOXONE; NALTREXONE; OPIATE; OPIATE PEPTIDE; PETHIDINE; PROLINE; TYROSINE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANALGESIC ACTIVITY; ARTICLE; DRUG POTENCY; DRUG STRUCTURE; HUMAN; IN VIVO STUDY; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 77953380678     PISSN: None     EISSN: 1177391X     Source Type: Journal    
DOI: 10.4137/pmc.s3898     Document Type: Article

References (35)

1. Fürst S, Hosztafi S. The chemical and pharmacological importance of morphine analogues. Acta Physiol Hung. 2008 Mar;95(1):3-44. Review.
2. Janecka A, Perlikowska R, Gach K, Wyrebska A, Fichna J. Development of Opioid Peptide Analogs for Pain Relief. Curr Pharm Des. 2009 Dec 23.
3. Beckett AH, Casy AF. Stereochemistry of certain analgesics. Nature. 1954 Jun 26;173(4417):1231-2.
4. Beckett AH, Casy AF. Synthetic analgesics: stereochemical considerations. J Pharm Pharmacol. 1954 Dec;6(12):986-1001.
5. Kane BE, Svensson B, Ferguson DM. Molecular recognition of opioid receptor ligands peridyl)-N-phenylpropanamide and N-(3-methyl-1-(1- methyl-2-phenylethyl)-4-piperidyl)-N-phenylpropanamide. J Med Chem. 1974 Oct;17(10):1047-51.
6. Cometta-Morini C, Maguire PA, Loew GH. Molecular determinants of mu receptor recognition for the fentanyl class of compounds. Mol Pharmacol. 1992 Jan;41(1):185-96.
7. Patrick, Graham L. An introduction to medicinal chemistry, Oxford University Press 1995; p. 264-5.
8. Takemori AE, Portoghese PS. Eur J Pharmacol. Comparative antagonism by naltrexone and naloxone of mu, kappa, and delta agonists. 1984 Sep 3;104(1-2):101-4.
9. Gero A. Steric Considerations on the Chemical Structure and Physiological Activity of Methadone and Related Compounds. Science. 1954 Jan 22;119(3082):112-4.
10. Pauling, Linus: The nature of the chemical bond, Cornell University Press (1960).
11. Sullivan HR, Due SL, McMahon RE. The difference in activity between (+)- and (-)-methadone is intrinsic and not due to a difference in metabolism. J Pharm Pharmacol. 1975 Oct;27(10):728-32.
12. Duax WL, Smith GD, Griffin JF, Portoghese PS. Methadone conformation and opioid activity. Science. 1983 Apr 22;220(4595):417-8.
13. Loew GH, Berkowitz DS, Newth RC. Quantum chemical studies of methadone. J Med Chem. 1976 Jul;19(7):863-9.
14. Henkel JG, Bell KH, Portoghese PS. Stereochemical studies on medicinal agents. 16. Conformational studies of methadone and isomethadone utilizing circular dichroism and proton magnetic resonance. J Med Chem. 1974 Jan;17(1):124-9.
15. Martin J, Andrews P. Conformation-activity relationships of opiate analgesics. J Comput Aided Mol Des. 1987 Apr;1(1):53-72.
16. Klein CL, Stevens ED, Fifer EK, Borne RF. Molecular structure of two conformationally restrained fentanyl analogues: cis-and trans-isomers of N-(3-methyl-1-[2-(1,2,3,4-tetrahydro)naphthyl]-4-piperidinyl)-N-phenylpropanamide. J Pharm Sci. 1985 Nov; 74(11):1147-51.
17. Peptides with opioid activity www.lycaeum.org/drugs/Peptides/opioidpeptides.html
18. Vass E, Hollósi M, Kveder M, Kojić-Prodić B, Cudić MB, Horvat S. Spectroscopic evidence of beta-turn in N-glycated peptidomimetics related to leucine-enkephalin. Spectrochim Acta A Mol Biomol Spectrosc. 2000 Nov 1;56A(12):2479-89.
19. Ishida T, Kenmotsu M, Mino Y, et al. X-ray diffraction studies of enkephalins. Crystal structure of [(4'-bromo)Phe4,Leu5]enkephalin. Biochem J. 1984 Mar 15;218(3):677-89.
20. Blomberg D, Hedenström M, Kreye P, Sethson I, Brickmann K, Kihlberg J. Synthesis and conformational studies of a beta-turn mimetic incorporated in Leu-enkephalin. J Org Chem. 2004 May 14;69(10):3500-8.
21. Choh Hao Li, United States Patent 4,317,770, D-amino acid analogs of beta-endorphin, March 2, 1982.
22. Loew GH, Burt SK. Energy conformation study of Met-enkephalin and its D-Ala2 analogue and their resemblance to rigid opiates. Proc Natl Acad Sci U S A. 1978 Jan;75(1):7-11.
23. Guzevatykh LS, Voronina TA, Emel'ianova TG, et al. [Analgesic activity of dipeptide Tyr-Pro] [Article in Russian] Izv Akad Nauk Ser Biol. 2008 Jan-Feb;(1):61-7.
24. Jaba IM, Vasincu D, Manolidis G, Haulicǎ I, Mungiu OC. Experimental data regarding the implications of certain minimum structure enkephalinlike peptides in nociceptive processing. Rom J Physiol. 2004 Jan-Jun; 41(1-2):119-26.
25. Pawar M, Kumar P, Sunkaraneni S, Sirohi S, Walker EA, Yoburn BC. Opioid agonist efficacy predicts the magnitude of tolerance and the regulation of mu-opioid receptors and dynamin-2. Eur J Pharmacol. 2007 Jun 1;563(1-3):92-101.
26. Senderowitz H, Marantz Y. G Protein-Coupled Receptors: target-based in silico screening. Curr Pharm Des. 2009;15(35):4049-68.
27. Li Y, Chase AR, Slivka PF, Baggett CT, Zhao TX, Yin H. Design, synthesis, and evaluation of biotinylated opioid derivatives as novel probes to study opioid pharmacology. Bioconjug Chem. 2008 Dec;19(12):2585-9.
28. Zhou T, Huang D, Caflisch A. Quantum Mechanical Methods for Drug Design. Curr Top Med Chem. 2009 Nov 23.
29. Dailey MM, Hait C, Holt PA, et al. Structure-based drug design: from nucleic acid to membrane protein targets. Exp Mol Pathol. 2009 Jun;86(3):141-50. Epub 2009 Jan 31. Review.
30. Pogozheva ID, Przydzial MJ, Mosberg HI. Homology modeling of opioid receptor-ligand complexes using experimental constraints. AAPS J. 2005 Oct 5;7(2):E434-48. Review.
31. Hutchinson MR, Zhang Y, Shridhar M, et al. Evidence that opioids may have toll-like receptor 4 and MD-2 effects. Brain Behav Immun. 2010 Jan;24(1):83-95. Epub 2009 Aug 11.
32. Lopes SC, Soares CM, Baptista AM, Goormaghtigh E, Cabral BJ, Castanho MA. Conformational and orientational guidance of the analgesic dipeptide kyotorphin induced by lipidic membranes: putative correlation toward receptor docking. J Phys Chem B. 2006 Feb 23;110(7):3385-94.
33. Tzschentke TM, Jahnel U, Kogel B, et al. Tapentadol hydrochloride: a nextgeneration, centrally acting analgesic with two mechanisms of action in a single molecule. Drugs Today (Barc). 2009 Jul;45(7):483-96. Review.
34. Borics A, Tóth G. Structural comparison of mu-opioid receptor selective peptides confirmed four parameters of bioactivity. J Mol Graph Model. 2009 Dec 3.
35. Vucković S, Prostran M, Ivanović M, et al. Fentanyl analogs: structureactivity- relationship study. Curr Med Chem. 2009;16(19):2468-74. Review.