Journal Menu
- About this Journal
- Abstracting and Indexing
- Aims and Scope
- Article Processing Charges
- Articles in Press
- Author Guidelines
- Bibliographic Information
- Citations to this Journal
- Contact Information
- Editorial Board
- Editorial Workflow
- Free eTOC Alerts
- Publication Ethics
- Reviewers Acknowledgment
- Submit a Manuscript
- Subscription Information
- Table of Contents
International Journal of Medicinal Chemistry
Volume 2011 (2011), Article ID 424535, 8 pages
doi:10.1155/2011/424535
Review Article
The Discovery of Novel Selective D1 Dopaminergic Agonists: A-68930, A-77636, A-86929, and ABT-413
Global Pharmaceutical Research and Development, Martin Consulting, Waukegan, IL 60064, USA
Received 4 December 2010; Accepted 17 February 2011
Academic Editor: Hussein El-Subbagh
Copyright © 2011 Yvonne Connolly Martin. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Linked References
- O. Hornykiewicz, “Brain dopamine: A historical perspective,” Handbook of Experimental Pharmacology, vol. 154, pp. 1–22, 2002.
- J. D. Taylor, A. A. Wykes, Y. C. Gladish, and W. B. Martin, “New inhibitor of monoamine oxidase,” Nature, vol. 187, no. 4741, pp. 941–942, 1960. View at Publisher · View at Google Scholar · View at Scopus
- L. R. Swett, W. B. Martin, J. D. Taylor, G. M. Everett, A. A. Wykes, and Y. C. Gladish, “Structure-activity relations in the pargyline series,” Annals of the New York Academy of Sciences, vol. 107, pp. 891–898, 1963. View at Scopus
- Y. C. Martin, W. B. Martin, and J. D. Taylor, “The organometallic route to benzylamine type monoamine oxidase inhibitors,” Journal of Medicinal Chemistry, vol. 18, pp. 883–888, 1975.
- G. Everett, J. Davin, and J. Toman, “Pharmacological studies of monoamine oxidaseIinhibitors,” Federation Proceedings, vol. 18, p. 388, 1959.
- G. Everett and R. Weigand, “An enzyme in human blood plasma that inactivates bradykinin and kallidins,” Biochemical Pharmacology, vol. 11, no. 7, pp. 585–592, 1962. View at Scopus
- G. Everett, R. Wiegand, and W. Paton, “Central amines and behavioral states: a critique and new data,” in Proceedings of the 1st International Pharmacological Meeting, Pharmacological Analysis of Central Nervous Action 85, 1962.
- G. Everett, R. Wiegand, and F. Rinaldi, “Pharmacologic studies of some nonhydrazine mao Inhibitors,” Annals of the New York Academy of Sciences, vol. 107, no. 3, pp. 1068–1080, 1963.
- Y. C. Martin, Quantitative Drug Design: A Critical Introduction, CRC Press, Boca Raton, Fla, USA, 2nd edition, 2010.
- H. Suda, T. Takeuchi, T. Nagatsu, M. Matsuzaki, I. Matsumoto, and H. Umezawa, “Inhibition of dopamine beta-hydroxylase by 5-alkylpicolinic acid and their hypotensive effects,” Chemical and Pharmaceutical Bulletin, vol. 17, no. 11, pp. 2377–2380, 1969. View at Scopus
- L. I. Goldberg, P. F. Sonneville, and J. L. McNay, “An investigation of the structural requirements for dopamine-like renal vasodilation: phenylethylamines and apomorphine,” Journal of Pharmacology and Experimental Therapeutics, vol. 163, no. 1, pp. 188–197, 1968. View at Scopus
- L. I. Goldberg, “Cardiovascular and renal actions of dopamine: potential clinical applications,” Pharmacological Reviews, vol. 24, no. 1, pp. 1–29, 1972.
- F. N. Minard, J. C. Cain, and D. S. Grant, “Metabolism of amino acid amides of dopamine by the dog,” in Proceeding of the 165th National Meeting MEDI010, American Chemical Society Abstracts, 1973.
- F. N. Minard, J. C. Cain, D. S. Grant, C. W. Ours, and P. H. Jones, “Hydrolysis of amino acid amides of dopamine by extracts of animal tissues,” Biochemical Medicine, vol. 11, no. 4, pp. 318–326, 1974. View at Scopus
- F. N. Minard, D. S. Grant, J. C. Cain, P. H. Jones, and J. Kyncl, “Metabolism of γ-glutamyl dopamide and its carboxylic acid esters,” Biochemical Pharmacology, vol. 29, no. 1, pp. 69–75, 1980. View at Publisher · View at Google Scholar · View at Scopus
- J. Kyncl, K. Riley, Y. C. Martin, and C. W. Ours, “Upsilon-glutamyl Amide of Dopamine,” US patent no. 3,903,147, 1975.
- J. Kyncl, K. Riley, Y. C. Martin, and C. W. Ours, “Compositions and methods of increasing renal blood flow with upsilon-glutamyl amide of dopamine,” US patent no. 3,947,590, 1975.
- J. F. DeBernardis, J. J. Kyncl, F. Z. Basha et al., “Conformationally defined adrenergic agents. 2. catechol imidazoline derivatives: biological effects at α and α adrenergic receptors,” Journal of Medicinal Chemistry, vol. 29, no. 4, pp. 463–467, 1986. View at Scopus
- Y. C. Martin, E. B. Danaher, L. Kauslauskas, and K.-H. Kim, “Comparative molecular modeling of adrenergic vs. dopaminergic receptors,” in Pharmacology, M. J. Rand and C. Raper, Eds., pp. 611–614, Excerpta Medica, New York, NY, USA, 1987.
- A. A. Hancock, J. J. Kyncl, Y. C. Martin, and J. F. DeBernardis, “Differentiation of alpha-adrenergic receptors using pharmacological evaluation and molecular modeling of selective adrenergic agents,” Journal of Receptor Research, vol. 8, no. 1–4, pp. 23–46, 1988. View at Scopus
- Y. C. Martin, J. W. Kebabian, R. MacKenzie, and R. Schoenleber, “Molecular modeling-based design of novel, selective, potent D1 dopamine agonists,” in QSAR: Rational Approaches on the Design of Bioactive Compounds, C. Silipo and A. Vittoria, Eds., pp. 469–482, Elsevier, Amsterdam, The Netherlands, 1991.
- Y. C. Martin, C. T. Lin, and J. Wu., “Application of CoMFA to D1 dopaminergic agonists: a case study,” in 3D QSAR in Drug Design: Theory: Methods and Applications, H. Kubinyi, Ed., pp. 643–660, ESCOM, Leiden, The Netherlands, 1993.
- Y. C. Martin and C. T. Lin, “Multiple receptors for dopamine,” in The Practice of Medicinal Chemistry, C. G. Wermuth, Ed., pp. 459–483, Academic Press, London, UK, 1996.
- J. W. Kebabian and D. B. Calne, “Multiple receptors for dopamine,” Nature, vol. 277, no. 5692, pp. 93–96, 1979. View at Scopus
- J. W. Kebabian, “Mechanism of dopamine-mediated activation of bk channels in human coronary artery smooth muscle cells,” Advances in Experimental Medicine and Biology, vol. 235, pp. 19–31, 1988.
- B. K. Madras, M. A. Fahey, D. R. Canfield, and R. D. Spealman, “D and d dopamine receptors in caudate-putamen of nonhuman primates (macaca fascicularis),” Journal of Neurochemistry, vol. 51, no. 3, pp. 934–943, 1988. View at Scopus
- DGEOM. Distance Geometry; QCPE 590, Quantum Chemistry Program Exchange, Indiana University, Bloomington, Ind, USA, 1990.
- Y. Yuri and N. L. Allinger, “The MMP2 calculational method,” Journal of Computational Chemistry, vol. 8, pp. 581–603, 1987.
- M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart, “AM1: a new general purpose quantum mechanical molecular model,” Journal of the American Chemical Society, vol. 107, no. 13, pp. 3902–3909, 1985. View at Scopus
- R. Schoenleber, Y. C. Martin, M. Wilson, et al., 3D QSAR: Current State, Scope, and Limitations, vol. 3, American Chemical Society Meeting, New York, NY, USA, 1991.
- R. Schoenleber, M. R. Michaelides , Y. C. Martin, et al., “Design and synthesis of dopamine D1 selective antagonists,” in Proceeding of the American Chemical Society Meeting, NewYork, NY, USA, August 1991.
- J. H. Van Drie, D. Weininger, and Y. C. Martin, “Aladdin: an integrated tool for computer-assisted molecular design and pharmacophore recognition from geometric, steric, and substructure searching of three-dimensional molecular structures,” Journal of Computer-Aided Molecular Design, vol. 3, no. 3, pp. 225–251, 1989. View at Publisher · View at Google Scholar · View at Scopus
- M. P. DeNinno, R. Schoenleber, K. E. Asin, R. MacKenzie, and J. W. Kebabian, “(1R,3S)-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-3-phenyl-1H-2-benzopyran: a potent and selective D1 agonist,” Journal of Medicinal Chemistry, vol. 33, no. 11, pp. 2948–2950, 1990. View at Scopus
- J. W. Kebabian, C. Briggs, D. R. Britton et al., “A68930: a potent and specific agonist for the D-1 dopamine receptor,” American Journal of Hypertension, vol. 3, no. 6, pp. 40S–42S, 1990. View at Scopus
- M. P. DeNinno, R. Schoenleber, R. J. Perner et al., “Synthesis and dopaminergic activity of 3-substituted 1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyrans: characterization of an auxiliary binding region in the D1 receptor,” Journal of Medicinal Chemistry, vol. 34, no. 8, pp. 2561–2569, 1991. View at Scopus
- M. P. DeNinno, R. Schoenleber, R. MacKenzie et al., “A68930: a potent agonist selective for the dopamine d receptor,” European Journal of Pharmacology, vol. 199, no. 2, pp. 209–219, 1991. View at Scopus
- M. R. Michaelides, R. Schoenleber, S. Thomas et al., “Synthesis and pharmacological evaluation of 1-(aminomethyl)-3,4-dihydro-5-hydroxy-1H-2-benzopyrans as dopamine d1 selective ligands,” Journal of Medicinal Chemistry, vol. 34, no. 10, pp. 2946–2953, 1991. View at Scopus
- J. W. Kebabian, D. R. Britton, M. P. DeNinno et al., “A-77636: a potent and selective dopamine d receptor agonist with antiparkinsonian activity in marmosets,” European Journal of Pharmacology, vol. 229, no. 2-3, pp. 203–209, 1992. View at Publisher · View at Google Scholar · View at Scopus
- J. W. Kebabian, M. P. DeNinno, R. Schoenleber, R. MacKenzie, D. R. Britton, and K. E. Asin, “A68930: a potent agonist specific for the dopamine d receptor,” Neurochemistry International, vol. 20, pp. 157S–160S, 1992. View at Scopus
- D. R. Britton, J. W. Kebabian, and P. Curzon, “Rapid reversal of denervation supersensitivity of dopamine d receptors by l-dopa or a novel dopamine d receptor agonist, A68930,” European Journal of Pharmacology, vol. 200, no. 1, pp. 89–93, 1991. View at Scopus
- P. Blanchet, P. J. Bédard, D. R. Britton, and J. W. Kebabian, “Differential effect of selective D-1 and D-2 dopamine receptor agonists on levodopa-induced dyskinesia in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-exposed monkeys,” Journal of Pharmacology and Experimental Therapeutics, vol. 267, no. 1, pp. 275–279, 1993. View at Scopus
- M. R. Michaelides, Y. Hong, S. DiDomenico et al., “(5aR,11bS)-4,5,5a,6,7,11b-hexahydro-2-propyl-3-thia-5-azacyclopent-1-ena[c]-phenanthrene-9,10-diol (A-86929): a potent and selective dopamine D1 agonist that maintains behavioral efficacy following repeated administration and characterization of its diacetyl prodrug (ABT-431),” Journal of Medicinal Chemistry, vol. 38, no. 18, pp. 3445–3447, 1995. View at Publisher · View at Google Scholar · View at Scopus
- T. W. Lovenberg, W. K. Brewster, D. M. Mottola et al., “Dihydrexidine, a novel selective high potency full dopamine D-1 receptor agonist,” European Journal of Pharmacology, vol. 166, no. 1, pp. 111–113, 1989. View at Scopus
- R. K. B. Pearce, M. Jackson, D. R. Britton et al., “Actions of the D agonists A-77636 and A-86929 on locomotion and dyskinesia in MPTP-treated L-dopa-primed common marmosets,” Psychopharmacology, vol. 142, no. 1, pp. 51–60, 1999. View at Publisher · View at Google Scholar · View at Scopus
- O. Rascol, O. Blin, C. Thalamas et al., “ABT-431, a d1 receptor agonist prodrug, has efficacy in parkinson's disease,” Annals of Neurology, vol. 45, no. 6, pp. 736–741, 1999. View at Scopus
- O. Rascol, J. G. Nutt, O. Blin et al., “Induction by dopamine D receptor agonist ABT-431 of dyskinesia similar to levodopa in patients with Parkinson disease,” Archives of Neurology, vol. 58, no. 2, pp. 249–254, 2001. View at Scopus
- W. J. Giardina and M. Williams, “Adrogolide HCL (ABT-431; DAS-431), a prodrug of the dopamine D1 receptor agonist, A-86929: Preclinical pharmacology and clinical data,” CNS Drug Reviews, vol. 7, Blackwell, Oxford, UK, 2001.
- Y. Zheng, K. C. Marsh, R. J. Bertz, T. El-Shourbagy, and A. L. Adjei, “Pulmonary delivery of a dopamine D-1 agonist, ABT-431, in dogs and humans,” International Journal of Pharmaceutics, vol. 191, no. 2, pp. 131–140, 1999. View at Publisher · View at Google Scholar · View at Scopus
- D. W. Self, D. A. Karanian, and J. J. Spencer, “Effects of the novel D1 dopamine receptor agonist ABT-431 on cocaine self-administration and reinstatement,” Annals of the New York Academy of Sciences, vol. 909, pp. 133–144, 2000. View at Scopus
- M. Haney, E. D. Collins, A. S. Ward, R. W. Foltin, and M. W. Fischman, “Effect of a selective dopamine d agonist (ABT-431) on smoked cocaine self-administration in humans,” Psychopharmacology, vol. 143, no. 1, pp. 102–110, 1999. View at Publisher · View at Google Scholar · View at Scopus
- S. A. Castner, G. V. Williams, and P. S. Goldman-Rakic, “Reversal of antipsychotic-induced working memory deficits by short-term dopamine D1 receptor stimulation,” Science, vol. 287, no. 5460, pp. 2020–2022, 2000. View at Publisher · View at Google Scholar · View at Scopus
- S. A. Castner and P. S. Goldman-Rakic, “Enhancement of working memory in aged monkeys by a sensitizing regimen of dopamine d receptor stimulation,” Journal of Neuroscience, vol. 24, no. 6, pp. 1446–1450, 2004. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
- G. Wolber, A. A. Dornhofer, and T. Langer, “Efficient overlay of small organic molecules using 3D pharmacophores,” Journal of Computer-Aided Molecular Design, vol. 20, no. 12, pp. 773–788, 2006. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus