The sea anemone purine, caissarone: Adenosine receptor antagonism

Roland A. Cooper, JoséCarlos De Freitas, Frank Porreca, Cynthia M. Eisenhour, Ronald Lukas, Ryan J. Huxtable

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Caissarone, a sea anemone iminopurine, produced an increase in the twitch response of the electrically stimulated guinea-pig ileum-myenteric plexus. In the same assay, caissarone reduced the inhibitory response to the endogenous neuromodulator, adenosine, the A1 adenosine receptor agonist, R-phenylisopropyladenosine (r-PIA), and the A2 agonist, 5′-(N-cyclopropyl)-carboxamidoadenosine (CPCA) in a dose-dependent manner. Schild plot analysis of antagonism by caissarone yielded slopes of near unity, indicating that caissarone acts as a simple competitive antagonist at the adenosine receptor. The dissociation constants (KB) for caissarone ranged from 0.53 mM to 0.78 mM. In functional nicotinic receptor assays in two human cell lines, caissarone failed either to potentiate or to reduce carbamylcholine-mediated 86Rb+ efflux. Thus, the enhancing activity of caissarone on the gut could not be attributed to activity at the ganglionic nicotinic receptor. Based on structure and pharmacological activity, caissarone appears to be the first marine product described as an adenosine receptor antagonist.

Original languageEnglish (US)
Pages (from-to)1025-1031
Number of pages7
JournalToxicon
Volume33
Issue number8
DOIs
StatePublished - 1995

Fingerprint

Sea Anemones
Purinergic P1 Receptors
Purinergic P1 Receptor Antagonists
Nicotinic Receptors
Assays
Phenylisopropyladenosine
Adenosine A1 Receptor Agonists
Myenteric Plexus
caissarone
purine
Carbachol
Ileum
varespladib methyl
Adenosine
Neurotransmitter Agents
Guinea Pigs
Cells
Pharmacology
Cell Line

ASJC Scopus subject areas

  • Toxicology

Cite this

Cooper, R. A., De Freitas, J., Porreca, F., Eisenhour, C. M., Lukas, R., & Huxtable, R. J. (1995). The sea anemone purine, caissarone: Adenosine receptor antagonism. Toxicon, 33(8), 1025-1031. https://doi.org/10.1016/0041-0101(95)00047-P

The sea anemone purine, caissarone : Adenosine receptor antagonism. / Cooper, Roland A.; De Freitas, JoséCarlos; Porreca, Frank; Eisenhour, Cynthia M.; Lukas, Ronald; Huxtable, Ryan J.

In: Toxicon, Vol. 33, No. 8, 1995, p. 1025-1031.

Research output: Contribution to journalArticle

Cooper, RA, De Freitas, J, Porreca, F, Eisenhour, CM, Lukas, R & Huxtable, RJ 1995, 'The sea anemone purine, caissarone: Adenosine receptor antagonism', Toxicon, vol. 33, no. 8, pp. 1025-1031. https://doi.org/10.1016/0041-0101(95)00047-P
Cooper RA, De Freitas J, Porreca F, Eisenhour CM, Lukas R, Huxtable RJ. The sea anemone purine, caissarone: Adenosine receptor antagonism. Toxicon. 1995;33(8):1025-1031. https://doi.org/10.1016/0041-0101(95)00047-P
Cooper, Roland A. ; De Freitas, JoséCarlos ; Porreca, Frank ; Eisenhour, Cynthia M. ; Lukas, Ronald ; Huxtable, Ryan J. / The sea anemone purine, caissarone : Adenosine receptor antagonism. In: Toxicon. 1995 ; Vol. 33, No. 8. pp. 1025-1031.
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