The sea anemone purine, caissarone: Adenosine receptor antagonism

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

doi:10.1016/0041-0101(95)00047-p

Cited by 26 publications

(18 citation statements)

References 16 publications

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“…Thus, the molecular target of 5 was deduced to be adenosine receptors, although the potency was much lower than that of theophylline. 10 Compound 6 exhibited similar but weaker activity compared to 5 .…”

Section: Discussionmentioning

confidence: 96%

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Novel N-Methylated 8-Oxoisoguanines from Pacific Sponges with Diverse Neuroactivities

et al. 2010

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Marine organisms have yielded a variety of metabolites with neuropharmacological applications. Here we describe the isolation and pharmacological characterization of four novel, neurologically active purines 1–4, isolated from Haplosclerida sponges collected in the Republic of Palau. The structures were determined by analyses of spectral and X-ray data. Compound 1 induced convulsions upon intracerebroventricular injection into mice, with a CD50 value of 2.4 nmol/mouse. Purines 2–4 were active in mouse bioassays at higher doses. The seizurogenic activity of 1 was correlated with inhibition of neuronal GABAergic transmission, with only a modest impact on excitatory signaling, in electrophysiological recordings from hippocampal neurons. Despite having a purine template structure, the inhibitory activity of 1 was not prevented by a nonselective adenosine receptor antagonist. Thus, 1 represents a novel substituted purine that elicits convulsions through its actions on inhibitory neurotransmission. These 8-oxoisoguanine analogs comprise a new family of compounds closely related in structure to endogenous neurosignaling molecules and commonly used CNS stimulants.

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Section: Discussionmentioning

confidence: 96%

“…The bioactivity of marine-derived purines is diverse and includes cytotoxicity, 3 antimicrobial activity, 4,5 enzyme inhibition, 6,7 antiangiogenic activity, 8 and alteration of neuronal signaling. 9,10 …”

Section: Introductionmentioning

confidence: 99%

Novel N-Methylated 8-Oxoisoguanines from Pacific Sponges with Diverse Neuroactivities

et al. 2010

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“…Structural elucidation was obtained via acrystal structure of its acyl derivative. [70] Another derivativei ncludest he benzyl substituted 8-oxoAde, which was isolated and characterized from am arine ascidian that resulted in aplidiamine. [67] Another alkylated derivative is Caissarone, which is an N3-, N6-, N9-methylated compound that was isolated and characterizedv ia X-ray crystallography.…”

Section: Naturalproduct Derivativesmentioning

confidence: 99%

8‐Oxo‐7,8‐dihydroadenine and 8‐Oxo‐7,8‐dihydroadenosine—Chemistry, Structure, and Function in RNA and Their Presence in Natural Products and Potential Drug Derivatives

Choi

Chang

Gibala

et al. 2017

Chemistry A European J

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A description and history of the role that 8-oxo-7,8-dihydroadenine (8-oxoAde) and 8-oxo-7,8-dihydroadenosine (8-oxoA) have in various fields has been compiled. This Review focusses on 1) the formation of this oxidatively generated modification in RNA, its interactions with other biopolymers, and its potential role in the development/progression of disease; 2) the independent synthesis and incorporation of this modified nucleoside into oligonucleotides of RNA to display the progress that has been made in establishing its behavior in biologically relevant systems; 3) reported synthetic routes, which date back to 1890, along with the progress that has been made in the total synthesis of the nucleobase, nucleoside, and their corresponding derivatives; and 4) the isolation, total synthesis, and biological activity of natural products containing these moieties as the backbone. The current state of research regarding this oxidatively generated lesion as well as its importance in the context of RNA, natural products, and potential as drug derivatives is illustrated using all available examples reported to date.

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“…Caissarone ( 200 ) 258 and 1,3-dimethylisoguanine ( 201 ), 259 are products of sea anemones and sponges, respectively. Caissarone-induced twitch in electrically stimulated guinea pig ileum-myenteric plexus was attributed to antagonistic actions on adenosine receptors.…”

Section: Molecules That Target Neurotransmitter Receptorsmentioning

confidence: 99%