Synthesis of eudistomin D analogues and its effects on adenosine receptors.

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Ishiyama H, Ohshita K, Abe T, Nakata H, Kobayashi J

Synthesis of eudistomin D analogues and its effects on adenosine receptors.

Bioorg Med Chem. 2008 Apr 1;16(7):3825-30. doi: 10.1016/j.bmc.2008.01.041. Epub 2008 Jan 30.

PubMed ID

18262425 [ View in PubMed

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Abstract

Six analogues (1-6) of eudistomin D, a beta-carboline alkaloid from a marine tunicate Eudistoma olivaceum, were synthesized, and their affinity and selectivity for adenosine receptors A(1), A(2A), and A(3) were examined. All the synthetic compounds 1-6 did not show affinity to the adenosine A(1) receptor. Delta-carboline 3 exhibited the most potent affinity to the adenosine receptor A(3) among compounds 1-6. Delta-carbolines 3 and 4 showed better affinity than the corresponding beta-carbolines 1 and 2, respectively, while N-methylation (2, 4, and 6, respectively) of the pyrrole ring in 1, 3, and 5 resulted in the reduced affinity to the adenosine A(3) receptor. On the other hand, an eudistomin D derivative, BED, exhibited modest affinity to all the receptors A(1), A(2A), and A(3) but no selectivity.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Caffeine	Adenosine receptor A1	Ki (nM)	49000	N/A	N/A	Details
Caffeine	Adenosine receptor A2a	Ki (nM)	18100	N/A	N/A	Details