149091-92-9
Chemical Structure
Adenophostin A
- CAS No.: 149091-92-9
- Formula:C16H26N5O18P3
- Molecular Weight:669.32
IUPAC Name: 3-fluoro-5-(((3S)-2-fluoro-3-hydroxy-7-(methylsulfonyl)-1-oxo-2,3-dihydro-1H-inden-4-yl)oxy)benzonitrile
InChIKey: RENVITLQVBEFDT-MZQFDOALSA-N
SMILES: O=P(O)(O)O[C@H]1[C@H](N2C3=NC=NC(N)=C3N=C2)O[C@@H]([C@H]1O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)OP(O)(O)=O)OP(O)(O)=O)O)CO
Biological Activity: Adenophostin A is an IP3 receptor (inositol 1,4,5-trisphosphate receptors) modulator and Ca2+ releaser, with an IC50 of 1.3 nM, an EC50 of 1.4 nM, and a Ki of 0.18 nM in rats, and an IC50 of 0.95 nM in humans. Adenophostin A activates IP3 receptors, stimulates Ca2+ release from intracellular stores and microsomes, inhibits the binding of [3H]IP3 to plasma membrane receptors, and activates chloride channels. Adenophostin A resists phosphorylation and dephosphorylation by IP3 metabolic enzymes to maintain its activity, and increases cytoplasmic [Ca2+] levels via calcium mobilization from the endoplasmic reticulum of vascular smooth muscle cells. Adenophostin A is applicable to research related to hemorrhagic shock[1][2][3].
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Adenophostin A | Adenophostin A is an IP3 receptor (inositol 1,4,5-trisphosphate receptors) modulator and Ca2+ releaser, with an IC50 of 1.3 nM, an EC50 of 1.4 nM, and a Ki of 0.18 nM in rats, and an IC50 of 0.95 nM in humans. Adenophostin A activates IP3 receptors, stimulates Ca2+ release from intracellular stores and microsomes, inhibits the binding of [3H]IP3 to plasma membrane receptors, and activates chloride channels. Adenophostin A resists phosphorylation and dephosphorylation by IP3 metabolic enzymes to maintain its activity, and increases cytoplasmic [Ca2+] levels via calcium mobilization from the endoplasmic reticulum of vascular smooth muscle cells. Adenophostin A is applicable to research related to hemorrhagic shock. | |||||||||||||||||||||
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References
- [1]. Takahashi M, et al. Adenophostins, newly discovered metabolites of Penicillium brevicompactum, act as potent agonists of the inositol 1,4,5-trisphosphate receptor. J Biol Chem. 1994;269(1):369-372. [Content Brief]
- [2]. Su X, et al. Inositol Adenophostin: Convergent Synthesis of a Potent Agonist of d-myo-Inositol 1,4,5-Trisphosphate Receptors. ACS Omega. 2020;5(44):28793-28811. Published 2020 Oct 28. [Content Brief]
- [3]. Zhou R, et al. Stimulation of the adenosine A3 receptor reverses vascular hyporeactivity after hemorrhagic shock in rats. Acta Pharmacol Sin. 2010 Apr;31(4):413-20. [Content Brief]
