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 K_i 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].

Adenophostin A exhibits properties including high affinity, potent agonistic activity, and metabolic stability^[1]:
(1) Adenophostin A has a stronger IP₃R binding capacity than IP₃.
(2) 10 nM Adenophostin A potently activates IP₃ receptors in rat cerebellar microsomes and induces Ca²⁺ release, and this activity is blocked by the IP₃ receptor antagonist Heparin (HY-17567); it also acts as an IP₃ receptor agonist and induces Ca²⁺ release in permeabilized NG108-15 cells, with a potency approximately 45-fold higher than that of IP₃.
(3) 2 μM Adenophostin A (incubated for 30 min) is completely resistant to the metabolic effects of IP₃ 5-phosphatase and IP₃ 3-kinase.
Adenophostin A is a full agonist of IP₃R1 in permeabilized HEK-IP3R1 cells, and stimulates the release of approximately 70% of the intracellular Ca²⁺ pool^[2].
Adenophostin A (10 μM; 5 min) induces IP₃R-mediated Ca²⁺ release in hypoxic rat abdominal aortic vascular smooth muscle cells (VSMCs), whereas no significant changes are observed after stimulating A3AR with 4 μM IB-MECA^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

669.32

C₁₆H₂₆N₅O₁₈P₃

149091-92-9

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

Room temperature in continental US; may vary elsewhere.

Please store the product under the recommended conditions in the Certificate of Analysis.

• [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]