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Vinpocetine Chemische Struktur

PDE inhibitor

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Vinpocetine (Ethyl apovincaminate) is a derivative of the alkaloid Vincamine that blocks voltage-gated Na+ channels. The IC50 value of Vinpocetine on direct IKK inhibition in the cell-free system is 17.17 μM. Vinpocetine is a phosphodiesterase (PDE) inhibitor and inhibits NF-κB-dependent inflammatory responses by directly targeting IκB kinase complex (IKK), and has been widely used for the treatment of cerebrovascular disorders[1][2][3].

Vinpocetine (5-50 μM; 7 hours; VSMCs, HUVECs, A549 cells and RAW264.7 cells) potently inhibits TNF-α-induced NF-κB-dependent transcriptional activity in a dose-dependent manner with an approximate IC50 value of 25 μM. Vinpocetine do not have a significant effect on cell viability[1].Vinpocetine (50 μM; 7 hours; VSMCs, HUVECs, A549 cells and RAW264.7 cells) potently inhibits TNF-α-induced up-regulation of TNF-α, IL-1β, IL-8, MCP-1, VCAM-1, ICAM-1and MIP-2 transcripts in several cell types[1].

Vinpocetine (2.5-10 mg/kg; intraperitoneal injection; C57BL/6 mice) potently inhibits TNF-α- or LPS-induced up-regulation of proinflammatory mediators, including TNF-α, IL-1β, and MIP-2, and decreases interstitial infiltration of polymorphonuclear leukocytes in a mouse model of TNF-α- or LPS-induced lung inflammation[1].

[1]. Kye-Im Jeon et al. Vinpocetine inhibits NF-κB-dependent inflammation via an IKK-dependent but PDE-independent mechanism PNAS May 25, 2010 vol. 107 no. 21 9795-9800
[2]. Patyar S, et al. Role of vinpocetine in cerebrovascular diseases. Pharmacol Rep. 2011;63(3):618-28.
[3]. Alexandre E. Medina Vinpocetine as a potent antiinflammatory agent PNAS June 1, 2010, Vol. 107, No. 22 9921-9922.

Chemische Eigenschaften

Cas No. 42971-09-5 SDF Nein
Überlieferungen Nein
Chemical Name (41S,13aS)-ethyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate
Canonical SMILES O=C(C(N1C2=C(C3=C([H])C([H])=C([H])C([H])=C13)C([H])([H])C4([H])[H])=C([H])[C@@]5(C([H])([H])C([H])([H])[H])[C@]2([H])N4C([H])([H])C([H])([H])C5([H])[H])OC([H])([H])C([H])([H])[H]
Formula C22H26N2O2 M.Wt 350.45
Löslichkeit ≥ 5.83mg/mL in DMSO Storage Store at -20°C
Allgemeine Tipps Um eine höhere Löslichkeit zu erreichen, erwärmen Sie das Röhrchen auf 37°C und schütteln Sie es eine Weile im Ultraschallbad. Die Stammlösung kann mehrere Monate unter -20°C gelagert werden.
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