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Verruculogen

(Synonyms: 疣孢青霉原) 目录号 : GC17001

A tremorgenic mycotoxin

Verruculogen Chemical Structure

Cas No.:12771-72-1

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产品描述

Verruculogen is a Maxi-K potassium channels inhibitor.

Maxi-K, a potassium channel characterized by their large conductance for potassium ions through cell membranes, is activated by changes in membrane electrical potential and/or by increases in concentration of intracellular calcium ion. Maxi-K channels are critical for the regulation of several key physiological processes, such as smooth muscle tone and neuronal excitability.

In vitro: In a previous study, it was found that aflatrem, paspalitrem A, paspalitrem C, penitrem A, and paspalinine could inhibit the binding of [125I]charybdotoxin to maxi-K channels in bovine aortic smooth muscle sarcolemmal membranes. Whereas, verruculogen enhanced toxin binding. Despite their different effects on binding of [125I]charybdotoxin to maxi-K channels, all tested compounds including verruculogen were able to potently inhibit maxi-K channels in electrophysiological experiments, and other types of voltage-dependent or Ca(2+)-activated K+ channels examined were not affected [1].

In vivo: In an animal study, the mechanism of the genesis of tremor induced by verruculogen was investigated. It was found that atropine, glycine, mephenesin, and penicillamine with proven efficacy in relieving tremor of varied etiology, failed to modify verruculogen induced tremor. Oxyaminoacetic acid, which raises the CNS levels of GABA, and beta (chlorphenyl) gamma aminobutyric acid, which passes the hematoencephalic barrier, completely or partly relieved tremor and other verruculogen-induced symptoms, depending on the dose of the verruculogen administered. Picrotoxin, a GABA antagonist, increased the effect of verruculogen in the tested animals [2].

Clinical trial: So far, no clinical study has been conducted.

References:
[1] Knaus, H. G.,McManus, O.B.,Lee, S.H., et al. Tremorgenic indole alkaloids potently inhibit smooth muscle high-conductance calcium-activated potassium channels. Biochemistry 33(19), 5819-5828 (1994).
[2] Hotujac L, Stern P.  Pharmacological examination of verruculogen induced tremor. Acta Med Iugosl. 1974;28(3):223-9.

Chemical Properties

Cas No. 12771-72-1 SDF
别名 疣孢青霉原
化学名 (5R,10S,10aR)-1,10,10a,14,14aS,15bS-hexahydro-10,10a-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propen-1-yl)-5H,12H-3,4-dioxa-5a,11a,15a-triazacyclooct[lm]indeno[5,6-b]fluorene-11,15(2H,13H)-dione
Canonical SMILES O=C1N2[C@](CCC2)([H])C(N3[C@@H]4C5=C(C(C=CC(OC)=C6)=C6N5[C@@H](/C=C(C)/C)OOC(C)(C)C4)[C@H](O)[C@]31O)=O
分子式 C27H33N3O7 分子量 511.6
溶解度 Soluble in ethanol;Soluble in methanol;Soluble in DMSO;Soluble in dimethyl formamide 储存条件 Store at -20°C; protect from light
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1 mg 5 mg 10 mg
1 mM 1.9547 mL 9.7733 mL 19.5465 mL
5 mM 0.3909 mL 1.9547 mL 3.9093 mL
10 mM 0.1955 mL 0.9773 mL 1.9547 mL
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