Verruculogen
| Code | Size | Price |
|---|
| BVT-0443-M001 | 1 mg | £130.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
AMBIENT
Storage:
Short Term Storage: +4?C. Long Term Storage: -20?C
Documents
Further Information
Alternate Names/Synonyms:
NA 209A; TR 1
Appearance:
White to off-white solid.
CAS:
12771-72-1
Class:
6.1
EClass:
32160000
Form (Short):
solid
GHS Symbol:
GHS06
Handling Advice:
Protect from light when in solution.
Hazards:
H300, H310
InChi:
InChI=1S/C27H33N3O7/c1-14(2)11-20-29-18-12-15(35-5)8-9-16(18)21-22(29)19(13-26(3,4)37-36-20)30-24(32)17-7-6-10-28(17)25(33)27(30,34)23(21)31/h8-9,11-12,17,19-20,23,31,34H,6-7,10,13H2,1-5H3/t17-,19-,20+,23-,27+/m0/s1
InChiKey:
LRXYHMMJJCTUMY-GWXUGYLUSA-N
Long Description:
Chemical. CAS: 12771-72-1. Formula: C27H33N3O7. MW: 511.6. Isolated from Aspergillus fumigatus. Fumitremorgin-type alkaloid. Tremorgenic neurotoxic mycotoxin. Selective blocker of KCa1.1 (high-conductance Ca2+-activated K+; BK; maxi-K) channels. Decreases GABA levels in CNS. Increases spontaneous glutamate and aspartate release. At toxic doses, increases the number and decreases the affinity of DHP receptors in rat cortex. Cell cycle inhibitor at the M phase. Inhibits calmodulin and PKC activity. Has apoptotic effects on human T lymphocytes. Stimulates the growth of seedling roots of buckwheat.
MDL:
MFCD00079645
Molecular Formula:
C27H33N3O7
Molecular Weight:
511.6
Package Type:
Plastic Vial
PG:
III
Precautions:
P261, P262, P280, P301, P310, P302, P350
Product Description:
Fumitremorgin-type alkaloid. Tremorgenic neurotoxic mycotoxin. Selective blocker of KCa1.1 (high-conductance Ca2+-activated K+; BK; maxi-K) channels. Decreases GABA levels in CNS. Increases spontaneous glutamate and aspartate release. At toxic doses, increases the number and decreases the affinity of DHP receptors in rat cortex. Cell cycle inhibitor at the M phase. Inhibits calmodulin and PKC activity. Has apoptotic effects on human T lymphocytes. Stimulates the growth of seedling roots of buckwheat.
Purity:
>98% (HPLC)
Signal Word:
Danger
SMILES:
O=C(N[C@H](CCCC)C(O[Na])=O)[C@@H](C1=CN(C(OC)=O)C2=C1C=CC=C2)NC([C@H](CC(C)(C)C)NC(N3[C@H](C)CCC[C@@H]3C)=O)=OO=C1N2[C@](CCC2)([H])C(N([C@@]1(O)[C@H]3O)[C@@]4([H])CC(C)(C)OO[C@@](/C=C(C)C)([H])N5C4=C3C6=C5C=C(OC)C=C6)=O
Solubility Chemicals:
Soluble in DMSO, 100% ethanol, methanol or dichloromethane.
Source / Host:
Isolated from Aspergillus fumigatus.
Transportation:
Excepted Quantity
UN Nummer:
UN 2811
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C. Store solutions at -20°C in the dark.
References
Tremorgenic toxin from Penicillium veruculosum: R.J. Cole, et al.; Appl. Microbiol. 24, 248 (1972) | The structure of verruculogen. A tremor producing epoxide from Penicillium erruculosum: J. Fayos, et al.; JACS 96, 6785 (1974) | Verruculogen: a new substance for decreasing of GABA levels in CNS: L. Hotujac, et al.; Pharmacol. 14, 297 (1976) | Actions of tremorgenic fungal toxins on neurotransmitter release: P.J. Norris, et al.; J. Neurochem. 34, 33 (1980) | Actions of a tremorgenic mycotoxin on amino acid transmitter release in vivo: D.W. Peterson, et al.; Biochem. Pharmacol. 31, 2807 (1982) | In vitro effects of tremorgenic mycotoxins: M.I. Selala, et al.; J. Nat. Prod. 54, 207 (1991) | Tremorgenic indole alkaloids potently inhibit smooth muscle high-conductance calcium-activated potassium channels: H.H. Knaus, et al.; Biochemistry 33, 5819 (1994) | Behavioral and biochemical effects of the tremorgenic mycotoxin verruculogen: L. Intorre, et al.; Environ. Toxicol. Chem. 46, 119 (1994) | Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. II. Physico-chemical properties and structures: C.B. Cui, et al.; J. Antibiot. 49, 534 (1996) | Total synthesis of fumitremorgins and verruculogens: T. Hino & M. Nakagawa; Heterocycles 46, 673 (1997) | Modulation of calmodulin and protein kinase C activities by Penicillium mycotoxins: I. Pala, et al.; Int. J. Toxicol. 18, 91 (1999) | Genotoxicity assessment of five tremorgenic mycotoxins (fumitremorgen B, paxilline, penitrem A, verruculogen and verrucosidin) produced by molds isolated from fermented meats: M. Sabater-Vilar, et al.; J. Food Protect. 66, 2123 (2003) | Influence alkaloids from the marine-derived strain of the fungus Aspergillus fumigatus Fresen. on the growth of seedling roots of buckwheat (Fagopyrum esculentum Moench): M. Anisimov, et al.; Int. J. Res. Rev. Appl. Sci. 13, 326 (2012) | Aspergillus fumigatus toxins cause cytotoxic and apoptotic effects on human T lymphocytes (Jurkat cells): H. Malekinejad, et al.; World Mycotoxin 6, 65 (2013)