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VERRUCULOGEN

CAS No.
12771-72-1
Chemical Name:
VERRUCULOGEN
Synonyms
tr1;T1R1;TRXR1;GPR70;TAS1R1;NA 209A;GRIM-12;MGC9145;TR-1TOXIN;VERRUCOLOGEN
CBNumber:
CB0294003
Molecular Formula:
C27H33N3O7
Molecular Weight:
511.57
MDL Number:
MFCD00079645
MOL File:
12771-72-1.mol
MSDS File:
SDS
Last updated:2023-06-30 15:45:59

VERRUCULOGEN Properties

Boiling point 738.4±60.0 °C(Predicted)
Density 1.49±0.1 g/cm3(Predicted)
Flash point 2℃
storage temp. 2-8°C
solubility Soluble in ethanol;Soluble in methanol;Soluble in DMSO;Soluble in dimethyl formamide
form buffered aqueous solution
pka 10?+-.0.70(Predicted)
color White to off-white
FDA UNII S1P1U6VVZ8

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS02,GHS07
Signal word  Danger
Hazard statements  H225-H302+H312+H332-H319
Precautionary statements  P210-P261-P280-P305+P351+P338-P370+P378-P403+P235
Hazard Codes  T,Xn,F
Risk Statements  23/24/25-36-20/21/22-11
Safety Statements  36/37/39-45-36/37-26-16
RIDADR  UN 2811 6.1/PG 2
WGK Germany  3
RTECS  JH4920000
HS Code  38220090
NFPA 704
0
4 0

VERRUCULOGEN price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SAB1304378 ANTI-TAS1R1 (CENTER) antibody produced in rabbit IgG fraction of antiserum, buffered aqueous solution 12771-72-1 400μL $461 2023-01-07 Buy
Cayman Chemical 11351 Verruculogen ≥95% 12771-72-1 1mg $100 2024-03-01 Buy
Cayman Chemical 11351 Verruculogen ≥95% 12771-72-1 5mg $300 2024-03-01 Buy
Usbiological V2121-71 Verruculogen 12771-72-1 1mg $368 2021-12-16 Buy
Usbiological 226788 Verruculogen 12771-72-1 1mg $389 2021-12-16 Buy
Product number Packaging Price Buy
SAB1304378 400μL $461 Buy
11351 1mg $100 Buy
11351 5mg $300 Buy
V2121-71 1mg $368 Buy
226788 1mg $389 Buy

VERRUCULOGEN Chemical Properties,Uses,Production

Uses

Verruculogen is a tremorgenic mycotoxin, first isolated from Penicillium verruculosum in 1972. The structure was resolved as an indole alkaloid in 1974. Verruculogen is produced by several species of Penicillium and Aspergillus and its presence is a useful taxonomic phenotypic marker. The tremorgenic action of verruculogen is associated with increases in spontaneous glutamate and aspartate release, decreases in GABA levels and, at toxic doses, an increase in the number and decrease in the affinity of DHP receptors in rat cortex. In in vitro guinea pig ileum preparations, verruculogen causes an increase in contractile responses due to electrical field stimulation, attributed to enhancement of acetylcholine from presynaptic nerve terminals. Verruculogen also inhibits Ca2+-activated K+ channels, and is a cell cycle inhibitor blocking division at the M phase.

Uses

Suggested starting dilutions are as follows: ICC/IF: 1:100-1:1000, IHC-P: 1:100-1:1000, WB: 1:500-1:3000. Not yet tested in other applications. Optimal working dilutions should be determined experimentally by the end user.

Uses

Verruculogen is a tremorgenic mycotoxin isolated from species of Penicillium, Aspergillus, and other fungi. It selectively inhibits the activation of Maxi-K potassium channels by charybdotoxin with a K1/2 value of 170 nM. Verruculogen also promotes the release of excitatory neurotransmitters when injected directly into the brain of rats and, at high doses, arrests mouse mammary carcinoma cells in M phase of the cell cycle (MIC = 12.2 μM).[Cayman Chemical]

Definition

ChEBI: An organic heterohexacyclic compound that is a mycotoxic indole alkaloid isolated from Penicillium and Aspergillus species.

Biological Activity

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.

Biochem/physiol Actions

The protein encoded by this gene is a G protein-coupled receptor and is a component of the heterodimeric amino acid taste receptor T1R1+3. The T1R1+3 receptor responds to L-amino acids but not to D-enantiomers or other compounds. Most amino acids that are perceived as sweet activate T1R1+3, and this activation is strictly dependent on an intact T1R1+3 heterodimer. Multiple transcript variants encoding several different isoforms have been found for this gene. [provided by RefSeq]

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].

storage

+4°C

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.

VERRUCULOGEN Preparation Products And Raw materials

Raw materials

Preparation Products

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VERRUCULOGEN VERRUCULOGEN, PENICILLIUM VERRUCULOSUM 3h)-dione,1,10,10a,14,14a,15b-hexahydro-10,10a-dihydroxy-7-methoxy-2,2-dimeth 5h,12h-3,4-dioxa-5a,11a,15a-triazacyclooct(lm)indeno(5,6-b)fluorene-11,15(2h,1 tr1 verruculogentr1 yl-5-(2-methyl-1-propenyl)-,(5r-(5-alpha,10-alpha,10a-alpha,14a-alpha-15b-alp verruculogen from penicillium*verruculosum VERRUCULOGEN FROM PENICILLIUM VERRUCULOS VERRUCOLOGEN TR-1TOXIN (5R)-1,10,10a,14,14aα,15bα-Hexahydro-10α,10aα-dihydroxy-7-methoxy-2,2-dimethyl-5α-(2-methyl-1-propenyl)-12H-3,4-dioxa-5a,11a,15a-triazacyclooct[lm]indeno[5,6-b]fluorene-11,15(2H,13H)-dione (5R)-2,5,10,10a,11,12,13,14,14aα,15bα-Decahydro-10α,10aα-dihydroxy-7-methoxy-2,2-dimethyl-5α-(2-methyl-1-propenyl)-3,4-dioxa-5a,11a,15a-triaza-1H-cyclooct[lm]indeno[5,6-b]fluorene-11,15-dione (5R-(5alpha,10 alpha,10Aalpha,14aalpha,15balpha))-1,10,10A,14,14A,15B-hexahydro-10,10A-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propenyl)-5H,12H-3,4-dioxa-5A,11A,15A-triaza cyclooct (1m) indeno (5,6-B)fluorene-11,15(2H,13H)-dione 5H,12H-3,4-Dioxa-5A,11A,15A-triazacyclooct(lm)indeno(5,6-B)fluorene-11,15(2H,13H)-dione, 1,10,10A,14,14A,15B-hexahydro-10,10A-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propenyl)-, (5R,10S,10ar,14as,15bs)- 5H,12H-3,4-Dioxa-5A,11A,15A-triazacyclooct(lm)indeno(5,6-B)fluorene-11,15(2H,13H)-dione, 1,10,10A,14,14A,15B-hexahydro-10,10A-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propenyl)-,(5R-(5-alpha,10-alpha,10A-alpha,14A-alpha-15B-alpha))- Verruculogenresearch grade NA 209A Verruculogen NA 209A TR 1 toxin Verruculogen solution GRIM-12 MGC9145 TRXR1 TXNRD1 human Anti-TAS1R1 (N-terminal) antibody produced in rabbit GPR70 T1R1 TAS1R1 ANTI-TAS1R1 (CENTER) antibody produced in rabbit Taste receptor type 1 member 1 Anti-TAS1R1 (C-terminal) antibody produced in rabbit GWIWVUJHTCZBOP-FCXIIMTCSA-N 5H,12H-3,4-Dioxa-5a,11a,15a-triazacyclooct[lm]indeno[5,6-b]fluorene-11,15(2H,13H)-dione, 1,10,10a,14,14a,15b-hexahydro-10,10a-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propen-1-yl)-, (5R,10S,10aR,14aS,15bS)- 12771-72-1 C27H35N3O7 C27H33N3O7 antibiotic