ChemicalBook > CAS DataBase List > VERRUCULOGEN

VERRUCULOGEN

Product Name
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
Formula Weight
511.57
MOL File
12771-72-1.mol
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VERRUCULOGEN Property

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
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

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N-Bromosuccinimide Price

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

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]

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.

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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12771-72-1, VERRUCULOGENRelated Search:

GLYCINE ANHYDRIDE N-PHENYL-3-PIPERIDINAMINE 6-METHOXY-2,3-DIHYDRO-1H-INDOLE 2-Ethylpiperazine 2-PIPERIDYLMETHYLAMINE tert-Amyl hydroperoxide 4-Methyl-1-piperazineethanamine 3-AMINOPIPERIDINE 2-Aminoethyldiisopropylamine N,N-DI-N-BUTYLACETAMIDE 3-Ethylamino-4-methylphenol ACETIC ACID-DIISOPROPYLAMIDE (S)-(+)-1-METHYL-3-PHENYLPROPYLAMINE 2,5-Dimethylpiperazine VERRUCULOGEN CYCLO(-ALA-ALA) Propanamide, 2-hydroxy-N,N-dimethyl- (9CI) N-(1-METHYL-3-PHENYLPROPYL)-N-VALERAMIDE

  • 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)-
  • Verruculogen in Methanol
  • 12771-72-1
  • C27H35N3O7
  • C27H33N3O7
  • antibiotic