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Cyclopiazonic acid - CAS 18172-33-3 Catalog number: BADC-00156
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It is produced by the strain of Various penicillium. It's a mycotoxin and it's neurotoxic. Its toxicity is linked to its ability to specifically and reversibly inhibit sarco-endoplasmic reticulum Ca2+-ATPases.
Category
ADCs Cytotoxin
Product Name
Cyclopiazonic acid
CAS
18172-33-3
Catalog Number
BADC-00156
Molecular Formula
C20H20N2O3
Molecular Weight
336.39
Ordering Information
| Catalog Number | Size | Price | Quantity |
|---|---|---|---|
| BADC-00156 | -- | $-- |
Description
It is produced by the strain of Various penicillium. It's a mycotoxin and it's neurotoxic. Its toxicity is linked to its ability to specifically and reversibly inhibit sarco-endoplasmic reticulum Ca2+-ATPases.
Synonyms
(6aR,11aS,11bR)-10-Acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
IUPAC Name
(2R,3S,9R)-5-acetyl-6-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.02,9.03,7.015,18]octadeca-1(17),5,11(18),12,14-pentaen-4-one
Canonical SMILES
CC(=O)C1=C(N2C(C1=O)C3C(C2(C)C)CC4=C5C3=CNC5=CC=C4)O
InChI
InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,25H,7H2,1-3H3/t12-,16+,17+/m1/s1
InChIKey
RLOAZVAJNNPPDI-DQYPLSBCSA-N
Density
1.42 g/cm3
Solubility
Soluble in chloroform, DMSO
Melting Point
245-246 °C
In Vitro
The inhibitory effect of cyclopiazonic acid (CPA) was concentration-dependent with an IC50 value of 16.3 μM and a Hill coefficient of 0.98. The effect of CPA on If current was also time-dependent, and the If current amplitude was partially restored after washout. Furthermore, the steady-state activation curve of the If current was shifted to a negative potential, indicating that channel activation slowed down. Finally, the protein expression of HCN4 in HEK293 cells was markedly downregulated by CPA.
In Vivo
Chickens dosed (per os) with cyclopiazonic acid (CPA) at 0.5, 5.0, and 10 mg/kg body weight showed significant (P less than or equal to 0.05) increases in brain dopamine and serotonin concentrations 96 hr after dosing. Groups of male rats were administered 0, 0.1 or 4.0 mg CPA/kg body weight/day intragastrically (three groups per dose level) for three consecutive days and 30 min after each of these CPA doses the rats were dosed by gavage with 0, 0.1 or 2.0 mg AFB1/kg body weight/day. Six of the 12 rats given each of these nine treatments were killed on day 4 after the initial dosing, and the rest were allowed a recovery period of 4 days prior to being killed. Weight loss in the three groups receiving 2.0 mg AFB1/kg/day occurred within 24 hr of the first doses. Feed consumption by these rats was about 60% of that in the other groups. By the end of the recovery period, rats in these three groups had lost an average of 31-38 g. Feed consumption throughout the recovery period by rats in the 2.0-mg AFB1 groups was about 50% of the control value, except in the group that also received the high dose of CPA, in which it was 75%. Gross pathological findings were primarily limited to rats in the high AFB1 group, and included icterus, shrunken liver and lesions in the kidney at the cortico-medullary junction.
Application
ADCs Cytotoxin
Source
Penicillium griseofulvum
Appearance
White Solid
Purity
98% (HPLC)
Shipping
Room temperature
Storage
-20 °C
Boiling Point
598.6 °C at 760 mmHg
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