Citrinin
Product Code: AG-CN2-0101
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0101-M001 | 1 mg | £40.00 |
Quantity:
| AG-CN2-0101-M005 | 5 mg | £105.00 |
Quantity:
| AG-CN2-0101-M025 | 25 mg | £440.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
NSC 186; BRN 0088597; Antimycin
Appearance:
Yellow solid.
CAS:
518-75-2
Class:
6.1
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS06,GHS08
Handling Advice:
After reconstitution, prepare aliquots and store at -20°C.
Hazards:
H301, H311, H331, H351
InChi:
InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1
InChiKey:
CQIUKKVOEOPUDV-IYSWYEEDSA-N
Long Description:
Chemical. CAS: 518-75-2. Formula: C13H14O5. MW: 250.3. Isolated from Penicillium citrinum strain FKI-4836. Antibiotic. Antiprotozoal. Antimicrobial. Cytotoxic and genotoxic in various mammalian cells. Mitochondrial permeability transition pore (MPTP) activator. Apoptosis inducer. ERK and JNK signaling pathways activator. Nephrotoxic mycotoxin. Suppresses NO and iNOS expression via inhibition of the JAK/STAT-1alpha and NF-kappaB signaling pathways. Tubulin polymerization and mitotic spindle assembly inhibitor. Increases reactive oxygen species (ROS). Induces cell cycle arrest at the G0/G1 and G2/M phase.
MDL:
MFCD00006912
Molecular Formula:
C13H14O5
Molecular Weight:
250.3
Other data:
Solutions change color with changes in pH from yellow (pH 4.6) to red (pH 9.9).
Package Type:
Vial
PG:
III
Precautions:
P261, P264, P271, P280, P281, P301, P310, P302, P352, P304, P340
Product Description:
Antibiotic [1, 2]. Antiprotozoal. Antimicrobial [3, 6]. Cytotoxic and genotoxic in various mammalian cells [4]. Mitochondrial permeability transition pore (MPTP) activator [5-7]. Apoptosis inducer [7-9, 14]. ERK and JNK signaling pathways activator [10]. Nephrotoxic mycotoxin [11]. Suppresses NO and iNOS expression via inhibition of the JAK/STAT-1alpha and NF-kappaB signaling pathways [12]. Tubulin polymerization and mitotic spindle assembly inhibitor [13]. Increases reactive oxygen species (ROS) [14]. Induces cell cycle arrest at the G0/G1 and G2/M phase [13,14].
Purity:
>97% (HPLC)
Signal word:
Danger
SMILES:
C[C@H]1OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@@H]1C
Solubility Chemicals:
Soluble in methanol, ethanol, methylene chloride, pyridine or dioxane. Insoluble in water, chloroform or hexane.
Source / Host:
Isolated from Penicillium citrinum strain FKI-4836.
Transportation:
Excepted Quantity
UN Nummer:
UN 3462
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 3 years after receipt when stored at -20°C.
References
Citrinin: T.S. Gore, et al.; Nature 16, 157 (1946) | Citrinin as an Antibiotic: Y. Wang, et al.; Science 106, 291 (1947) | Antiprotozoal activity in citrinin: A.W. Hayes, et al.; Bull. Environ. Contam. Toxicol. 15, 429 (1976) | Cytotoxicity of citrinin in cultured kidney epithelial cell systems: M. Yoneyama, et al.; Ecotoxicol. Environ. Saf. 11, 100 (1986) | Citrinin-induced mitochondrial permeability transition: E.J. Da Lozzo, et al.; J. Biochem. Mol. Toxicol. 12, 291 (1998) | Antimicrobial activity of the mycotoxin citrinin obtained from the fungus penicillium citrinum: P.M. Mazumder, et al.; Anc. Sci. Life. 21, 191 (2002) | Citrinin induces apoptosis in HL-60 cells via activation of the mitochondrial pathway: F.Y. Yu, et al.; Toxicol. Lett. 161, 143 (2006) | Citrinin induces apoptosis via a mitochondria-dependent pathway and inhibition of survival signals in embryonic stem cells, and causes developmental injury in blastocysts: W.H. Chan; Biochem. J. 404, 317 (2007) | Citrinin induces apoptosis in mouse embryonic stem cells: W.H. Chan; IUBMB Life 60, 171 (2008) (Review) | Activation of ERK and JNK signaling pathways by mycotoxin citrinin in human cells: C.H. Chang, et al.; Toxicol. Appl. Pharmacol. 237, 281 (2009) | Toxicological properties of citrinin: D. Flajs & M. Peraica; Arh. Hig. Rada Toksikol. 60, 457 (2009) (Review) | The fungal metabolite, citrinin, inhibits lipopolysaccharide/interferon-gamma-induced nitric oxide production in glomerular mesangial cells: B.H. Liu, et al.; Int. Immunopharmacol. 10, 1608 (2010) | Mycotoxin citrinin induced cell cycle G2/M arrest and numerical chromosomal aberration associated with disruption of microtubule formation in human cells: C.H. Chang, et al.; Toxicol. Sci. 119, 84 (2011) | Citrinin-generated reactive oxygen species cause cell cycle arrest leading to apoptosis via the intrinsic mitochondrial pathway in mouse skin: R. Kumar, et al.; Toxicol. Sci. 122, 557 (2011)
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