AdipoGen Life Sciences

Citrinin

CHF 45.00
In stock
AG-CN2-0101-M0011 mgCHF 45.00
AG-CN2-0101-M0055 mgCHF 140.00
AG-CN2-0101-M02525 mgCHF 560.00
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Product Details
Synonyms NSC 186; BRN 0088597; Antimycin
Product Type Chemical
Properties
Formula

C13H14O5

MW 250.3
Merck Index 14: 2327
CAS 518-75-2
RTECS DJ2275000
Source/Host Chemicals Isolated from Penicillium citrinum strain FKI-4836.
Purity Chemicals ≥97% (HPLC)
Appearance Yellow solid.
Solubility Soluble in methanol, ethanol, methylene chloride, pyridine or dioxane. Insoluble in water, chloroform or hexane.
Other Product Data

Solutions change color with changes in pH from yellow (pH 4.6) to red (pH 9.9).

InChi Key CQIUKKVOEOPUDV-IYSWYEEDSA-N
Smiles C[C@H]1OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@@H]1C
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice After reconstitution, prepare aliquots and store at -20°C.
Use/Stability Stable for at least 3 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
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-1α and NF-κB 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].
Product References
  1. Citrinin: T.S. Gore, et al.; Nature 16, 157 (1946)
  2. Citrinin as an Antibiotic: Y. Wang, et al.; Science 106, 291 (1947)
  3. Antiprotozoal activity in citrinin: A.W. Hayes, et al.; Bull. Environ. Contam. Toxicol. 15, 429 (1976)
  4. Cytotoxicity of citrinin in cultured kidney epithelial cell systems: M. Yoneyama, et al.; Ecotoxicol. Environ. Saf. 11, 100 (1986)
  5. Citrinin-induced mitochondrial permeability transition: E.J. Da Lozzo, et al.; J. Biochem. Mol. Toxicol. 12, 291 (1998)
  6. Antimicrobial activity of the mycotoxin citrinin obtained from the fungus penicillium citrinum: P.M. Mazumder, et al.; Anc. Sci. Life. 21, 191 (2002)
  7. Citrinin induces apoptosis in HL-60 cells via activation of the mitochondrial pathway: F.Y. Yu, et al.; Toxicol. Lett. 161, 143 (2006)
  8. 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)
  9. Citrinin induces apoptosis in mouse embryonic stem cells: W.H. Chan; IUBMB Life 60, 171 (2008) (Review)
  10. Activation of ERK and JNK signaling pathways by mycotoxin citrinin in human cells: C.H. Chang, et al.; Toxicol. Appl. Pharmacol. 237, 281 (2009)
  11. Toxicological properties of citrinin: D. Flajs & M. Peraica; Arh. Hig. Rada Toksikol. 60, 457 (2009) (Review)
  12. The fungal metabolite, citrinin, inhibits lipopolysaccharide/interferon-γ-induced nitric oxide production in glomerular mesangial cells: B.H. Liu, et al.; Int. Immunopharmacol. 10, 1608 (2010)
  13. 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)
  14. 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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