Cylindrospermopsin CAS: 143545-90-8
MF: C15H21N5O7S
MW: 415.4
A cyanotoxin inhibitor of protein synthesis.

Cylindrospermopsin (CAS 143545-90-8)

Cylindrospermopsin | CAS 143545-90-8 is rated 5.0 out of 5 by 1.
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Alternate Names: (2aS,3R,4S,5aS,7R)-7-[(S)-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)(hydroxy)methyl]-3-methyl-2a,3,4,5,5a,6,7,8-octahydro-2H-1,8,8b-triazaacenaphthylen-4-yl hydrogen sulfate
Application: Cylindrospermopsin is a cyanotoxin inhibitor of protein synthesis
CAS Number: 143545-90-8
Purity: ≥95%
Molecular Weight: 415.4
Molecular Formula: C15H21N5O7S
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Cylindrospermopsin is a cyanotoxin alkaloid natural product isolated from Cylindrospermopsis raciborskii blooms. Cylindrospermopsin is an inhibitor of protein synthesis, shown to block the in vitro activity of uridine monophosphate synthase complex. The acute toxicity of Cylindrospermopsin is described to be mediated by CYP (cytochrome p450)-generated metabolites, as inhibitors of CYP (cytochrome p450) completely blocked Cylindrospermopsin toxicity. Decreased activity in reduced glutathione (GSH) synthesis correlated with Cylindrospermopsin exposure may further support the damage caused by metabolites through diminished cellular scavenging of reactive oxygen species. Blockade of CYP (cytochrome p450) by inhibitors also protected cells from Cylindrospermopsin-mediated decreases in GSH levels, indicating that CYP (cytochrome p450)-generated metabolites may also mediate the reduction of GSH synthesis and fall in cellular levels of GSH.


References

1. Hawkins, P.R., et al. 1985. Appl. Environ. Microbiol. 50: 1292-1295. PMID: 3937492
2. Terao, K., et al. 1994. Toxicon. 32: 833-843. PMID: 7940590
3. Runnegar, M.T., et al. 1995. Biochem. Pharmacol. 49: 219-225. PMID: 7840799
4. Hawkins, P.R., et al. 1997. Toxicon. 35: 341-346. PMID: 9080590
5. Shaw, G.R., et al. 2000. Ther Drug Monit. 22: 89-92. PMID: 10688267
6. Falconer, I.R., et al. 2001. Environ. Toxicol. 16: 192-195. PMID: 11339720
7. Griffiths, D.J., 2003. Environ. Toxicol. 18: 78-93. PMID: 12635096
8. Froscio, S.M., et al. 2003. Environ. Toxicol. 18: 243-251. PMID: 12900943
9. Reisner, M., et al. 2004. Toxicol. Sci. 82: 620-627. PMID: 15342955
10. Humpage, A.R., et al. 2005. J. Toxicol. Environ. Health Part A. 68: 739-753. PMID: 16020200

Physical State :
Solid
Derived From :
Isolated from Cylindrospermopsis raciborskii.
Solubility :
Soluble in water, methanol, and DMSO.
Storage :
Store at -20° C
Density :
~2.0 g/cm3 (Predicted) (tautomer)
Refractive Index :
n20D 1.86 (Predicted)
pK Values :
pKa: -3.79 (Predicted), pKb: 15 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
RTECS :
UV9104310
PubChem CID :
MDL Number :
MFCD01939922
SMILES :

Download SDS (MSDS)

Certificate of Analysis

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Rated 5 out of 5 by from Reisner et al Reisner et al. (PubMed ID 15342955) found that the hepatotoxin, cylindrospermopsin, blocked uridine monophosphate synthase activity in mice cell free liver extract. -SCBT Publication Review
Date published: 2015-07-16
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