A cyanotoxin
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Cylindrospermopsin

Item No. 43408

Technical Information
Formal Name
6-[(R)-hydroxy[(2aS,3R,4S,5aS,7R)-2,2a,3,4,5,5a,6,7-octahydro-3-methyl-4-(sulfooxy)-1H-1,8,8b-triazaacenaphthylen-7-yl]methyl]-2,4(1H,3H)-pyrimidinedione
CAS Number
143545-90-8
Molecular Formula
C15H21N5O7S
Formula Weight
Purity
≥98%
Formulation
A solid
Methanol: Soluble
SMILES
C[C@@H]1[C@]2([H])N3[C@@](C[C@@H]1OS(=O)(O)=O)([H])C[C@](N=C3NC2)([H])[C@H](C(NC(N4)=O)=CC4=O)O
InChi Code
InChI=1S/C15H21N5O7S/c1-6-10-5-16-14-17-8(13(22)9-4-12(21)19-15(23)18-9)2-7(20(10)14)3-11(6)27-28(24,25)26/h4,6-8,10-11,13,22H,2-3,5H2,1H3,(H,16,17)(H,24,25,26)(H2,18,19,21,23)/t6-,7+,8-,10-,11+,13-/m1/s1
InChi Key
LHJPHMKIGRLKDR-VDPNAHCISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Cylindrospermopsin is a cyanotoxin that has been found in C. raciborskii.1,2,3 It inhibits the activity of the UMP synthase complex in mouse liver homogenates with a Ki value of 10 µM.2 Cylindrospermopsin inhibits protein synthesis and decreases glutathione (GSH) levels in primary rat hepatocytes (IC50s = 1.28 and 2.38 µM, respectively) and induces DNA double-strand breaks in, and inhibits the proliferation of, HepG2 cells when used at a concentration of 0.5 µg/ml.1,3 In vivo, cylindrospermopsin increases liver and testes weight, decreases red blood cell and plasma cholesterol levels, and decreases liver cholesterol levels when administered via the drinking water at a concentration of 0.6 mg/L.2 It has been found in wastewater influent and freshwater fish.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Runnegar, M.T., Xie, C., Snider, B.B., et alIn vitro hepatotoxicity of the cyanobacterial alkaloid cylindrospermopsin and related synthetic analogues. Toxicol. Sci. 67(1), 81-87 (2002).

    2. Reisner, M., Carmeli, S., Werman, M., et alThe cyanobacterial toxin cylindrospermopsin inhibits pyrimidine nucleotide synthesis and alters cholesterol distribution in mice. Toxicol. Sci. 82(2), 620-627 (2004).

    3. Straser, A., Filipic, M., Novak, M., et alDouble strand breaks and cell-cycle arrest induced by the cyanobacterial toxin cylindrospermopsin in HepG2 cells. Mar. Drugs 11(8), 3077-3090 (2013).

    4. Hoeger, S.J., Shaw, G., Hitzfeld, B.C., et alOccurrence and elimination of cyanobacterial toxins in two Asutralian drinking water treatment plants. Toxicon 43, 639-649 (2004).

    5. Skafi, M., Vo Duy, S., Munoz, G., et alOccurrence of microcystins, anabaenopeptins and other cyanotoxins in fish from a freshwater wildlife reserve impacted by harmful cyanobacterial blooms. Toxicon 194, 44-52 (2021).