A cyanotoxin and an inhibitor of PP2A
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Nodularin

Item No. 10007190

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclo[3S-amino-9S-methoxy-2S,6E,8S-trimethyl-10-phenyl-4,6-decadienoyl-D-γ-glutamyl-(2Z)-2-(methylamino)-2-butenoyl-(3S)-3-methyl-D-β-aspartyl-L-arginyl]
CAS Number
118399-22-7
Synonyms
  • NODLN
Molecular Formula
C41H60N8O10
Formula Weight
825.0
Purity
≥95%
Formulation
A clear film
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/mlEthanol: 10 mg/mlMethanol:Water (1:1): 1 mg/ml
SMILES
CC(/C=C/[C@@]([H])(NC([C@@H](CCCNC(N)=N)NC([C@H](C)[C@@H](C(O)=O)NC/1=O)=O)=O)[C@@H](C)C(N[C@H](C(O)=O)CCC(N(C)C1=C/C)=O)=O)=C\[C@H]([C@@H](CC2=CC=CC=C2)OC)C
InChi Code
InChI=1S/C41H60N8O10/c1-8-31-38(54)48-34(40(57)58)26(5)36(52)46-29(15-12-20-44-41(42)43)37(53)45-28(25(4)35(51)47-30(39(55)56)18-19-33(50)49(31)6)17-16-23(2)21-24(3)32(59-7)22-27-13-10-9-11-14-27/h8-11,13-14,16-17,21,24-26,28-30,32,34H,12,15,18-20,22
InChi Key
IXBQSRWSVIBXNC-RLYCYGFOSA-N
Bureau of Industry & Security
Regulated
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 µg

    $152

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    Product Description

    Nodularin is a cyanotoxin and an inhibitor of protein phosphatase 2A (PP2A; IC50 = 0.021 nM).1,2 It is selective for PP2A over PP1 and PP2B (IC50s = 2.1 and 8,700 nM, respectively), as well as alkaline phosphatase (ALP), acid phosphatase, protein kinase A (PKA), PKC, and phosphorylase kinase at 1 µM. Nodularin (25 µg/kg) decreases serum and testis testosterone levels, increases serum cholesterol levels, and induces apoptosis in spermatogonia and the prostate in male mice when used in combination with the carcinogen diethylnitrosamine in a model of hepatocarcinogenesis.3 It induces enlargement of hepatic tubules, distortion of the hepatic tubule epithelium, and exfoliation of the intestinal epithelium, as well as increases malondialdehyde (MDA) levels and the activity of superoxide dismutase (SOD), catalase (CAT), and peroxidase in the hepatopancreas and intestine in Pacific white shrimp (L. vannamei) when used at a concentration of 1 µg/L.1 It has been found in lakes with cyanobacterial mats and in Baltic fish.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Duan, Y., Xing, Y., Huang, J., et al. Toxicological response of pacific white shrimp Litopenaeus vannamei to a hazardous cyanotoxin nodularin exposure. Environ. Pollut. 318, 120950 (2023).

    2. Honkanen, R.E., Dukelow, M., Zwiller, J., et al. Cyanobacterial nodularin is a potent inhibitor of type 1 and type 2A protein phosphatases. Mol. Pharmacol. 40(4), 577-583 (1991).

    3. Park, T.J., Song, K.Y., Sohn, S.H., et al. Marked inhibition of testosterone biosynthesis by the hepatotoxin nodularin due to apoptosis of leydig cells. Mol. Carcinog. 34(3), 151-163 (2002).

    4. Mountfort, D.O., Holland, P., and Sprosen, J. Method for detecting classes of microcystins by combination of protein phosphatase inhibition assay and ELISA: Comparison with LC-MS. Toxicon 45(2), 199-206 (2005).

    5. Sipiä, V.O., Kankaanpää, H.T., Lahti, K., et al. Detection of nodularin in flounders and cod from the Baltic Sea. Environ. Toxicol. 16(2), 121-126 (2001).