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N5148

Sigma-Aldrich

Nodularin

cyanotoxin

Synonym(s):

1,4,8,11,15-Pentaazacyclononadecane, cyclic peptide

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About This Item

Empirical Formula (Hill Notation):
C41H60N8O10
CAS Number:
118399-22-7
Molecular Weight:
824.96
MDL number:
MFCD16659855
UNSPSC Code:
12352202
PubChem Substance ID:
329818653
NACRES:
NA.77

biological source

microbial

Quality Level

200

assay

≥94% (TLC)

form

film or powder

solubility

methanol: 2 mg/mL (Further dilute to 10% (v/v) methanol. Store solutions at −20°C for up to six months.)

storage temp.

2-8°C

SMILES string

CO[C@@H](Cc1ccccc1)[C@@H](C)\C=C(C)\C=C\[C@@H]2NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](C)[C@@H](NC(=O)\C(=C\C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]2C)C(O)=O)C(O)=O

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,12,15,18-20,22H2,1-7H3,(H,45,53)(H,46,52)(H,47,51)(H,48,54)(H,55,56)(H,57,58)(H4,42,43,44)/b17-16+,23-21+,31-8-/t24-,25-,26-,28-,29-,30+,32-,34+/m0/s1

InChI key

IXBQSRWSVIBXNC-HSKGSTCASA-N

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General description

Nodularin is a cyclic pentapeptide toxin produced by the cyanobacteria Nodularia spumigena.

Application

Nodularin has been used to induce oxidative stress and analyse its dynamics in flounder liver. It has also been used as standard for identification and quantification by high performance liquid chromatography (HPLC).

Biochem/physiol Actions

Potent inhibitor of protein phosphatases types 1 and 2A. Tumor promoter in experimental animal model.; at higher doses, causes massive liver hemorrhage. Tumor-promoting effect is due to increasing oxidative stress, as evidenced by reduced levels of glutathione and appearance of oxidative damage in DNA bases.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Imed Maatouk et al.
Mutation research, 564(1), 9-20 (2004-10-12)
Microcystin-LR (MCYST-LR) and nodularin (NOD) produced by cyanobacteria are potent and specific hepatotoxins. The induction of free-radical formation, reduction of glutathione levels and induction of DNA damage are three major events found in rat hepatocytes treated with these hepatotoxins. However
Production of the cyanotoxin nodularin?a multifactorial approach
Pattanaik B, et al.
Harmful Algae, 10(1), 30-38 (2010)
Detection of nodularin in European flounder (Platichthys flesus) in the west coast of Sweden: Evidence of nodularin mediated oxidative stress
Persson KJ, et al.
Harmful Algae, 8(6), 832-838 (2009)
E Sueoka et al.
Journal of cancer research and clinical oncology, 123(8), 413-419 (1997-01-01)
Nodularin is a new liver carcinogen possessing a potent tumor-promoting activity in rat liver, mediated through inhibition of protein phosphatases 1 and 2A, and a weak initiating activity. Since we previously reported evidence that nodularin up-regulated expression of the tumor
M Namikoshi et al.
Chemical research in toxicology, 6(2), 151-158 (1993-03-01)
Dihydro derivatives of nodularin (1) and microcystin-LR (4), potent cyclic peptide hepatotoxins isolated from Nodularia spumigena and Microcystis aeruginosa, respectively, were prepared by sodium borohydride reduction of the dehydroamino acid residues. The two stereoisomers of both dihydronodularin (2 and 3)
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