N5148

Nodularin

cyanotoxin

• Synonym(s): 1,4,8,11,15-Pentaazacyclononadecane, cyclic peptide
• 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

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H300 + H310 + H330 - H315 - H317 - H319 - H335
• Precautionary Statements: P260 - P262 - P280 - P302 + P352 + P310 - P304 + P340 + P310 - P305 + P351 + P338
• 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 Code: 6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable