N5148

Nodularin

From microbial, ≥94% (TLC), PP2A inhibitor, film or powder

• 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

• Product Name: Nodularin, cyanotoxin
• 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.[1]

Application

Nodularin has been used to induce oxidative stress and analyse its dynamics in flounder liver.[1] It has also been used as standard for identification and quantification by high performance liquid chromatography (HPLC).[2]

Biochem/physiol Actions

Potent inhibitor of protein phosphatases types 1 and 2A. Tumor promoter in experimental animal model.[3]; 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.[4]

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H300 + H310 + H330,H315,H317,H319,H335
• pcodes: 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: 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