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Merck
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N5148

Sigma-Aldrich

节球毒素

cyanotoxin

别名:

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

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About This Item

经验公式（希尔记法）:
C41H60N8O10
CAS号:
118399-22-7
分子量:
824.96
MDL编号:
MFCD16659855
UNSPSC代码:
12352202
PubChem化学物质编号:
329818653
NACRES:
NA.77

生物来源

microbial

质量水平

200

方案

≥94% (TLC)

表单

film or powder

溶解性

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

储存温度

2-8°C

SMILES字符串

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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一般描述

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

应用

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).

生化/生理作用

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.

象形图

Skull and crossbones
GHS06

警示用语：

Danger

危险分类

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

靶器官

Respiratory system

储存分类代码

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

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000373800
0000364280
0000358760
0000358760
0000364280

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Sigma-Aldrich

A2263

α-天麻素

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
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)
Production of the cyanotoxin nodularin?a multifactorial approach
Pattanaik B, et al.
Harmful Algae, 10(1), 30-38 (2010)
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