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Merck
CN

M4069

Microcystin YR from Microcystis aeruginosa

cyanotoxin

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About This Item

Empirical Formula (Hill Notation):
C52H72N10O13
CAS Number:
101064-48-6
Molecular Weight:
1045.19
UNSPSC Code:
12352202
PubChem Substance ID:
24896901
MDL number:
MFCD00236437

Key Documents

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Product Name

Microcystin YR from Microcystis aeruginosa, cyanotoxin

InChI

1S/C52H72N10O13/c1-28(25-29(2)41(75-8)27-34-13-10-9-11-14-34)16-21-37-30(3)44(65)59-39(50(71)72)22-23-42(64)62(7)33(6)47(68)56-32(5)46(67)60-40(26-35-17-19-36(63)20-18-35)49(70)61-43(51(73)74)31(4)45(66)58-38(48(69)57-37)15-12-24-55-52(53)54/h9-11,13-14,16-21,25,29-32,37-41,43,63H,6,12,15,22-24,26-27H2,1-5,7-8H3,(H,56,68)(H,57,69)(H,58,66)(H,59,65)(H,60,67)(H,61,70)(H,71,72)(H,73,74)(H4,53,54,55)/b21-16+,28-25+/t29-,30-,31+,32+,37-,38-,39+,40-,41-,43+/m0/s1

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@H](Cc3ccc(O)cc3)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]2C)C(O)=O)C(O)=O

InChI key

OWHASZQTEFAUJC-HVUCWAFBSA-N

biological source

microbial (Microcystis aerguinosa)

assay

≥90% (HPLC)

form

powder

mol wt

~1.0 kDa

color

white

solubility

methanol: 2 mg/mL ((further dilute to 10% (v/v) methanol))
DMSO: soluble
ethanol: soluble

storage temp.

−20°C

Quality Level

200

Application

Microcystin YR from Microcystis aeruginosa has been used to assess cytotoxicity in neutrophils using DNA fragmentation and cell viability assays and as a reference standard in the quantification of microcystin from water samples.

Biochem/physiol Actions

Microcystin YR inhibits protein phosphatase type 2A and protein phosphatase type 1.
Microcystin YR inhibits protein phosphatase type 2A and protein phosphatase type 1. Toxicity to undifferentiated cells was seen by inhibition of neutral red uptake, >80% at 100 μM, after 48 h.

General description

Microcystin is a potent cyanotoxin produced by the bloom of Microcystis aeruginosa. It is harmful to aquatic animals. It is a heptapeptide and exists as multiple variant forms. pCO2 and nitrogen levels modulate the toxic variants levels. It elicits damage to the liver and other organs.

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBS2570V
SLBR1121V
SLBK9229V
SLBH8446V
SLBG7589V

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BIO-CONTROL OF MICROCYSTIS AERUGINOSA BLOOM USING VARIOUS AQUATIC ORGANISMS BY DUAL STABLE ISOTOPE (13 C AND 15 N) TRACERS
Kim MS, et al.
APPLIED ECOLOGY AND ENVIRONMENTAL RESEARCH, 16(2), 931-953 (2018)
Elevated pCO2 causes a shift towards more toxic microcystin variants in nitrogen-limited Microcystis aeruginosa
Liu J, et al.
FEMS Microbiology Ecology, 92(2) (2016)
Analysis of chemokines and reactive oxygen species formation by rat and human neutrophils induced by microcystin-LA,-YR and-LR
Kujbida P, et al.
Toxicon, 51(7), 1274-1280 (2008)
Accumulation of microcystin (LR, RR and YR) in three freshwater bivalves in Microcystis aeruginosa bloom using dual isotope tracer
Kim MS, et al.
Marine drugs, 15(7), 226-226 (2017)
Xiaofeng Wang et al.
Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering, 37(7), 1181-1207 (2004-08-27)
Three heptapeptide toxins, microcystin-RR, microcystin-RY and microcystin-LR, which can cause health problems in animals and humans were monitored in Bang Phra Reservoir, Thailand using reversed-phase high performance liquid chromatography. The concentrations of the three toxins in the reservoir varied greatly
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