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M4069

Sigma-Aldrich

Microcystin YR from Microcystis aeruginosa

cyanotoxin

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About This Item

Empirical Formula (Hill Notation):
C52H72N10O13
CAS Number:
Molecular Weight:
1045.19
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
Pricing and availability is not currently available.

biological source

microbial (Microcystis aerguinosa)

Quality Level

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

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

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

InChI key

OWHASZQTEFAUJC-HVUCWAFBSA-N

General description

Microcystin is a potent cyanotoxin produced by the bloom of Microcystis aeruginosa. It is harmful to aquatic animals.[1] 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.[2]

Application

Microcystin YR from Microcystis aeruginosa has been used to assess cytotoxicity in neutrophils using DNA fragmentation and cell viability assays[3] and as a reference standard in the quantification of microcystin from water samples.[4]

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.

Pictograms

Skull and crossbones

Signal Word

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 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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
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)
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)
Tomasz Jurczak et al.
Water research, 39(11), 2394-2406 (2005-06-02)
Eutrophication is a serious problem in Polish freshwaters. Mass occurrences of toxic cyanobacteria in reservoirs cause problems in the production of safe drinking water and the diversity of produced toxins complicates monitoring of freshwaters. The aim of this study was

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