101043-37-2

Basic information

• Product Name: MICROCYSTIN-LR
• Synonyms: 5-l-arginine-cyanoginosinl;5-l-argininecyanoginosinla;akerstox;microcystin-a;microcystisaeruginosatoxin;toxin,bluegreenalga,microcystisaeruginosa;toxini(microcystisaeruginosa);toxin-lr
• CAS NO: 101043-37-2
• Molecular Formula: C₄₉H₇₄N₁₀O₁₂
• Molecular Weight: 995.17166
• EINECS: 200-659-6
• Product Categories: Natural Products
• Mol File: 101043-37-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: 11 °C
• Appearance: /solid film
• Density: 1.29g/cm³
• Refractive Index: 1.598
• Storage Temp.: −20°C
• Solubility: ethanol: 1 mg/mL
• PKA: 3.03±0.70(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO, methanol or ethanol may be stored at -20°C for up to 2 months.
• CAS DataBase Reference: MICROCYSTIN-LR(CAS DataBase Reference)
• NIST Chemistry Reference: MICROCYSTIN-LR(101043-37-2)
• EPA Substance Registry System: MICROCYSTIN-LR(101043-37-2)

Safety Data

• Hazard Codes: T+,T,F
• Statements: 26/27/28-36/37/38-43-39/23/24/25-23/24/25-11
• Safety Statements: 26-36/37/39-45-36/37-16-7
• RIDADR: UN 2811 6.1/PG 1
• WGK Germany: 3
• RTECS: GT2810000
• Hazardous Substances Data: 101043-37-2(Hazardous Substances Data)

Usage

Chemical Description

Microcystin-LR is a hepatotoxin produced by cyanobacteria, while the photoreaction products are the nontoxic compounds formed when Microcystin-LR is exposed to UV.

Description

Microcystins are hepatotoxic cyclic heptapeptide toxins produced by cyanobacteria. They are responsible for periodic poisonings of humans and livestock drinking fresh water where the blue-green algae are endemic. Microcystin-LR is a selective inhibitor of protein phosphatase 2A (PP2A) (IC50= 0.04 nM) and will completely inhibit this enzyme without affecting PP1 when used at a concentration of 0.5 nM. The PP1 IC50 is about 1.7 nM. Microcystins are at least 10 times more potent as serine/threonine PP inhibitors than okadaic acid, another microalgal toxin also used for this purpose.

Safety Profile

A poison by ingestion, inhalation,intraperitoneal, and intravenous route. Experimentalreproductive effects. When heated to decomposition itemits toxic vapors of NOx.

References

1) Rinehart?et al.?(1988),?Nodularin, microcystin, and the configuration of Adda; J. Am. Chem. Soc.,?110?8557 2) Honkanen?et al. (1990),?Characterization of microcystin-LR, a potent inhibitor of type 1 and type 2A protein phosphatases;?J. Biol. Chem,?265?19401 3) Runnegar?et al.?(1995),?Microcystin uptake and inhibition of protein phosphatases: effects of chemoprotectants and self-inhibition in relation to known hepatic transporters; Toxicol. Appl. Pharmacol.,?134?264

InChI:InChI=1/C49H74N10O12/c1-26(2)23-37-46(66)58-40(48(69)70)30(6)42(62)55-35(17-14-22-52-49(50)51)45(65)54-34(19-18-27(3)24-28(4)38(71-10)25-33-15-12-11-13-16-33)29(5)41(61)56-36(47(67)68)20-21-39(60)59(9)32(8)44(64)53-31(7)43(63)57-37/h11-13,15-16,18-19,24,26,28-31,34-38,40H,8,14,17,20-23,25H2,1-7,9-10H3,(H,53,64)(H,54,65)(H,55,62)(H,56,61)(H,57,63)(H,58,66)(H,67,68)(H,69,70)(H4,50,51,52)/b19-18+,27-24+/t28-,29-,30-,31+,34-,35-,36+,37+,38-,40+/m0/s1

Upstream product

• 205104-07-0 [(2S,3S,1'R,3'S,4'S,5'R,6'R,7'R)-3-amino-5-(4',6'-dimethyl-3'-methoxytricyclo[5.4.0.0^1'5']undeca-8',10'-dien-6'-yl)-2-methyl-4(E)-pentenoic acid]microcystin-LR 

Downstream Products

• 324518-25-4 C₅₁H₈₁N₁₁O₁₂S 
• 205104-07-0 [(2S,3S,1'R,3'S,4'S,5'R,6'R,7'R)-3-amino-5-(4',6'-dimethyl-3'-methoxytricyclo[5.4.0.0^1'5']undeca-8',10'-dien-6'-yl)-2-methyl-4(E)-pentenoic acid]microcystin-LR 
• 129678-94-0 [3H]-Dihydromicrocystin LR 

Related news

Recovery of reproductive function of female zebrafish from the toxic effects of MICROCYSTIN-LR (cas 101043-37-2) exposure08/18/2019

Fish has a strong resistance to microcystins (MCs), cyclic heptapeptide cyanotoxins, known as endocrine disrupting chemicals (EDCs) which are released during cyanobacterial blooms and many laboratory and field studies have found the hepatic recovery of fish from the MCs exposure. The aim of the ...detailed

Relevant articles and documents

A photodetoxification mechanism of the cyanobacterial hepatotoxin microcystin-LR by ultraviolet irradiation

When microcystin-LR was exposed to UV, three major nontoxic compounds were formed. These compounds were identified as [4(E),6(Z)-Adda5]- and [4(Z),6(E)-Adda5]microcystin-LR, which are geometrical isomers of the Adda [3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4(E),6(E)-decadienoic acid] moiety of microcystin-LR, and a novel compound, tricyclo-Adda [(2S,3S,1'R,3'S,4'S,5'R,6'R,7'R)-3-amino-5-(4',6-dimethy-3'- methoxytricyclo[5.4.0.0(1',5)]undeca-8',10'-dien-6'-yl)-2-methyl-4(E)- pentenoic acid]-containing microcystin-LR ([tricyclo-Adda5]-microcystin- LR), which was formed by [2 + 2] addition between the benzene ring and the double bond at position 6-7 of the Adda moiety of the microcystin. The geometrical isomers were formed reversibly, and their equilibrium constants were almost the same. [Tricyclo-Adda5]-microcystin-LR was also formed reversibly and was decomposed under UV light. These results suggest that the breakdown of microcystin-LR by UV irradiation proceeds via [tricyclo-Adda5]- microcystin-LR.