MICROCYSTIN LA Chemical Properties

Boiling point:

1237.0±65.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

methanol: 2  mg/mL

form 

Whitish film adhered to inside of the vial.

pka

3.03±0.70(Predicted)

color 

Colorless to off-white

biological source

microbial (Microcystis aerguinosa)

EPA Substance Registry System

Cyclo[2,3-didehydro-N-methylalanyl-D-alanyl-L-leucyl-(3S)-3-methyl-D-.beta.-aspartyl-L-alanyl-(2S,3S,4E,6E,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoyl-D-.gamma.-glutamyl] (96180-79-9)

Safety Information

Hazard Codes 

T+

Risk Statements 

26/27/28-36/37/38-43

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2811 6.1/PG 1

WGK Germany 

3

RTECS 

GT2805000

MICROCYSTIN LA Usage And Synthesis

Description

Microcystins are hepatotoxic cyclic heptapeptide toxins produced by cyanobacteria. They are responsible for periodic poisonings of humans and livestock following consumption of freshwater in areas where the blue-green algae are endemic. The toxicity of microcystins is initiated by the inhibition of the catalytic activity of protein phosphatase (PP) 1 and PP2A. Microcystin-LA differs from the major microcystin variant LR with the substitution of alanine in place of the arginine. It inhibits both PP1C and PP2A with an IC₅₀ value of 0.3 nM.

Uses

Microcystin LA from algae has been used as a standard for liquid chromatography/mass spectrometry (LCMS) for toxin analysis.

Definition

ChEBI: Microcystin la is a peptide.

General Description

Microcystin is a small, monocyclic peptide, composed of seven amino acids connected via peptide bonds. It is a cyanotoxin with hepatotoxic and tumor promoting properties. Several algal genera like Anabaena, Aphanizomenon, Microcystis and Planktothrix produce microcystin. Microcystin has four congeners namely, -LR, -LA, -YR and -RR.

Biochem/physiol Actions

Microcystin LA inhibits protein phosphatase type 2A and protein phosphatase type 3 more potently than protein phosphatase type 1 (order of potency PP2A > PP3 > PP1). Induces neutrophil-activating chemokines and extracellular reactive oxygen species, possible mechanisms of its hepatotoxic effects.

References

[1] J B AGGEN. The design, synthesis, and biological evaluation of analogues of the serine-threonine protein phosphatase 1 and 2A selective inhibitor microcystin LA: rational modifications imparting PP1 selectivity.[J]. Bioorganic & Medicinal Chemistry, 1999, 7 3: 543-564. DOI: 10.1016/s0968-0896(98)00254-5
[2] NEIL CHERNOFF. Dose-Response Study of Microcystin Congeners MCLA, MCLR, MCLY, MCRR, and MCYR Administered Orally to Mice.[J]. ACS Applied Electronic Materials, 2021. DOI: 10.3390/toxins13020086
[3] MOURAD SKAFI . Occurrence of microcystins, anabaenopeptins and other cyanotoxins in fish from a freshwater wildlife reserve impacted by harmful cyanobacterial blooms[J]. Toxicon, 2021, 194: Pages 44-52. DOI: 10.1016/j.toxicon.2021.02.004

MICROCYSTIN LA(96180-79-9)Related Product Information

• Microcystin (N-Methyl-L)R ("MC(N-Me)LR")
• Algae bloom toxin, Biotoxin, Cyanobacterial toxin
• MICROCYSTIN YR
• Microcystin HtyR
• Algae bloom standard, Algae bloom toxin, Biotoxin, Cyanobacterial toxin
• Microcystin-WR
• microcystin LY