Microcystin-LR

Names

[ Name ]:
Microcystin-LR

[Synonym ]:
akerstox
TOXIN,BLUE-GREENALGA
EINECS 200-659-6
Microcystin-LR
microcystin-lr solution
1,4,7,10,14,17,21-Heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid, 15-[3-[(aminoiminomethyl)amino]propyl]-3,6,9,13,16,20-hexahydroxy-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenyl-1,3-heptadien-1-yl]-1,5,12,19-tetramethyl-2-methylene-8-(2-methylpropyl)-25-oxo-, (3E,5R,6E,8S,9E,11R,12S,13E,15S,16E,18S,19S,20E,22R)-
toxin-lr
microcystin LR
MFCD00131607
1,4,7,10,14,17,21-Heptaazacyclopentacosane-11,22-dicarboxylic acid, 15-[3-[(aminoiminomethyl)amino]propyl]-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenyl-1,3-heptadien-1-yl]-1,5,12,19-tetramethyl-2-methylene-8-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-, (5R,8S,11R,12S,15S,18S,19S,22R)-
5-L-Arginine-cyanoginosin
(3E,5R,6E,8S,9E,11R,12S,13E,15S,16E,18S,19S,20E,22R)-15-(3-Carbamimidamidopropyl)-3,6,9,13,16,20-hexahydroxy-8-isobutyl-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenyl-1,3-heptadien-1-yl]-1,5,12,19-tetramethyl-2-methylene-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid
5-L-Arginine-microcystin LA
microcystin-a
MCYST-LR
(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-Carbamimidamidopropyl)-8-isobutyl-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenyl-1,3-heptadien-1-yl]-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid
CYANOGINOSIN-LR

Biological Activity

[Description]:

Microcystin-LR is a potent inhibitor of type 1 and type 2A protein phosphatases (PP1 and PP2A), with IC50s of 1.7 nM and 0.04 nM, respectively. Sequence: Ala-D-Ala-Leu-D-{Bas}-Arg-{Oaa}-D-{Ggu}.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphatase

Research Areas >> Inflammation/Immunology

Natural Products >> Others

Peptides

[Target]

IC50: 1.7 nM (PP1), 0.04 nM (PP2A)[1].

[In Vitro]

Microcystins are toxic molecules produced by cyanobacterial blooms due to water eutrophication[2]. Microcystin-LR proves to be a potent inhibitor of type 1 (IC50=1.7 nM) and type 2A (IC50= 0.04 nM) protein phosphatases. Microcystin-LR inhibits the activity of both type 1 and type 2A phosphatases >10-fold more potently than okadaic acid under the same conditions. Type 2A protein phosphatases in dilute mammalian cell extracts are found to be completely inhibited by 0.5 nM microcystin-LR while type 1 protein phosphatases are only slightly affected at this concentration[1].

[References]

[1]. Honkanen RE, et al. Characterization of microcystin-LR, a potent inhibitor of type 1 and type 2A protein phosphatases. J Biol Chem. 1990 Nov 15;265(32):19401-4.

[2]. Lone Y, et al. Microcystin-LR Induced Immunotoxicity in Mammals. J Toxicol. 2016:8048125.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Molecular Formula ]:
C₄₉H₇₄N₁₀O₁₂

[ Molecular Weight ]:
995.172

[ Flash Point ]:
11 °C

[ Exact Mass ]:
994.548767

[ PSA ]:
340.64000

[ LogP ]:
-1.54

[ Appearance of Characters ]:
solid film

[ Index of Refraction ]:
1.598

[ Water Solubility ]:
ethanol: 1 mg/mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GT2810000

CHEMICAL NAME :: Cyanoginosin LA, 5-L-arginine-

CAS REGISTRY NUMBER :: 101043-37-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C49-H74-N10-O12

MOLECULAR WEIGHT :: 995.33

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 50 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TOXIA6 Toxicon. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 OBW, UK) V.1- 1962- Volume(issue)/page/year: 26,603,1988

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 50 ug/kg

TOXIC EFFECTS :: Cardiac - other changes Liver - hepatitis (hepatocellular necrosis), zonal Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

REFERENCE :: TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 8,221,1988

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 18 mg/m3/10M

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TOXIA6 Toxicon. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 OBW, UK) V.1- 1962- Volume(issue)/page/year: 28,605,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 32500 ng/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Kidney, Ureter, Bladder - other changes Skin and Appendages - hair

REFERENCE :: JEPOEC Journal of Environmental Pathology, Toxicology and Oncology. (Chem-Orbital, POB 134, Park Forest, IL 60466) V.5(4)- 1984- Volume(issue)/page/year: 9(3),221,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 60 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - changes in motor activity (specific assay) Skin and Appendages - hair

REFERENCE :: SCIEAS Science. (American Assoc. for the Advancement of Science, 1333 H St., NW, Washington, DC 20005) V.1- 1895- Volume(issue)/page/year: 220,1383,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5200 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CBINA8 Chemico-Biological Interactions. (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1969- Volume(issue)/page/year: 63,215,1987 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2205 ug/kg/6W-I

TOXIC EFFECTS :: Liver - other changes Liver - changes in liver weight Related to Chronic Data - death

REFERENCE :: AJBSAM Australian Journal of Biological Sciences. (Commonwealth Scientific and Industrial Research Organization, 314 Albert St., E. Melbourne, Vic. 3002, Australia) V.6- 1953- Volume(issue)/page/year: 31,209,1978

Safety Information

[ Symbol ]:

GHS02, GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H301-H311-H331-H370

[ Precautionary Statements ]:
P210-P260-P280-P301 + P310-P311

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US)

[ Hazard Codes ]:
T+

[ Risk Phrases ]:
26/27/28-36/37/38-43

[ Safety Phrases ]:
S26;S45;S36/S37/S39

[ RIDADR ]:
UN 2811 6.1/PG 1

[ WGK Germany ]:
3

[ RTECS ]:
GT2810000

[ Hazard Class ]:
6.1

Synthetic Route

Click to get detail synthetic route

Articles

Growth inhibition and microcystin degradation effects of Acinetobacter guillouiae A2 on Microcystis aeruginosa.

Res. Microbiol. 166(2) , 93-101, (2015)

Strain A2 with algicidal activity against Microcystis aeruginosa was isolated and identified with the genus Acinetobacter on the basis of phenotypic tests and 16S rRNA gene analysis. It was identified...

Protein kinase C and P2Y12 take center stage in thrombin-mediated activation of mammalian target of rapamycin complex 1 in human platelets.

J. Thromb. Haemost. 12(5) , 748-60, (2014)

Rapamycin, an inhibitor of mammalian target of rapamycin complex-1 (mTORC1), reduces platelet spreading, thrombus stability, and clot retraction. Despite an important role of mTORC1 in platelet functi...

Sensitive detection of microcystin-LR by using a label-free electrochemical immunosensor based on Au nanoparticles/silicon template/methylene blue nanocomposite.

J. Nanosci. Nanotechnol. 13(12) , 8245-52, (2013)

A label-free electrochemical immunosensor, based on a gold nanoparticles (Au NPs)/silicon template/methylene blue (MB)/chitosan (CHIT) nanocomposite-modified electrode, was fabricated for the ultrasen...