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MedKoo Cat#: 592367 | Name: Microcystin-LR
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Microcystin-LR is a Cyclic heptapeptide from cyanobacterium Microcystis aeruginosa. It is an immunosensor.

Chemical Structure

Microcystin-LR
Microcystin-LR
CAS#101043-37-2

Theoretical Analysis

MedKoo Cat#: 592367

Name: Microcystin-LR

CAS#: 101043-37-2

Chemical Formula: C49H74N10O12

Exact Mass: 994.5488

Molecular Weight: 995.19

Elemental Analysis: C, 59.14; H, 7.50; N, 14.07; O, 19.29

Price and Availability

Size Price Availability Quantity
1mg USD 950.00 2 Weeks
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Synonym
Microcystin-LR; Microcystin; Microcystin-a; Microcystin-LR; Cyanoginosin-LR; Toxin T 17 (M. aeruginosa); MC-LR;
IUPAC/Chemical Name
Cyanoginosin LA, 5-L-arginine-
InChi Key
ZYZCGGRZINLQBL-GWRQVWKTSA-N
InChi Code
InChI=1S/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
SMILES Code
CO[C@H]([C@H](/C=C(/C=C/[C@@H]1NC([C@@H](NC([C@H]([C@H](C(O)=O)NC([C@@H](NC([C@H](NC(C(N(C(CC[C@H](C(O)=O)NC([C@H]1C)=O)=O)C)=C)=O)C)=O)CC(C)C)=O)C)=O)CCCNC(N)=N)=O)C)C)Cc2ccccc2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
Instruction
View handling instruction
Biological target:
Microcystin-LR is a Cyclic heptapeptide from cyanobacterium Microcystis aeruginosa.
In vitro activity:
100 nM MC-LR (microcystin-LR) promoted the proliferation, migration, invasion, and anti-apoptosis of SGC-7901 cells. Quantitative proteome and phosphoproteome analysis identified differential expression patterns and aberrant pathways of SGC-7901 cells exposed to MC-LR. The results indicated that 48,109 unique peptides from 6320 proteins and 1375 phosphoproteins with 3473 phosphorylation sites were detected after 24 h treatment of MC-LR. Reference: Environ Pollut. 2023 Jan 15;317:120744. https://pubmed.ncbi.nlm.nih.gov/36436660/
In vivo activity:
This study investigated the effects of MCLR (microcystin-leucine arginine) on the intestinal epithelial microenvironment by oral administration of MCLR. As expected, MCLR at doses of 200 and 400 μg kg-1 bw showed hepatorenal toxicity in rats but without significant gastrointestinal symptoms. MCLR exposure decreased the thickness of the colonic epithelial mucus layer, and down-regulated the expression of main mucin protein (MUC2), cytoskeletal assembly-related genes (Arpc1a, Enah) and cytoskeletal stability-related genes (Ptk2, Prkca, Actn1, Pxn, Tln1, Cttn, Vcl) in colonic tissue to varying degrees, but did not affect the expression of cell connection-related genes including Zo1, Ocln, Cldn2 and Cdh1. Reference: Food Chem Toxicol. 2023 Mar;173:113611. https://pubmed.ncbi.nlm.nih.gov/36657700/
Solvent mg/mL mM comments
Solubility
Ethanol 10.0 10.05
Methanol 10.0 10.05
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 995.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Yang P, Zhang P, Deng Y, Liao Y, Guo X, Sun M, Yin L, Liu R. Comprehensive proteomic and phosphoproteomic reveal that Microcystin-LR contributed to the malignant progression of gastric cancer by estrogenic potency. Environ Pollut. 2023 Jan 15;317:120744. doi: 10.1016/j.envpol.2022.120744. Epub 2022 Nov 24. PMID: 36436660. 2. Wang X, Zhu Y, Lu W, Guo X, Chen L, Zhang N, Chen S, Ge C, Xu S. Microcystin-LR-induced nuclear translocation of cGAS promotes mutagenesis in human hepatocytes by impeding homologous recombination repair. Toxicol Lett. 2023 Jan 15;373:94-104. doi: 10.1016/j.toxlet.2022.11.015. Epub 2022 Nov 23. PMID: 36435412. 3. Du X, Fu Y, Tian Z, Liu H, Xin H, Fu X, Wang F, Zhang H, Zeng X. Microcystin-LR accelerates follicular atresia in mice via JNK-mediated adherent junction damage of ovarian granulosa cells. Ecotoxicol Environ Saf. 2023 Mar 1;252:114592. doi: 10.1016/j.ecoenv.2023.114592. Epub 2023 Feb 1. PMID: 36731181. 4. Liu Y, Qi CL, Li DW, Li HY, Li RM, Yang WD. Microcystin-LR exposure interfered maintenance of colonic microenvironmental homeostasis in rat. Food Chem Toxicol. 2023 Mar;173:113611. doi: 10.1016/j.fct.2023.113611. Epub 2023 Jan 16. PMID: 36657700.
In vitro protocol:
1. Yang P, Zhang P, Deng Y, Liao Y, Guo X, Sun M, Yin L, Liu R. Comprehensive proteomic and phosphoproteomic reveal that Microcystin-LR contributed to the malignant progression of gastric cancer by estrogenic potency. Environ Pollut. 2023 Jan 15;317:120744. doi: 10.1016/j.envpol.2022.120744. Epub 2022 Nov 24. PMID: 36436660. 2. Wang X, Zhu Y, Lu W, Guo X, Chen L, Zhang N, Chen S, Ge C, Xu S. Microcystin-LR-induced nuclear translocation of cGAS promotes mutagenesis in human hepatocytes by impeding homologous recombination repair. Toxicol Lett. 2023 Jan 15;373:94-104. doi: 10.1016/j.toxlet.2022.11.015. Epub 2022 Nov 23. PMID: 36435412.
In vivo protocol:
1. Du X, Fu Y, Tian Z, Liu H, Xin H, Fu X, Wang F, Zhang H, Zeng X. Microcystin-LR accelerates follicular atresia in mice via JNK-mediated adherent junction damage of ovarian granulosa cells. Ecotoxicol Environ Saf. 2023 Mar 1;252:114592. doi: 10.1016/j.ecoenv.2023.114592. Epub 2023 Feb 1. PMID: 36731181. 2. Liu Y, Qi CL, Li DW, Li HY, Li RM, Yang WD. Microcystin-LR exposure interfered maintenance of colonic microenvironmental homeostasis in rat. Food Chem Toxicol. 2023 Mar;173:113611. doi: 10.1016/j.fct.2023.113611. Epub 2023 Jan 16. PMID: 36657700.
1: Wei J, Chang W, Qileng A, Liu W, Zhang Y, Rong S, Lei H, Liu Y. Dual-modal split-type immunosensor for sensitive detection of microcystin-LR: enzyme-induced photoelectrochemistry and colorimetry. Anal Chem. 2018 Jul 9. doi: 10.1021/acs.analchem.8b02546. [Epub ahead of print] PubMed PMID: 29985599. 2: Costa ML, Rodrigues JA, Azevedo J, Vasconcelos V, Eiras E, Campos MG. Hepatotoxicity induced by paclitaxel interaction with turmeric in association with a microcystin from a contaminated dietary supplement. Toxicon. 2018 May 29;150:207-211. doi: 10.1016/j.toxicon.2018.05.022. [Epub ahead of print] PubMed PMID: 29857089. 3: He H, Wu S, Wahome PG, Bertin MJ, Pedone AC, Beauchesne KR, Moeller PDR, Carter GT. Microcystins Containing Doubly Homologated Tyrosine Residues from a Microcystis aeruginosa Bloom: Structures and Cytotoxicity. J Nat Prod. 2018 Jun 22;81(6):1368-1375. doi: 10.1021/acs.jnatprod.7b00986. Epub 2018 May 30. PubMed PMID: 29847132. 4: Gao Y, Shimizu K, Amano C, Wang X, Pham TL, Sugiura N, Utsumi M. Response of microcystin biosynthesis and its biosynthesis gene cluster transcription in Microcystis aeruginosa on electrochemical oxidation. Environ Technol. 2018 Jun 12:1-9. doi: 10.1080/09593330.2018.1482371. [Epub ahead of print] PubMed PMID: 29806796. 5: Chen Y, Wang J, Chen X, Li D, Han X. Microcystin-leucine arginine mediates apoptosis and engulfment of Leydig cell by testicular macrophages resulting in reduced serum testosterone levels. Aquat Toxicol. 2018 Jun;199:116-126. doi: 10.1016/j.aquatox.2018.03.018. Epub 2018 Mar 17. PubMed PMID: 29621671. 6: Raska J, Ctverackova L, Dydowiczova A, Sovadinova I, Blaha L, Babica P. Tumor-promoting cyanotoxin microcystin-LR does not induce procarcinogenic events in adult human liver stem cells. Toxicol Appl Pharmacol. 2018 Apr 15;345:103-113. doi: 10.1016/j.taap.2018.03.011. Epub 2018 Mar 10. PubMed PMID: 29534881. 7: Chen HQ, Zhao J, Li Y, He LX, Huang YJ, Shu WQ, Cao J, Liu WB, Liu JY. Gene expression network regulated by DNA methylation and microRNA during microcystin-leucine arginine induced malignant transformation in human hepatocyte L02 cells. Toxicol Lett. 2018 Jun 1;289:42-53. doi: 10.1016/j.toxlet.2018.03.003. Epub 2018 Mar 5. PubMed PMID: 29518473. 8: Wu X, Wu H, Wang S, Wang Y, Zhang R, Hu X, Ye J. Effect of propionamide on the growth of Microcystis flos-aquae colonies and the underlying physiological mechanisms. Sci Total Environ. 2018 Jul 15;630:526-535. doi: 10.1016/j.scitotenv.2018.02.217. Epub 2018 Feb 24. PubMed PMID: 29486445. 9: Lvova L, Guanais Gonçalves C, Prodi L, Lombardo M, Zaccheroni N, Viaggiu E, Congestri R, Guzzella L, Pozzoni F, Di Natale C, Paolesse R. Non-enzymatic portable optical sensors for microcystin-LR. Chem Commun (Camb). 2018 Mar 13;54(22):2747-2750. doi: 10.1039/c7cc09830h. PubMed PMID: 29479587. 10: Dexter J, Dziga D, Lv J, Zhu J, Strzalka W, Maksylewicz A, Maroszek M, Marek S, Fu P. Heterologous expression of mlrA in a photoautotrophic host - Engineering cyanobacteria to degrade microcystins. Environ Pollut. 2018 Jun;237:926-935. doi: 10.1016/j.envpol.2018.01.071. Epub 2018 Feb 15. PubMed PMID: 29454496. 11: Xu L, Li T, Ding W, Cao Y, Ge X, Wang Y. Combined seven miRNAs for early hepatocellular carcinoma detection with chronic low-dose exposure to microcystin-LR in mice. Sci Total Environ. 2018 Jul 1;628-629:271-281. doi: 10.1016/j.scitotenv.2018.02.021. Epub 2018 Feb 13. PubMed PMID: 29438936. 12: Jia X, Liu Z, Lu X, Tang J, Wu Y, Du Q, He J, Zhang X, Jiang J, Liu W, Zheng Y, Ding Y, Zhu W, Zhang H. Effects of MCLR exposure on sex hormone synthesis and reproduction-related genes expression of testis in male Rana nigromaculata. Environ Pollut. 2018 May;236:12-20. doi: 10.1016/j.envpol.2018.01.057. PubMed PMID: 29414332. 13: Zhu Q, Wang Z, Zhou L, Ren Y, Gong Y, Qin W, Bai L, Hu J, Wang T. The role of cadherin-11 in microcystin-LR-induced migration and invasion in colorectal carcinoma cells. Oncol Lett. 2018 Feb;15(2):1417-1422. doi: 10.3892/ol.2017.7458. Epub 2017 Nov 21. PubMed PMID: 29399188; PubMed Central PMCID: PMC5774544. 14: Xu C, Yang Y, Liu L, Li J, Liu X, Zhang X, Liu Y, Zhang C, Liu X. Microcystin-LR nanobody screening from an alpaca phage display nanobody library and its expression and application. Ecotoxicol Environ Saf. 2018 Apr 30;151:220-227. doi: 10.1016/j.ecoenv.2018.01.003. Epub 2018 Jan 30. PubMed PMID: 29353171. 15: Shen F, Wang L, Zhou Q, Huang X. Effects of lanthanum on Microcystis aeruginosa: Attention to the changes in composition and content of cellular microcystins. Aquat Toxicol. 2018 Mar;196:9-16. doi: 10.1016/j.aquatox.2018.01.007. Epub 2018 Jan 6. PubMed PMID: 29324395. 16: Qian H, Liu G, Lu T, Sun L. Developmental neurotoxicity of Microcystis aeruginosa in the early life stages of zebrafish. Ecotoxicol Environ Saf. 2018 Apr 30;151:35-41. doi: 10.1016/j.ecoenv.2017.12.059. Epub 2018 Jan 2. PubMed PMID: 29304416. 17: Lin W, Hou J, Guo H, Li L, Wang L, Zhang D, Li D, Tang R. The synergistic effects of waterborne microcystin-LR and nitrite on hepatic pathological damage, lipid peroxidation and antioxidant responses of male zebrafish. Environ Pollut. 2018 Apr;235:197-206. doi: 10.1016/j.envpol.2017.12.059. Epub 2018 Jan 4. PubMed PMID: 29289830. 18: Milotic M, Milotic D, Koprivnikar J. Exposure to a cyanobacterial toxin increases larval amphibian susceptibility to parasitism. Parasitol Res. 2018 Feb;117(2):513-520. doi: 10.1007/s00436-017-5727-0. Epub 2017 Dec 21. PubMed PMID: 29270769. 19: Yang S, Chen L, Wen C, Zhang X, Feng X, Yang F. MicroRNA expression profiling involved in MC-LR-induced hepatotoxicity using high-throughput sequencing analysis. J Toxicol Environ Health A. 2018;81(5):89-97. doi: 10.1080/15287394.2017.1415580. Epub 2017 Dec 21. PubMed PMID: 29265921. 20: Ma J, Li Y, Wu M, Li X. Oxidative stress-mediated p53/p21(WAF1/CIP1) pathway may be involved in microcystin-LR-induced cytotoxicity in HepG2 cells. Chemosphere. 2018 Mar;194:773-783. doi: 10.1016/j.chemosphere.2017.12.051. Epub 2017 Dec 22. PubMed PMID: 29248874.