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Microcystin-LR

(Synonyms: 微囊藻毒素(LR亚型),Cyanoginosin-LR; MC-LR; Toxin T 17 (Microcystis aeruginosa)) 目录号 : GC36607

A potent protein phosphatase inhibitor

Microcystin-LR Chemical Structure

Cas No.:101043-37-2

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50 µg(0.5 mM * 100 µL in Ethanol)
¥1,935.00
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100 µg(0.5 mM * 200 µL in Ethanol)
¥3,285.00
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产品描述

Microcystins are hepatotoxic cyclic heptapeptide toxins produced by cyanobacteria.1 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.2 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.

1.Rinehart, K.L., Harada, K.-i., Namikoshi, M., et al.Nodularin, microcystin, and the configuration of AddaJ. Am. Chem. Soc.110(25)8557-8558(1988) 2.Honkanen, R.E., Zwiller, J., Moore, R.E., et al.Characterization of microcystin-LR, a potent inhibitor of Type 1 and Type 2A protein phosphatasesJ. Biol. Chem.265(32)19401-19404(1990)

Chemical Properties

Cas No. 101043-37-2 SDF
别名 微囊藻毒素(LR亚型),Cyanoginosin-LR; MC-LR; Toxin T 17 (Microcystis aeruginosa)
化学名 cyclo[2,3-didehydro-N-methylalanyl-D-alanyl-L-leucyl-(3S)-3-methyl-D-β-aspartyl-L-arginyl-(2S,3S,4E,6E,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoyl-D-γ-glutamyl]
Canonical SMILES CC(/C=C/[C@@H]([C@@H](C(N[C@H](CCC(N(C(C(N[C@@H]1C)=O)=C)C)=O)C(O)=O)=O)C)NC([C@@H](NC([C@H]([C@@H](NC([C@](NC1=O)([H])CC(C)C)=O)C(O)=O)C)=O)CCCNC(N)=N)=O)=C\[C@H](C)[C@@H](OC)CC2=CC=CC=C2
分子式 C49H74N10O12 分子量 995.2
溶解度 DMSO: 10 mg/ml,Ethanol: 10 mg/ml,Methanol: 10 mg/ml 储存条件 Store at -20°C, protect from light
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Research Update

Microcystin-LR ameliorates pulmonary fibrosis via modulating CD206+ M2-like macrophage polarization

Cell Death Dis 2020 Feb 19;11(2):136.PMID:32075954DOI:10.1038/s41419-020-2329-z.

Idiopathic pulmonary fibrosis (IPF) is a group of chronic interstitial pulmonary diseases characterized by myofibroblast proliferation and extracellular matrix deposition with limited treatment options. Based on our previous observation, we hypothesized microcystin-leucine arginine (LR), an environmental cyanobacterial toxin, could potentially suppress pulmonary fibrosis. In this study, we first demonstrated that chronic exposure of Microcystin-LR by oral for weeks indeed attenuated the pulmonary fibrosis both on bleomycin-induced rat and fluorescein isothiocyanate-induced mouse models. Our data further indicated that treatment with Microcystin-LR substantially reduced TGF-β1/Smad signaling in rat pulmonary tissues. The experiments in vitro found that Microcystin-LR was capable of blocking epithelial-mesenchymal transition (EMT) and fibroblast-myofibroblast transition (FMT) through suppressing the differentiation of CD206+ macrophages. Mechanically, Microcystin-LR was found to bind to glucose-regulated protein 78 kDa (GRP78) and suppress endoplasmic reticulum unfolded protein response (UPRER) signaling pathways. These events led to the modulation of M2 polarization of macrophages, which eventually contributed to the alleviation of pulmonary fibrosis. Our results revealed a novel mechanism that may account for therapeutic effect of Microcystin-LR on IPF.

The latest advances in the reproductive toxicity of Microcystin-LR

Environ Res 2021 Jan;192:110254.PMID:32991922DOI:10.1016/j.envres.2020.110254.

Microcystin-LR (MC-LR) is an emerging environmental pollutant produced by cyanobacteria that poses a threat to wild life and human health. In recent years, the reproductive toxicity of MC-LR has gained widespread attention, a large number of toxicological studies have filled the gaps in past research and more molecular mechanisms have been elucidated. Hence, this paper reviews the latest research advances on MC-LR-induced reproductive toxicity. MC-LR can damage the structure and function of the testis, ovary, prostate, placenta and other organs of animals and then reduce their fertility. Meanwhile, MC-LR can also be transmitted through the placenta to the offspring causing trans-generational and developmental toxicity including death, malformation, growth retardation, and organ dysfunction in embryos and juveniles. The mechanisms of MC-LR-induced reproductive toxicity mainly include the inhibition of protein phosphatase 1/2 A (PP1/2 A) activity and the induction of oxidative stress. On the one hand, MC-LR triggers the hyperphosphorylation of certain proteins by inhibiting intracellular PP1/2 A activity, thereby activating multiple signaling pathways that cause inflammation and blood-testis barrier destruction, etc. On the other hand, MC-LR-induced oxidative stress can result in cell programmed death via the mitochondrial and endoplasmic reticulum pathways. It is worth noting that epigenetic modifications are also involved in reproductive cell apoptosis, which may be an important direction for future research. Furthermore, this paper proposes for the first time that MC-LR can produce estrogenic effects in animals as an environmental estrogen. New findings and suggestions in this review could be areas of interest for future research.

Photocatalytic degradation of Microcystin-LR by modified TiO2 photocatalysis: A review

Sci Total Environ 2020 Nov 15;743:140694.PMID:32673915DOI:10.1016/j.scitotenv.2020.140694.

Microcystin-LR (MC-LR), the most toxic and commonly encountered cyanotoxin, is produced by harmful cyanobacterial blooms and potentially threatens human and ecosystems health. Titanium dioxide (TiO2) photocatalysis is attracting growing attention and has been considered as an efficient, environmentally friendly and promising solution to eliminate MC-LR in the aquatic ecosystems. Over recent decades, scientific efforts have been directed towards the understanding of fundamentals, modification strategies, and application potentials of TiO2 photocatalysis in degrading MC-LR. In this article, recent reports have been reviewed and progress has been summarized in the development of heterogeneous TiO2-based photocatalysts for MC-LR photodegradation under visible, UV, or solar light. The proposed photocatalytic principles of TiO2 and destruction of MC-LR have been thoroughly discussed. Specifically, some main modification methods for improving the drawbacks and performance of TiO2 nanoparticle were highlighted, including element doping, semiconductor coupling, immobilization, floatability amelioration and magnetic separation. Moreover, the performance evaluation metrics quantum yield (QY) and figure of merit (FOM) were used to compare different photocatalysts in MC-LR degradation. The best performance was seen in N-TiO2 with QY and FOM values of 2.20E-07 molecules/photon and 1.00E-11 mol·L/(g·J·h). N-TiO2 or N-TiO2-based materials may be excellent options for photocatalyst design in terms of MC-LR degradation. Finally, a summary of the remaining challenges and perspectives on new tendencies in this exciting frontier and still an emerging area of research were addressed accordingly. Overall, the present review will offer a deep insight for understanding the photodegradation of MC-LR with modified TiO2 to further inspire researchers that work in associated fields.

Immunoassay technology: Research progress in Microcystin-LR detection in water samples

J Hazard Mater 2022 Feb 15;424(Pt B):127406.PMID:34689091DOI:10.1016/j.jhazmat.2021.127406.

Increasing global warming and eutrophication have led to frequent outbreaks of cyanobacteria blooms in freshwater. Cyanobacteria blooms cause the death of aquatic and terrestrial organisms and have attracted considerable attention since the 19th century. Microcystin-LR (MC-LR) is one of the most typical cyanobacterial toxins. Therefore, the fast, sensitive, and accurate determination of MC-LR plays an important role in the health of humans and animals. Immunoassay refers to a method that uses the principle of immunology to determine the content of the tested substance in a sample using the tested substance as an antigen or antibody. In analytical applications, the immunoassay technology could use the specific recognition of antibodies for MC-LR detection. In this review, we firstly highlight the immunoassay detection of MC-LR over the past two decades, including classical enzyme-link immunosorbent assay (ELISA), modern immunoassay with optical signal, and modern immunoassay with electrical signal. Among these detection methods, the water environment was used as the main detection system. The advantages and disadvantages of the different detection methods were compared and analyzed, and the principles and applications of immunoassays in water samples were elaborated. Furthermore, the current challenges and developmental trends in immunoassay were systematically introduced to enhance MC-LR detection performance, and some critical points were given to deal with current challenges. This review provides novel insight into MC-LR detection based on immunoassay method.

Determination of Microcystin-LR, employing aptasensors

Biosens Bioelectron 2018 Nov 15;119:110-118.PMID:30121422DOI:10.1016/j.bios.2018.08.003.

Cyanobacteria produce toxins such as Microcystin-LR (MC-LR), which are associated with potential hepatotoxicity in humans. The detection of cyanobacteria and their toxins in drinking water and sea food is therefore crucial. To date, methods such as high performance liquid chromatography (HPLC), protein phosphatase inhibition assay (PPIA), and Raman spectroscopy have been employed to monitor MC-LR levels. Although these techniques are precise and sensitive, they require expensive instrumentation, well-trained personnel and involve time-consuming processes meaning that their application is generally limited to well-resourced, centralised laboratory facilities. Among the emerging MC-LR detection methods, aptasensors have received great attention because of their remarkable sensitivity, selectivity, and simplicity. Aptamers, also known as "chemical" or "artificial antibodies", serve as the recognition moieties in aptasensors. This review explores the current state-of-the-art of MC-LR aptasensor platforms, evaluating the advantages and, limitations of typical transduction technologies to identify the most efficient detection system for the potentially harmful cyanobacteria associated toxin.