Cylindrospermopsin
(Synonyms: 柱孢藻毒素) 目录号 : GC43351A cyanotoxin
Cas No.:143545-90-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cylindrospermopsin, a tricyclic uracil derivative, is a cyanobacterial toxin that was first discovered in an algal bloom contaminating a local drinking supply on Palm Island in Queensland, Australia after an outbreak of a mysterious disease. Cylindrospermopsin targets protein and glutathione synthesis in hepatocytes (IC50s = 1.3 and 2.4 µM, respectively), leading to cell death. [1] It has been shown to inhibit the activity of the uridine monophosphate synthase complex with a Ki value of 10 µM.[2] Cylindrospermopsin is genotoxic, inducing DNA damage as evidenced by double strand breaks and reducing cell viability in HepG2 cells at 0.1-0.5 µg/ml.[3]
Reference:
[1]. Runnegar, M.T., Xie, C., Snider, B.B., et al. In vitro hepatotoxicity of the cyanobacterial alkaloid cylindrospermopsin and related synthetic analogues. Toxicological Sciences 67, 81-87 (2002).
[2]. Reisner, M., Carmeli, S., Werman, M., et al. The cyanobacterial toxin cylindrospermopsin inhibits pyrimidine nucleotide synthesis and alters cholesterol distribution in mice. Toxicological Sciences 82, 620-627 (2004).
[3]. Straser, A., Filipic, M., Novak, M., et al. Double strand breaks and cell-cycle arrest induced by the cyanobacterial toxin cylindrospermopsin in HepG2 cells. Mar.Drugs 11(8), 3077-3090 (2013).
| Cas No. | 143545-90-8 | SDF | |
| 别名 | 柱孢藻毒素 | ||
| 化学名 | 6-[(R)-hydroxy[(2aS,3R,4S,5aS,7R)-2,2a,3,4,5,5a,6,7-octahydro-3-methyl-4-(sulfooxy)-1H-1,8,8b-triazaacenaphthylen-7-yl]methyl]-2,4(1H,3H)-pyrimidinedione | ||
| Canonical SMILES | C[C@H]1[C@@H](OS(=O)(O)=O)C[C@@]2([H])N(C3=N[C@]([C@@H](O)C(N([H])C(N4[H])=O)=CC4=O)([H])C2)[C@@]1(CN3)[H] | ||
| 分子式 | C15H21N5O7S | 分子量 | 415.4 |
| 溶解度 | Soluble in DMSO, Methanol, Water | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.4073 mL | 12.0366 mL | 24.0732 mL |
| 5 mM | 0.4815 mL | 2.4073 mL | 4.8146 mL |
| 10 mM | 0.2407 mL | 1.2037 mL | 2.4073 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Cyanotoxin Cylindrospermopsin producers and the catalytic decomposition process: A review
Harmful Algae 2020 Sep;98:101894.PMID:33129452DOI:10.1016/j.hal.2020.101894.
Cylindrospermopsin (CYN) is a toxic secondary metabolite produced by several freshwater species of cyanobacteria. Its high chemical stability and wide biological activity pose a series of threats for human and animal morbidity and mortality. The biggest risk of CYN exposure for human organism comes from the consumption of contaminated water, fish or seafood. Very important for effective monitoring of the occurrence of CYN in aquatic environment is accurate identification of cyanobacteria species, that are potentially able to synthesize CYN. In this review we collect data about the discovery of CYN production in cyanobacteria and present the morphological changes between all its producers. Additionally we set together the results describing the catalytic decomposition of CYN.
Cylindrospermopsin impairs zebrafish (Danio rerio) embryo development
Mar Environ Res 2022 Mar;175:105567.PMID:35123182DOI:10.1016/j.marenvres.2022.105567.
Cyanotoxins are among common contaminants that can impair human, animal, and environmental health. Cylindrospermopsin (CYN) is an abundant form of cyanotoxins elevated following algal bloom in the water worldwide. Previous studies have described CYN effects on several organs in mammals. However, little is known about its toxicity mechanisms in other vertebrates. This study aims to characterize the developmental effects of CYN using zebrafish larvae as an aquatic model organism. A wide range of CYN concentrations (0-2000 μg/L) was tested using a morphometric approach for survival, hatching, various growth and developmental abnormalities. We also investigated the expression of genes related to oxidative stress, osmoregulation, and thyroid function. Exposure to CYN resulted in decreased growth, increased developmental abnormalities such as pericardial and yolk sac edema as well as swim bladder absence. In addition, CYN increased tr1a, and decreased dio1 and dio3 transcript levels which are involved in thyroid-mediated function. It also increased transcript levels related to oxidative stress, including hsp70, ahr1a, cyp1a, gpx and cat. Lastly, CYN exposure increased aqp3a and decreased dab2, which are involved in osmoregulation with a threshold of 10 μg/L. The present study demonstrates multiple effects of exposure to environmentally relevant CYN concentrations in zebrafish embryos.
Immunotoxic Effects Induced by Microcystins and Cylindrospermopsin: A Review
Toxins (Basel) 2021 Oct 8;13(10):711.PMID:34679003DOI:10.3390/toxins13100711.
Cyanotoxin occurrence is gaining importance due to anthropogenic activities, climate change and eutrophication. Among them, Microcystins (MCs) and Cylindrospermopsin (CYN) are the most frequently studied due to their ubiquity and toxicity. Although MCs are primary classified as hepatotoxins and CYN as a cytotoxin, they have been shown to induce deleterious effects in a wide range of organs. However, their effects on the immune system are as yet scarcely investigated. Thus, to know the impact of cyanotoxins on the immune system, due to its importance in organisms' homeostasis, is considered of interest. A review of the scientific literature dealing with the immunotoxicity of MCs and CYN has been performed, and both in vitro and in vivo studies have been considered. Results have confirmed the scarcity of reports on the topic, particularly for CYN. Decreased cell viability, apoptosis or altered functions of immune cells, and changed levels and mRNA expression of cytokines are among the most common effects reported. Underlying mechanisms, however, are still not yet fully elucidated. Further research is needed in order to have a full picture of cyanotoxin immunotoxicity.
Biosynthesis of Cylindrospermopsin in Cyanobacteria: Characterization of CyrJ the Sulfotransferase
J Nat Prod 2021 Feb 26;84(2):408-416.PMID:33439646DOI:10.1021/acs.jnatprod.0c01089.
7-Deoxy-desulfo-cylindrospermopsin was purified at small-scale from the supernatant of a culture of the cyanobacterium Oscillatoria sp. PCC 10702. This metabolite was obtained in a pure form using a three-step chromatographic procedure, and its identity was confirmed by liquid chromatography-tandem mass spectrometry (LC-MS/MS). LC-MS quantification showed that this metabolite was excreted in the culture medium of Oscillatoria sp. PCC 10702. Isotopic incorporation studies using [2-13C,15N]glycine, a Cylindrospermopsin precursor, and Oscillatoria sp. PCC 10702 cells showed that glycine was incorporated into 7-deoxy-desulfo-cylindrospermopsin, 7-deoxy-cylindrospermopsin, 7-epi-cylindrospermopsin, and Cylindrospermopsin. The isotopic incorporation rate was consistent with the following metabolic flux: 7-deoxy-desulfo-cylindrospermopsin → 7-deoxy-cylindrospermopsin → 7-epi-cylindrospermopsin and Cylindrospermopsin. We have cloned the cyrJ gene into an expression vector and overproduced the putative sulfotransferase CyrJ in Escherichia coli. The purified protein CyrJ catalyzed, in vitro, the transfer of a sulfonate group from 3'-phosphoadenosine-5'-phosphosulfate (PAPS) to 7-deoxy-desulfo-cylindrospermopsin to give 7-deoxy-cylindrospermopsin. Kinetic analysis afforded the following apparent constants: KM app. (PAPS) = 0.12 μM, Vmax app. = 20 nM/min, KM app. (7-deoxy-desulfo-cylindrospermopsin) = 0.12 μM, and KI app. (7-deoxy-desulfo-cylindrospermopsin) = 4.1 μM. Preliminary data suggested that CyrJ catalyzed the reaction through a ternary-complex kinetic mechanism. All these data confirmed that CyrJ catalyzed a sulfotransfer during the penultimate step of the biosynthesis of Cylindrospermopsin.
Neurotoxicity induced by microcystins and Cylindrospermopsin: A review
Sci Total Environ 2019 Jun 10;668:547-565.PMID:30856566DOI:10.1016/j.scitotenv.2019.02.426.
Microcystins (MCs) and Cylindrospermopsin (CYN) are among the most frequent toxins produced by cyanobacteria. These toxic secondary metabolites are classified as hepatotoxins and cytotoxin, respectively. Furthermore, both may present the ability to induce damage to the nervous system. In this sense, there are many studies manifesting the potential of MCs to cause neurotoxicity both in vitro and in vivo, due to their probable capacity to cross the blood-brain-barrier through organic anion transporting polypeptides. Moreover, the presence of MCs has been detected in brain of several experimental models. Among the neurological effects, histopathological brain changes, deregulation of biochemical parameters in brain (production of oxidative stress and inhibition of protein phosphatases) and behavioral alterations have been described. It is noteworthy that minority variants such as MC-LF and -LW have demonstrated to exert higher neurotoxic effects compared to the most studied congener, MC-LR. By contrast, the available studies concerning CYN-neurotoxic effects are very scarce, mostly showing inflammation and apoptosis in neural murine cell lines, oxidative stress, and alteration of the acetylcholinesterase activity in vivo. However, more studies are required in order to clarify the neurotoxic potential of both toxins, as well as their possible contribution to neurodegenerative diseases.