Cited in several environment-related research articles
Cylindrospermopsin is a tricyclic alkaloid hepatotoxin produced by cyanobacteria. Cylindrospermopsin exhibits a completely different mechanism of toxicity than microcystins by targeting/inhibiting the synthesis of glutathione, proteins, and pyrimidine nucleotides. Cylindrospermopsin is considered to be genotoxic. It was shown to break double stranded DNA and reduce cell viability in HepG2 cells.
Product Details
Alternative Name:
EN-Cylindrospermopsin
Formula:
C15H21N5O7S
MW:
415.4
Source:
Isolated from Cylindrospermopsis raciborskii.
CAS:
143545-90-8
RTECS:
UV9104310
Purity:
≥95% (HPLC)
Identity:
Identity determined by MS.
Appearance:
Glassy solid.
Solubility:
Soluble in DMSO, 100% methanol, or water.
Shipping:
Ambient
Long Term Storage:
-20°C
Scientific Background:
Cyanobacteria are photosynthetic prokaryotes mostly present in freshwater ecosystems. The increasingly frequent appearance of cyanobacteria blooms in lakes and rivers is linked to climate changes and human activities. Microcystins are a group of cyclic heptapeptide hepatotoxins produced by a number of cyanobacterial genera. The most notable of which, and namesake, is the widespread genus Microcystis. Structurally, all microcystins consist of the generalized structure cyclo(-D-Ala1-X2-D-MeAsp3-Y4-Adda5-D-Glu6-Mdha7-). X and Y are variable L-amino acids, D-MeAsp is D-erythro-β-methylaspartic acid and Mdha is N-methyldehydroalanine. Adda is the cyanobacteria unique C20 β-amino acid 3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid. Substitutions of the variable L-amino acids at positions 2 and 4 give rise to at least 21 known primary microcystin analogs and alterations in the other constituent amino acids result in more than 90 reported mycrocystins to date.
Regulatory Status:
RUO - Research Use Only
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Product Literature References
In Vitro Toxicity Evaluation of Cyanotoxins Cylindrospermopsin and Microcystin-LR on Human Kidney HEK293 Cells: L.D. Quijada, et al.; Toxins 14, 429 (2022), Abstract;
The cyanotoxin cylindrospermopsin slows down cell cycle progression and extends metaphase duration in immortalised human airway epithelial cells: J. Vennmann, et al.; Toxicon 209, 28 (2022), Abstract;
Treatment of cylindrospermopsin by hydroxyl and sulfate radicals: Does degradation equal detoxification?: M. Schneider, et al.; J. Hazard. Mater. 424, 127447 (2022), Abstract;
Influence of refrigeration and freezing in Microcystins and Cylindrospermopsin concentrations on fish muscle of tilapia (Oreochromis niloticus) and tench (Tinca tinca): L. Diez-Quijada, et al.; Food Chem. Toxicol. 158, 112673 (2021), Abstract;
Multibiomarker-based assessment of toxicity of central European strains of filamentous cyanobacteria Aphanizomenon gracile and Raphidiopsis raciborskii to zebrafish Danio rerio: H. Falfushynska, et al.; Water Res. 194, 116923 (2021), Abstract;
Cylindrospermopsin induced changes in growth, toxin production and antioxidant response of Acutodesmus acuminatus and Microcystis aeruginosa under differing light and nitrogen conditions: M.A. Chia, et al.; Ecotoxicol. Environ. Saf. 142, 189 (2017), Abstract;
Intestinal transport of Cylindrospermopsin using the Caco-2 cell line: S. Pichardo; Toxicol. In Vitro 38, 142 (2017), Application(s): Creation of stock solution of CYN, Abstract;
Cyanotoxins at low doses induce apoptosis and inflammatory effects in murine brain cells: potential implications for neurodegenerative diseases: L. Takser, et al.; Toxicol. Rep. 3, 180 (2016), Application(s): Cell culture, Abstract;
Inability to detect free cylindrospermopsin in spiked aquatic organism extracts plausibly suggests protein binding: M. Esterhyuzen-Londt, et al.; Toxicon. 122, 89 (2016), Application(s): Cell culture, Abstract;
Oxidative stress responses in the animal model, Daphnia pulex exposed to a natural bloom extract versus artificial cyanotoxin mixtures: M. Esterhuizen-Londt, et al.; Aquat. Toxicol. 179, 151 (2016), Abstract;
Beneficial effects of vitamin E supplementation against the oxidative stress on Cylindrospermopsin-exposed tilapia (Oreochromis niloticus): R. Guzman-Guillen, et al.; Toxicon 104, 34 (2015), Abstract;
Cylindrospermopsin induces neurotoxicity in tilapia fish (Oreochromis niloticus) exposed to Aphanizomenon ovalisporum: R. Guzmán-Guillén, et al.; Aquat. Toxicol. 161C, 17 (2015), Abstract;
Effects of microcystin-LR, cylindrospermopsin and a microcystin-LR/cylindrospermopsin mixture on growth, oxidative stress and mineral content in lettuce plants (Lactuca sativa L.): M. Freitas, et al.; Ecotoxicol. Environ. Saf. 116, 59 (2015), Application(s): HPLC, Exposure to lettuce plants, Abstract;
Toxin Resistance in Aquatic Fungi Poses Environmentally Friendly Remediation Possibilities: A Study on the Growth Responses and Biosorption Potential of Mucor hiemalis EH5 against Cyanobacterial Toxins: E. Balsano, et al.; Int. J. Water Wastewater Treat. 1, (2015), Full Text
Cylindrospermopsin degradation in sediments - The role of temperature, redox conditions, and dissolved organic carbon: S. Klitzke & J. Fastner; Water Res. 46, 1549 (2012), Abstract;
Time-dependent histopathological changes induced in Tilapia (Oreochromis niloticus) after acute exposure to pure cylindrospermopsin by oral and intraperitoneal route: D. Gutierrez-Praena, et al.; Ecotoxicol. Environ. Saf. 76, 102 (2012), Abstract;
Acute effects of pure cylindrospermopsin on the activity and transcription of antioxidant enzymes in tilapia (Oreochromis niloticus) exposed by gavage: M. Puerto, et al.; Ecotoxicology 20, 1852 (2011), Abstract;
Modulation of gap-junctional intercellular communication by a series of cyanobacterial samples from nature and laboratory cultures: K. Novakova, et al.; Toxicon 58, 76 (2011), Abstract;
Inhibition of gap-junctional intercellular communication and activation of mitogen-activated protein kinases by cyanobacterial extracts--indications of novel tumor-promoting cyanotoxins?: L. Blaha, et al.; Toxicon 55, 126 (2010), Abstract; Full Text
The cyanobacterial toxin cylindrospermopsin inhibits pyrimidine nucleotide synthesis and alters cholesterol distribution in mice: M. Reisner, et al.; Toxicol. Sci. 82, 620 (2004), Abstract;
The Palm Island mystery disease 20 years on: a review of research on the cyanotoxin cylindrospermopsin: D.J. Griffiths and M.L. Saker; Environ. Toxicol. 18, 78 (2003), Review, Abstract;
Preliminary evidence for in vivo tumour initiation by oral administration of extracts of the blue-green alga cylindrospermopsis raciborskii containing the toxin cylindrospermopsin: I.R. Falconer & A.R. Humpage; Environ. Toxicol. 16, 192 (2001), Abstract;
Cylindrospermopsin, a cyanobacterial alkaloid: evaluation of its toxicologic activity: G.R. Shaw, et al.; Ther. Drug Monit. 22, 89 (2000), Abstract;
Isolation and toxicity of Cylindrospermopsis raciborskii from an ornamental lake: P.R. Hawkins, et al.; Toxicon. 35, 341 (1997), Abstract;
Cylindrospermopsin, a potent hepatotoxin from the blue-green alga Cylindrospermopsis raciborskii: I. Ohtani, et al.; JACS 114, 7941 (1992), Full Text
Severe hepatotoxicity caused by the tropical cyanobacterium (blue-green alga) Cylindrospermopsis raciborskii (Woloszynska) Seenaya and Subba Raju isolated from a domestic water supply reservoir: P.R. Hawkins, et al.; Appl. Environ. Microbiol. 50, 1292 (1985), Abstract; Full Text
