Cylindrospermopsin

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Description

Cylindrospermopsin is a tricyclic alkaloid hepatotoxin synthesized by certain species of cyanobacteria. This compound is characterized as a polycyclic uracil derivative, which includes guanidino and sulfate functional groups. It is also a zwitterionic ion and therefore highly water soluble. Cylindrospermopsin primarily targets liver and kidney tissues, exerting its toxic effects mainly through the inhibition of protein synthesis and the covalent modification of DNA and RNA. In addition, cylindrosporine is considered to be potentially genotoxic.

Specification

Item	Cylindrospermopsin
Catalog	MC143545908
CAS	143545-90-8
Molecular Formula	C₁₅H₂₁N₅O₇S
Molecular Weight	415.42
Purity	>95%
Solubility	Soluble in DMSO, 100% methanol, or water.
Appearance	White powder
Source	Isolated from Cylindrospermopsis raciborskii.
MDL Number	MFCD01939922
SMILES	C[C@H]1[C@H](C[C@@H]2C[C@@H](N=C3NC[C@H]1N23)[C@@H](O)C4=CC(=O)NC(=O)N4)OS(=O)(=O)O
InChi Code	InChI=1S/C15H21N5O7S/c1-6-10-5-16-14-17-8(13(22)9-4-12(21)19-15(23)18-9)2-7(20(10)14)3-11(6)27-28(24,25)26/h4,6-8,10-11,13,22H,2-3,5H2,1H3,(H,16,17)(H,24,25,26)(H2,18,19,21,23)/t6-,7+,8-,10-,11+,13-/m1/s1
InChi Key	LHJPHMKIGRLKDR-VDPNAHCISA-N
Storage Temperature	Store at -10 °C to -25 °C. Protect from moisture and strong direct light.

Biochemical Pathways

Cylindrospermopsin is a potent toxin that contributes to oxidative damage by elevating levels of reactive oxygen species (ROS) within cells. This increase in ROS is accompanied by a decrease in glutathione (GSH) levels, along with a reduction in the synthesis of crucial antioxidant catalysts and heme carriers. In addition to its effects on oxidative stress, cylindrospermopsin exhibits neurotoxicity by impairing the function of acetylcholinesterase (AChE) and muscarinic acetylcholine receptors (CHRM), which are vital for neurotransmission. Furthermore, this toxin disrupts cellular energy metabolism by significantly interfering with the intermediate enzymes involved in oxidative phosphorylation.

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For Research Use Only. Not for use in diagnostic or therapeutic procedures.