143545-90-8

Basic information

• Product Name: CYLINDROSPERMOPSIN
• Synonyms: 2,4(1h,3h)-pyrimidinedione,6-(hydroxy(2,2a,3,4,5,5a,6,7-octahydro-3-methyl-4-(;5a-alpha,7-beta(r*))-(-)-h;cylindrospermopsin;sulfooxy)-1h-1,8,8b-triazaacenaphthylen-7-yl)methyl)-,(2a-alpha,3-alpha,4-alp;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
• CAS NO: 143545-90-8
• Molecular Formula: C15H21N5O7S
• Molecular Weight: 415.425
• Mol File: 143545-90-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /white powder
• Density: 1.3937 (rough estimate)
• Refractive Index: 1.6460 (estimate)
• Storage Temp.: −20°C
• Solubility: DMSO: soluble
• CAS DataBase Reference: CYLINDROSPERMOPSIN(CAS DataBase Reference)
• NIST Chemistry Reference: CYLINDROSPERMOPSIN(143545-90-8)
• EPA Substance Registry System: CYLINDROSPERMOPSIN(143545-90-8)

Safety Data

• WGK Germany: 3
• RTECS: UV9104310
• Hazardous Substances Data: 143545-90-8(Hazardous Substances Data)

Usage

Description

Cylindrospermopsin is a tricyclic uracil derivative and 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. It is a cyanotoxin produced by several species of freshwater cyanobacteria, such as Aphanizomenon ovalisporum. Cylindrospermopsin targets protein and glutathione synthesis in hepatocytes, leading to cell death and has been shown to inhibit the activity of the uridine monophosphate synthase complex. It is also genotoxic, inducing DNA damage and reducing cell viability in HepG2 cells.

Uses

1. Used in Research and Development:
Cylindrospermopsin is used as a research compound for studying its toxic effects on hepatocytes and its potential role in causing diseases in humans and animals. The compound helps researchers understand the mechanisms of action and develop strategies to mitigate its harmful effects.
2. Used in Environmental Monitoring:
Cylindrospermopsin is used as a biomarker for detecting the presence of cyanobacterial toxins in water bodies. Monitoring the levels of cylindrospermopsin can help identify potential health risks associated with cyanobacterial blooms and inform water treatment processes to ensure safe drinking water.
3. Used in Pharmaceutical Development:
Cylindrospermopsin is used as a lead compound in the development of new drugs targeting protein and glutathione synthesis in hepatocytes. Understanding its mechanism of action can potentially lead to the development of therapeutic agents for various liver-related diseases.
4. Used in Toxicology Studies:
Cylindrospermopsin is used as a model compound in toxicology studies to investigate the effects of cyanotoxins on cellular processes and overall health. These studies contribute to the understanding of the risks associated with exposure to cyanotoxins and the development of safety guidelines for human exposure.

InChI:InChI=1/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

Upstream product

• 434308-76-6 (1'S,2'R)-2,6-dimethoxy-4-[2'-dibenzylamino-1'-(tert-butyldimethylsilanyloxy)-4'-trityloxybutyl]pyrimidine 
• 434308-80-2 C₃₄H₅₃BrN₄O₇Si 
• 434308-90-4 (3R,4aS,6S,7R,8S)-8-Azidomethyl-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-7-methyl-6-triethylsilanyloxy-octahydro-pyrido[1,2-c]pyrimidin-1-one 
• 434309-04-3 (3R,4aS,6S,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-6-hydroxy-7-methyl-octahydro-pyrido[1,2-c]pyrimidin-1-one 
• 434309-02-1 (3R,4aS,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-7-methyl-hexahydro-pyrido[1,2-c]pyrimidine-1,6-dione 
• 434308-74-4 (1'S,2'R)-2,6-dimethoxy-4-(2'-dibenzylamino-1'-hydroxy-4'-trityloxybutyl)pyrimidine 
• 434308-72-2 (R)-2,6-dimethoxy-4-(2'-dibenzylamino-4'-trityloxybutanoyl)pyrimidine 
• 434308-88-0 (3R,4aS,6S,7R,8S)-8-Azidomethyl-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-6-hydroxy-7-methyl-octahydro-pyrido[1,2-c]pyrimidin-1-one 
• 434308-86-8 JH₀₉₂₆₀₁ 
• 434308-98-2 (1'S,2'R)-2,6-dimethoxy-4-[2'-dibenzylamino-1'-(tert-butyldimethylsilanyloxy)-4'-hydroxybutyl]pyrimidine 
• 434309-00-9 (1'S,2'R)-2,6-dimethoxy-4-[2'-(tert-butyloxycarbonyl)amino-1'-(tert-butyldimethylsilanyloxy)-4'-hydroxybutyl]pyrimidine 
• 434308-70-0 (3R)-3-dibenzylamino-2-hydroxy-2-(2,6-dimethoxypyrimidin-4-yl)tetrahydrofuran 
• 434308-58-4 (3R,4S)-3-(tert-butyloxycarbonyl)amino-4-(tert-butyldimethylsilanyloxy)-4-(2,6-dimethoxypyrimidin-4-yl)butanal 
• 434308-78-8 (3R,4S)-3-Amino-4-(tert-butyl-dimethyl-silanyloxy)-4-(2,6-dimethoxy-pyrimidin-4-yl)-butan-1-ol 

Relevant articles and documents

Short Total Synthesis of [15N5]-Cylindrospermopsins from 15NH4Cl Enables Precise Quantification of Freshwater Cyanobacterial Contamination

Fresh water cyanobacterial algal blooms represent a major health risk because these organisms produce cylindrospermopsin, a toxic, structurally complex, zwitterionic uracil-guanidine alkaloid recognized by the EPA as a dangerous drinking water contaminant. At present, the ability to detect and quantify the presence of cylindrospermospin in water samples is severely hampered by the lack of an isotopically labeled standard for analytical mass spectrometry. Herein, we present a concise, scaled total synthesis of 15N cylindrospermosin from 15N ammonium chloride, which leverages a unique stereoselective intramolecular double conjugate addition step to assemble the tricyclic guanidine core. In addition to providing the first pure isotopically labeled probe for precise quantification of this potent biotoxin in fresh water sources, our results demonstrate how unique constraints associated with isotope incorporation compel novel solutions to synthesis design.

Total synthesis of (-)-7-epicylindrospermopsin, a toxic metabolite of the freshwater cyanobacterium Aphanizomenon ovalisporum, and assignment of its absolute configuration

(Chemical Equation Presented) The Z and E nitrones 38 and 39 from condensation of aldehyde 20 with hydroxylamine 36 underwent intramolecular dipolar cycloaddition to give the substituted 1-aza-7-oxobicyclo[2.2.1] heptanes 40 and 41 in a ratio of 2:1, respectively. Reductive N-O bond cleavage of 40 followed by carbonylation gave cyclic urea 47 in which inversion of the secondary alcohol was effected via an oxidation-reduction sequence. After conversion of the p-bromobenzyl ether 50 to azide 54, activation of the cyclic urea as its O-methylisourea and reduction of the azide led to spontaneous cyclization to afford the tricyclic nucleus 59 of cylindrospermopsin. Global deprotection, including hydrolysis of the 2,4-dimethyoxypyrimidine appendage to a uracil, and then monosulfation of the resultant diol 60 afforded a substance identical with natural (-)-7-epicylindrospermopsin (1). The asymmetric synthesis of (-)-7-epicylindrospermopsin defines its absolute configuration as 7S,8R,10S,12S,13R,14S.