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143545-90-8

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  • 2,4(1H,3H)-Pyrimidinedione,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]-

    Cas No: 143545-90-8

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  • 2,4(1H,3H)-Pyrimidinedione,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]-

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  • 2,4(1H,3H)-Pyrimidinedione,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]-

    Cas No: 143545-90-8

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143545-90-8 Usage

Description

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. It has been shown to inhibit the activity of the uridine monophosphate synthase complex with a Ki value of 10 μM. 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.

Uses

Cylindrospermopsin is a cyanotoxin produced by cyanobacterial species and found in many bodies of water.

Definition

ChEBI: A triazaacenaphthylene that is 2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triazaacenaphthylene which is substituted at positions 3, 4, and 7 by methyl, sulfooxy, and (2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)(hydroxy)methyl groups, respecti ely (the 2aS,3R,4S,5aS,7R stereoisomer in which the carbon bearing the hydroxy group has R configuration). It is a cyanotoxin produced by several species f freshwater cyanobacteria, such as Aphanizomenon ovalisporum.

Check Digit Verification of cas no

The CAS Registry Mumber 143545-90-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,3,5,4 and 5 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 143545-90:
(8*1)+(7*4)+(6*3)+(5*5)+(4*4)+(3*5)+(2*9)+(1*0)=128
128 % 10 = 8
So 143545-90-8 is a valid CAS Registry Number.
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

143545-90-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name cylindrospermopsin

1.2 Other means of identification

Product number -
Other names Cylindrospermopsin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:143545-90-8 SDS

143545-90-8Upstream product

143545-90-8Downstream Products

143545-90-8Relevant articles and documents

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

Mailyan, Artur K.,Chen, Joanna L.,Li, Weiwei,Keller, Arturo A.,Sternisha, Shawn M.,Miller, Brian G.,Zakarian, Armen

supporting information, p. 6027 - 6032 (2018/05/05)

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

White, James D.,Hansen, Joshua D.

, p. 1963 - 1977 (2007/10/03)

(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.

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