246032-59-7

Basic information

• Product Name: methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin
• Synonyms: methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin
• CAS NO: 246032-59-7
• Molecular Weight: 703.659
• Mol File: 246032-59-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin(246032-59-7)
• EPA Substance Registry System: methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin(246032-59-7)

Safety Data

• Hazardous Substances Data: 246032-59-7(Hazardous Substances Data)

Upstream product

• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 148579-57-1 (2S,3R,4S,5S,6S)-2-(4-(hydroxymethyl)phenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 148579-56-0 (2S,3R,4S,5S,6S)-2-(4-formylphenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 6919-98-8 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester 
• 246032-58-6 methyl 1-(4-hydroxymethylphenyl)-β-D-glucopyranuronate 
• 91421-43-1 9-amino-20(S)-camptothecin 
• 82228-14-6 methyl D-glucopyranuronate 
• 32449-92-6 D-glucurono-6,3-lactone 

Relevant articles and documents

Design and synthesis of water-soluble glucuronide derivatives of camptothecin for cancer prodrug monotherapy and antibody-directed enzyme prodrug therapy (ADEPT)

Glucuronide prodrugs of 9-aminocamptothecin were synthesized. Prodrug 4, in which 9-aminocamptothecin was-connected to glucuronic acid by an aromatic spacer via a carbamate linkage, was stable in both aqueous solution and human plasma. Prodrug 4 and its potassium salt 12 were 20-80-fold less toxic than 9-aminocamptothecin to human tumor cell lines. The simultaneous addition of β-glucuronidase and 4 or 12 to tumor cells resulted in a cytotoxic effect equal to that of 9-aminocamptothecin alone. Prodrugs 4 and 12 were over 80 and 4000 times more soluble than 9-aminocamptothecin in aqueous solutions at pH 4.0, respectively. Compounds 4 and 12 may be useful for prodrug monotherapy of tumors that accumulate extracellular lysosomal β- glucuronidase as well as for antibody-directed enzyme prodrug-therapy (ADEPT) of cancer.