1357156-42-3

Basic information

• Product Name: methyl 1-O-(2-difluoromethyl-4-aminophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate
• Synonyms: methyl 1-O-(2-difluoromethyl-4-aminophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate
• CAS NO: 1357156-42-3
• Molecular Weight: 475.4
• Mol File: 1357156-42-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl 1-O-(2-difluoromethyl-4-aminophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 1-O-(2-difluoromethyl-4-aminophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate(1357156-42-3)
• EPA Substance Registry System: methyl 1-O-(2-difluoromethyl-4-aminophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate(1357156-42-3)

Safety Data

• Hazardous Substances Data: 1357156-42-3(Hazardous Substances Data)

Upstream product

• 97-51-8 5-Nitrosalicylaldehyde 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 148579-83-3 (2S,3R,4S,5S,6S)-2-(2-formyl-4-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1357156-40-1 methyl 1-O-(2-difluoromethyl-4-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate 
• 63-29-6 D-glucurono-6,3-lactone 

Downstream Products

• 1357156-44-5 methyl 1-O-(2-difluoromethyl-4-aminophenyl)-β-D-glucopyranuronate 
• 1407150-79-1 methyl 1-O-(2-difluoromethyl-4-(1-bromoacetamido)phenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate 
• 1407150-80-4 1-O-(2-difluoromethyl-4-(1-(4,7,10-triscarboxymethyl-(1,4,7,10-tetraazacyclododecyl))acetamido)phenyl)-β-D-glucopyranuronate 
• 1407150-81-5 C₄₈H₇₃F₂N₅O₁₇ 
• 1407150-82-6 C₄₂H₆₇F₂N₅O₁₄ 

Relevant articles and documents

Development of a Gd(III)-based receptor-induced magnetization enhancement (RIME) contrast agent for β-glucuronidase activity profiling

β-Glucuronidase is a key lysosomal enzyme and is often overexpressed in necrotic tumor masses. We report here the synthesis of a pro receptor-induced magnetization enhancement (pro-RIME) magnetic resonance imaging (MRI) contrast agent ([Gd(DOTA-FPβGu)]) for molecular imaging of ss-glucuronidase activity in tumor tissues. The contrast agent consists of two parts, a gadolinium complex and a β-glucuronidase substrate (β-D- glucopyranuronic acid). The binding association constant (KA) of [Gd(DOTA-FPβGu)] is 7.42 × 102, which is significantly lower than that of a commercially available MS-325 (KA = 3.0 × 104) RIME contrast agent. The low KA value of [Gd(DOTA-FPβGu)] is due to the pendant β-d-glucopyranuronic acid moiety. Therefore, [Gd(DOTA-FPβGu)] can be used for detection of β-glucuronidase through RIME modulation. The detail mechanism of enzymatic activation of [Gd(DOTA-FPβGu)] was elucidated by LC-MS. The kinetics of β-glucuronidase catalyzed hydrolysis of [Eu(DOTA-FPβGu)] at pH 7.4 best fit the Miechalis-Menten kinetic mode with Km = 1.38 mM, k cat = 3.76 × 103, and kcat/Km = 2.72 × 103 M-1 s-1. The low K m value indicates high affinity of β-glucuronidase for [Gd(DOTA-FPβGu)] at physiological pH. Relaxometric studies revealed that T1 relaxivity of [Gd(DOTA-FPβGu)] changes in response to the concentration of β-glucuronidase. Consistent with the relaxometric studies, [Gd(DOTA-FPβGu)] showed significant change in MR image signal in the presence of β-glucuronidase and HSA. In vitro and in vivo MR images demonstrated appreciable differences in signal enhancement in the cell lines and tumor xenografts in accordance to their expression levels of β-glucuronidase.