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2',7'-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester

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Name

2',7'-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester

EINECS N/A
CAS No. 117464-70-7 Density 1.2837 (rough estimate)
PSA 264.39000 LogP 3.72360
Solubility N/A Melting Point N/A
Formula C40H36 O19 Boiling Point 692.41°C (rough estimate)
Molecular Weight 880.75 Flash Point 85 °C
Transport Information N/A Appearance N/A
Safety
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 22-26-36
Risk Codes 36/37/38
Molecular Structure Molecular Structure of 117464-70-7 (BCECF-AM) Hazard Symbols
Synonyms

Spiro[isobenzofuran-1(3H),9'-[9H]xanthene]-2',7'-dipropanoicacid, 3',6'-bis(acetyloxy)-5(or 6)-[[(acetyloxy)methoxy]carbonyl]-3-oxo-,bis[(acetyloxy)methyl] ester (9CI); BCECF-AM

 

2',7'-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester Chemical Properties

Molecular Structure:

Molecular Formula: C42H40O21
Molecular Weight: 880.75 
Product Name: 2',7'-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester
Synonyms of 2',7'-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester (CAS NO.117464-70-7): 2',7'-Ccae ; Bcecf-AM ; Bis(carboxyethyl)carboxyfluorescein acetoxymethyl ester ; Spiro(isobenzofuran-1(3H),6'-(2H,6H)pyrano(3,2-b)xanthene)-8'-propanoic acid, 9'-(acetyloxy)-ar-(((acetyloxy)methoxy)carbonyl)-3',4'-dihydro-2',3-dioxo-, (acetyloxy)methyl ester
CAS NO: 117464-70-7

2',7'-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester Safety Profile

Hazard Codes of 2',7'-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester (CAS NO.117464-70-7): IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-26-36 
S22: Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.

2',7'-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester Specification

   2',7'-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein (BCECF) is a fluorescent probe used to examine multidrug resistance-associated protein (MRP) transporter activity in cells. BCECF is introduced into the cell as the nonfluorescent membrane permeable acetoxymethyl ester, BCECF-AM, where it is hydrolyzed to the membrane impermeable BCECF. The lipophilic nature of BCECF-AM suggests it may be a substrate for other drug efflux transporters such as P-glycoprotein (P-gp) and the breast cancer resistance protein (BCRP). To assess the drug efflux transporter interactions of of 2',7'-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester (CAS NO.117464-70-7) (BCECF-AM) and BCECF, accumulation studies were examined in various drug efflux-expressing cells. Inhibition of P-gp, BCRP, and/or MRP produced distinct changes in the time-dependent accumulation of BCECF in the cells. Treatment with GF120918 produced an immediate and sustained effect throughout the entire time course examined. Fumitremorgin C only affected BCECF accumulation at the early time points, whereas the impact of indomethacin on BCECF accumulation was observed only at the latter time points. Permeability studies in bovine brain microvessel endothelial cells indicated an increased basolateral-to-apical transport of BCECF, which could be reduced in the presence of either indomethacin or GF120918. These results indicate that the intracellular accumulation and transcellular permeability of BCECF are sensitive to a variety of drug efflux interactionsThese results likely reflect an interaction of the ester form with P-gp and BCRP during the initial accumulation process, and an interaction of the free acid form with MRP after hydrolysis in the cell. Copyright 2004 Wiley-Liss, Inc. and the American Pharmacists Association.

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