127770-45-0
Chemical Structure
5(6)-Carboxy-2',7'-dichlorofluorescein diacetate
- CAS No.: 127770-45-0
- Formula:C25H14Cl2O9
- Molecular Weight:529.28
IUPAC Name: 3',6'-diacetoxy-2',7'-dichloro-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid compound with 3',6'-diacetoxy-2',7'-dichloro-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-6-carboxylic acid (1:1)
InChIKey: LZMPJBOMBCYYMP-UHFFFAOYSA-N
SMILES: ClC1=C(OC(C)=O)C=C2OC3=CC(OC(C)=O)=C(Cl)C=C3C(OC4=O)(C5=CC=C(C(O)=O)C=C54)C2=C1.ClC6=C(OC(C)=O)C=C7OC8=CC(OC(C)=O)=C(Cl)C=C8C(OC9=O)(C%10=CC(C(O)=O)=CC=C%109)C7=C6
Biological Activity: 5 (6)-Carboxy-2',7'-dichlorofluorescein diacetate is a fluorescein-based reactive oxygen species (ROS) probe and also a MRP2 substrate. 5 (6)-Carboxy-2',7'-dichlorofluorescein diacetate serves as a substrate for intracellular esterases, which cleave its acetate groups to generate a fluorescent product capable of detecting intracellular ROS. 5 (6)-Carboxy-2',7'-dichlorofluorescein diacetate is ATP-dependent and is transported via a single MRP2 binding site; it competes with LTC4 for MRP2 binding sites and inhibits MRP2-mediated LTC4 transport (Ex/Em = 496/525 nm)[1][2][3][4].
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5(6)-Carboxy-2',7'-dichlorofluorescein diacetate | 97.5% | 5 (6)-Carboxy-2',7'-dichlorofluorescein diacetate is a fluorescein-based reactive oxygen species (ROS) probe and also a MRP2 substrate. 5 (6)-Carboxy-2',7'-dichlorofluorescein diacetate serves as a substrate for intracellular esterases, which cleave its acetate groups to generate a fluorescent product capable of detecting intracellular ROS. 5 (6)-Carboxy-2',7'-dichlorofluorescein diacetate is ATP-dependent and is transported via a single MRP2 binding site; it competes with LTC4 for MRP2 binding sites and inhibits MRP2-mediated LTC4 transport (Ex/Em = 496/525 nm). | ||||||||||||||||||||
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References
- [1]. Heredi-Szabo K, et al. Characterization of 5(6)-carboxy-2,'7'-dichlorofluorescein transport by MRP2 and utilization of this substrate as a fluorescent surrogate for LTC4. J Biomol Screen. 2008;13(4):295-301. [Content Brief]
- [2]. Pogue AI, et al. Metal-sulfate induced generation of ROS in human brain cells: detection using an isomeric mixture of 5- and 6-carboxy-2',7'-dichlorofluorescein diacetate (carboxy-DCFDA) as a cell permeant tracer. Int J Mol Sci. 2012;13(8):9615-9626. [Content Brief]
- [3]. Munić V, et al. Characterization of rhodamine-123, calcein and 5(6)-carboxy-2',7'-dichlorofluorescein (CDCF) export via MRP2 (ABCC2) in MES-SA and A549 cells. Eur J Pharm Sci. 2011;43(5):359-369. [Content Brief]
- [4]. Zamek-Gliszczynski MJ, et al. Pharmacokinetics of 5 (and 6)-carboxy-2',7'-dichlorofluorescein and its diacetate promoiety in the liver. J Pharmacol Exp Ther. 2003;304(2):801-809. [Content Brief]
