5-Carboxyfluorescein diacetate

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5-Carboxyfluorescein diacetate

5-Carboxyfluorescein diacetate | 79955-27-4

Catalog Number F04-0034
Category Fluorescein FAM
Molecular Formula C25H16O9
Molecular Weight 460.394
Catalog Number Size Price Quantity
F04-0034 500 mg $228

Product Introduction

5-Carboxyfluorescein diacetate is a non-fluorescent, cell-permeant hydrophobic probe that is used in the synthesis of rhodamines.

Chemical Information

Synonyms 5-CFDA
Purity >93.0%(T)(HPLC)
IUPAC Name 3',6'-diacetyloxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid
Canonical SMILES CC(=O)OC1=CC2=C(C=C1)C3(C4=C(C=C(C=C4)C(=O)O)C(=O)O3)C5=C(O2)C=C(C=C5)OC(=O)C
InChI InChI=1S/C25H16O9/c1-12(26)31-15-4-7-19-21(10-15)33-22-11-16(32-13(2)27)5-8-20(22)25(19)18-6-3-14(23(28)29)9-17(18)24(30)34-25/h3-11H,1-2H3,(H,28,29)
InChI Key WPUZGNPQMIWOHE-UHFFFAOYSA-N
Appearance Solid
MDL Number MFCD00036872
  • Product Specification
  • Application
Condition To Avoid Heat Sensitive
Storage <0 °C
GHS Hazard Statements Not Classified Reported as not meeting GHS hazard criteria by 38 of 39 companies (only ~ 2.6% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

5-Carboxyfluorescein diacetate (CFDA) stands out as a fluorescent dye with widespread use in diverse biological applications, thanks to its unique capability to penetrate cells and emit fluorescence upon enzymatic conversion. Here are four key applications of 5-Carboxyfluorescein diacetate:

Cell Viability Assays: CFDA plays a pivotal role in cell viability assays by assessing the viability of cells within a population. Once inside the cell, esterases transform CFDA into carboxyfluorescein, a highly fluorescent compound that accumulates in viable cells. This method enables researchers to efficiently differentiate between live and dead cells, aiding in toxicology studies and drug screening by providing crucial insights into cellular health and responses.

Flow Cytometry: Widely employed in flow cytometry, CFDA facilitates the study of cell populations and monitoring of cell proliferation dynamics. Cells labeled with CFDA emit fluorescence that can be quantitatively measured using flow cytometers, offering detailed information on cell cycle status and division rates. This application is particularly valuable in immunology research and cancer cell analysis, shedding light on cellular behaviors and interactions with precision and depth.

Tracking Cell Migration: CFDA emerges as a valuable tool for labeling and tracing cell migration patterns in various biological studies. Once labeled, cells retain their fluorescence, allowing for real-time visualization and tracking of their movements over time using fluorescence microscopy. This technique is pivotal for unraveling complex processes such as tissue regeneration, immune cell trafficking, and cancer metastasis, providing insights into the dynamics and mechanisms governing cell movements in diverse biological contexts.

Intracellular pH Measurement: Leveraging its pH-sensitive fluorescence properties, CFDA serves as a reliable option for measuring intracellular pH in living cells. Changes in fluorescence intensity of CFDA-loaded cells correspond to fluctuations in intracellular pH, offering valuable insights into cellular metabolic states and responses to environmental cues. This application is critical for advancing research in cell physiology and pathophysiology, enabling scientists to unravel the intricacies of cellular processes and adaptations to varying conditions with precision and depth.

Computed Properties

XLogP3 3.2
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 9
Rotatable Bond Count 5
Exact Mass 460.07943208 g/mol
Monoisotopic Mass 460.07943208 g/mol
Topological Polar Surface Area 125Ų
Heavy Atom Count 34
Formal Charge 0
Complexity 828
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes

Literatures

PMIDPublication DateTitleJournal
22541068 2012-05-24 Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions Journal of medicinal chemistry
22558349 2012-01-01 Regulation of epithelial cell morphology and functions approaching to more in vivo-like by modifying polyethylene glycol on polysulfone membranes PloS one
22027652 2011-12-01 Functional defect caused by the 4544G>A SNP in ABCC2: potential impact for drug cellular disposition Pharmacogenetics and genomics
21609321 2011-08-01 Function of MRP1/ABCC1 is not dependent on cholesterol or cholesterol-stabilized lipid rafts The Biochemical journal
20880209 2011-01-01 Development of a nondestructive fluorescence-based enzymatic staining of microcolonies for enumerating bacterial contamination in filterable products Journal of applied microbiology

Patents

Publication NumberTitlePriority Date
KR-20220158291-A A pharmaceutical composition containing cell-transducing Inorganic Pyrophosphatase 1 fusion protein for preventing or treating motor neuronal disorder 2021-05-20
KR-20220147167-A Pharmaceutical composition for treating cerebral ischemia containing cell-transducing PGAM5 fusion protein 2021-04-26
KR-20220142557-A Pharmaceutical composition for treating cerebral ischemia containing cell-transducing CRYM fusion protein 2021-04-14
JP-2022037654-A Compounds localized in the Golgi apparatus and their use 2020-08-25
JP-2021138671-A PPM1D inhibitor 2020-03-09
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