6-Carboxyfluorescein diacetate

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6-Carboxyfluorescein diacetate

6-Carboxyfluorescein diacetate | 3348-03-6

Catalog Number A16-0067
Category Cell proliferation tracer Fluorescent Probes
Molecular Formula C25H16O9
Molecular Weight 460.39
Catalog Number Size Price Quantity
A16-0067 -- $--

Product Introduction

6-Carboxyfluorescein diacetate is a membrane-permeant prodrug of 6-Carboxyfluorescein, which has been used to differentiate viable cells from apoptotic cells.

Chemical Information

Synonyms 6-CFDA; 3',6'-Diacetoxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-6-carboxylic acid
IUPAC Name 3',6'-diacetyloxy-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-carboxylic acid
Canonical SMILES CC(=O)OC1=CC2=C(C=C1)C3(C4=C(O2)C=C(C=C4)OC(=O)C)C5=C(C=CC(=C5)C(=O)O)C(=O)O3
InChI InChI=1S/C25H16O9/c1-12(26)31-15-4-7-18-21(10-15)33-22-11-16(32-13(2)27)5-8-19(22)25(18)20-9-14(23(28)29)3-6-17(20)24(30)34-25/h3-11H,1-2H3,(H,28,29)
InChI Key QMOGCCYGOPYYNT-UHFFFAOYSA-N
  • Product Specification
  • Application
Excitation 553
Emission 575
Signal Warning
GHS Hazard Statements H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
Precautionary Statement Codes P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (The corresponding statement to each P-code can be found at the GHS Classification page.)

6-Carboxyfluorescein diacetate (CFDA) is a versatile fluorescent dye widely utilized in diverse biological and biochemical settings. Here we explore four key applications of CFDA:

Cell Viability Assays: CFDA serves as a cornerstone for evaluating cell viability and cytotoxicity across various cell types. Upon cellular uptake, CFDA undergoes hydrolysis by intracellular esterases, unveiling the fluorescent derivative 6-carboxyfluorescein. This fluorescence can be quantified, offering researchers a window into the realm of viable cells within a population.

Flow Cytometry: Delving into the realms of cell tracking and proliferation studies, 6-Carboxyfluorescein diacetate finds extensive application in flow cytometry. Following its conversion to a fluorescent entity within cells, it becomes a beacon for traversing through multiple cell divisions. By tracking the dilution of fluorescence intensity, scientists can gain insights into cell proliferation rates and lineage tracing dynamics.

Intracellular pH Measurement: A realm where CFDA truly shines is in the measurement of intracellular pH levels. Its fluorescence intensity is intricately linked with pH variations, offering researchers a tool for real-time monitoring within cells. By introducing CFDA into cellular landscapes, it undergoes hydrolysis to release the pH-sensitive dye 6-carboxyfluorescein, unveiling a dynamic palette for exploring intracellular pH fluctuations across diverse experimental terrains.

Confocal Microscopy: Entering the realm of confocal microscopy, CFDA emerges as a vital ally for imaging live cells and tissues with finesse. Its exceptional fluorescence properties, coupled with non-toxicity and cell membrane penetration capabilities, make it a prized asset for live-cell imaging endeavors. By harnessing CFDA, researchers can peer into the intricate world of cellular processes such as endocytosis, organelle dynamics, and cellular motility, painting a vivid picture with high spatial resolution.

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
22727158 2012-07-01 Effect of Pru p 3 on dendritic cell maturation and T-lymphocyte proliferation in peach allergic patients Annals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology
21841816 2011-11-01 Chimeric flagellin expressed by Salmonella typhimurium induces an ESAT-6-specific Th1-type immune response and CTL effects following intranasal immunization Cellular & molecular immunology
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
20796276 2010-08-26 The PI3K/Akt pathway upregulates Id1 and integrin α4 to enhance recruitment of human ovarian cancer endothelial progenitor cells BMC cancer
19756838 2010-03-01 Apoptosis- and necrosis-induced changes in light attenuation measured by optical coherence tomography Lasers in medical science

Patents

Publication NumberTitlePriority Date
JP-7190534-B1 Microorganism detection method 2021-06-14
WO-2022264454-A1 Method for detecting microorganisms 2021-06-14
WO-2022165332-A2 Functionalized 1,3-benzene diols and their method of use for the treatment of inflammation and pain 2021-02-01
WO-2022126416-A1 Anti-bcma antibody, preparation method therefor and application thereof 2020-12-16
WO-2022116591-A1 Pluripotent stem cell and derivative thereof 2020-12-04
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