233759-98-3

Usage

Uses

Used in Research and Diagnostic Applications:
FLUORESCEIN-O'-ACETIC ACID is used as a fluorescent label for research and diagnostic purposes. Its ability to react with amines and form isomerically homogeneous derivatives allows for the detection and analysis of specific molecules or biological processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, FLUORESCEIN-O'-ACETIC ACID is used as a fluorescent label to track the distribution and metabolism of drugs within the body. This helps researchers understand the pharmacokinetics and pharmacodynamics of new drug candidates, ultimately contributing to the development of more effective and safer medications.
Used in Environmental Science:
FLUORESCEIN-O'-ACETIC ACID is also utilized in environmental science as a fluorescent label to study the behavior of pollutants and contaminants in the environment. By tracking the movement and interaction of these substances with living organisms, researchers can better understand their impact on ecosystems and develop strategies for mitigation and remediation.
Used in Biotechnology:
In the field of biotechnology, FLUORESCEIN-O'-ACETIC ACID is employed as a fluorescent label to study protein-protein interactions, enzyme activity, and cellular processes. This information is crucial for the development of new biotechnological applications, such as the creation of genetically modified organisms or the design of novel biosensors.
Used in Medical Diagnostics:
FLUORESCEIN-O'-ACETIC ACID is used as a fluorescent label in medical diagnostics to detect and monitor various diseases. Its ability to bind to specific molecules or cells allows for the visualization of disease biomarkers, which can aid in early detection and more accurate diagnosis of conditions such as cancer, autoimmune disorders, and infectious diseases.

InChI:InChI=1/C22H14O7/c23-12-5-7-16-18(9-12)29-19-10-13(28-11-20(24)25)6-8-17(19)21(16)14-3-1-2-4-15(14)22(26)27/h1-10H,11H2,(H,24,25)(H,26,27)

Upstream product

• 824424-13-7 tert-butyl 2-((3′-hydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthen]-6′-yl)oxy)acetate 
• 2321-07-5 fluorescein 

Relevant academic research and scientific papers

Ratiometric Fluorescence Monitoring of Antibody-Guided Drug Delivery to Cancer Cells

Ratiometric measurements utilizing two independent fluorescence signals from a dual-dye molecular system help to improve the detection sensitivity and quantification of many analytical, bioanalytical, and pharmaceutical assays, including drug delivery monitoring. Nevertheless, these dual-dye conjugates have never been utilized for ratiometric monitoring of antibody (Ab)-guided targeted drug delivery (TDD). Here, we report for the first time on the new, dual-dye TDD system, Cy5s-Ab-Flu-Aza, comprising the switchable fluorescein-based dye (Flu) linked to the anticancer drug azatoxin (Aza), reference pentamethine cyanine dye (Cy5s), and Her2-specific humanized monoclonal Trastuzumab (Herceptin) antibody. The ability of ratiometric fluorescence monitoring of drug release was demonstrated with this model system in vitro in the example of the human breast cancer SKBR3 cell line overexpressing Her2 receptors. The proposed approach for designing ratiometric, antibody-guided TDD systems, where a drug-switchable dye conjugate and a reference dye are independently linked to an antibody, can be expanded to other drugs, dyes, and antibodies. Replacement of the green-emitting dye Flu, which was found not detectable in vivo, with a longer-wavelength (red or near-IR) switchable fluorophore should enable quantification of drug release in the body.

Isonitrile-responsive and bioorthogonally removable tetrazine protecting groups

In vivo compatible reactions have a broad range of possible applications in chemical biology and the pharmaceutical sciences. Here we report tetrazines that can be removed by exposure to isonitriles under very mild conditions. Tetrazylmethyl derivatives are easily accessible protecting groups for amines and phenols. The isonitrile-induced removal is rapid and near-quantitative. Intriguingly, the deprotection is especially effective with (trimethylsilyl)methyl isocyanide, and serum albumin can catalyze the elimination under physiological conditions. NMR and computational studies revealed that an imine-tautomerization step is often rate limiting, and the unexpected cleavage of the Si-C bond accelerates this step in the case with (trimethylsilyl)methyl isocyanide. Tetrazylmethyl-removal is compatible with use on biomacromolecules, in cellular environments, and in living organisms as demonstrated by cytotoxicity experiments and fluorophore-release studies on proteins and in zebrafish embryos. By combining tetrazylmethyl derivatives with previously reported tetrazine-responsive 3-isocyanopropyl groups, it was possible to liberate two fluorophores in vertebrates from a single bioorthogonal reaction. This chemistry will open new opportunities towards applications involving multiplexed release schemes and is a valuable asset to the growing toolbox of bioorthogonal dissociative reactions.