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Optical Photothermal Infrared-Fluorescence In Situ Hybridization (OPTIR-FISH)

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Published on: February 23, 2024

One-pot fluorescent labeling protocol for complex hydroxylated bioactive natural products.

Saikat Haldar¹, Santosh Kumar, Swati P Kolet

¹Chemical Biology Unit, Division of Organic Chemistry, CSIR-National Chemical Laboratory , Pune-411008, India.

The Journal of Organic Chemistry

|October 2, 2013

Summary

Researchers developed a new one-pot method to attach fluorescent tags to hydroxylated molecules, enabling real-time cellular tracking. This technique successfully labeled complex bioactive compounds for imaging cellular activities and drug efficacy.

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Area of Science:

Organic Chemistry
Chemical Biology
Bioorganic Chemistry

Background:

Tagging bioactive molecules with fluorophores allows sensitive, real-time cellular activity tracing.
Existing labeling methods may lack efficiency or applicability to complex molecules.

Purpose of the Study:

To develop a high-yielding, one-pot labeling protocol for hydroxylated molecules using a 7-nitrobenzo-2-oxa-1,3-diazole (NBD) tag.
To demonstrate the protocol's utility on diverse and sensitive bioactive compounds.

Main Methods:

Utilized Yamaguchi coupling as the key reaction for efficient labeling.
Applied a one-pot protocol for direct conjugation of NBD fluorophores to hydroxyl groups.
Successfully labeled complex molecules like simvastatin, camptothecin, and azadirachtin A.

Main Results:

Achieved high-yielding, one-pot labeling of various hydroxylated bioactive molecules.
Demonstrated successful application on sensitive and complex natural products and drugs.
Visualized the cytotoxic activity of azadiradione derivatives against cancer cell lines using the fluorescent probes.

Conclusions:

The developed NBD-based labeling protocol is efficient and versatile for hydroxylated compounds.
This method facilitates real-time cellular imaging and assessment of drug activity.
The protocol offers a valuable tool for chemical biology and drug discovery research.