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

Abstract

Tagging of small bioactive molecules with a fluorophore is a highly sensitive method to trace their cellular activities through real-time visual information. Here we disclose a 7-nitrobenzo-2-oxa-1,3-diazole (NBD)-based, high-yielding, one-pot labeling protocol for hydroxylated molecules using Yamaguchi coupling as the key reaction. This methodology was successfully applied on several sensitive and complex hydroxylated bioactive compounds including 7-deacetylazadiradione, simvastatin, camptothecin, andrographolide, cinchonine, β-dihydroartemisinin, and azadirachtin A. Further, utility of this protocol was illustrated on the cytotoxic activity of azadiradione derivatives against several cancer cell lines through cell imaging of two qualified fluorescent probes.

• Authors: Saikat Haldar, Santosh Kumar, Swati P Kolet, Harshal S Patil, Dhiraj Kumar, Gopal C Kundu, Hirekodathakallu V Thulasiram
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 78 Issue 20 Pg. 10192-202 (Oct 18 2013) ISSN: 1520-6904 [Electronic] United States
• PMID: 24079457 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• 7-nitrobenzo-2-oxa-1,3-diazole
• Biological Products
• Fluorescent Dyes
• Limonins
• Nitrobenzenes
• Oxadiazoles
• azadirachtin

Topics

• Biological Products (chemistry)
• Fluorescent Dyes (chemistry)
• Hydrogen-Ion Concentration
• Limonins (chemistry, pharmacology)
• Nitrobenzenes (chemistry)
• Oxadiazoles (chemistry)
• Spectrometry, Fluorescence (methods)