One-pot fluorescent labeling protocol for complex hydroxylated bioactive natural products.
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.
Chemical Biology Unit, Division of Organic Chemistry, CSIR-National Chemical Laboratory , Pune-411008, India.
Saikat
S
Haldar
Santosh
S
Kumar
Swati P
SP
Kolet
Harshal S
HS
Patil
Dhiraj
D
Kumar
Gopal C
GC
Kundu
Hirekodathakallu V
HV
Thulasiram
D001688:Biological Products / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D036701:Limonins / Q000737:chemistry* / Q000494:pharmacology*; D009578:Nitrobenzenes / Q000737:chemistry*; D010069:Oxadiazoles / Q000737:chemistry*; D013050:Spectrometry, Fluorescence / Q000379:methods
C000588943:7-nitrobenzo-2-oxa-1,3-diazole; D001688:Biological Products; D005456:Fluorescent Dyes; D036701:Limonins; D009578:Nitrobenzenes; D010069:Oxadiazoles; C010329:azadirachtin