Site-specific fluorescent labeling approaches for naringenin, an essential flavonone in plant nitrogen-fixation signaling pathways.
In search of an appropriate position for the fluorescent labeling, six chemically available positions of the flavonone core of naringenin have been examined. A number of azido-containing naringenin derivatives were accordingly prepared in various site-specific fashions, and the mild Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition successfully served as the common "Click" labeling tool in the final steps. On the basis of the biological activities of the first batch of labeled compounds, further optimization at the C-6 position of naringenin finally afforded naringenin-flu (27), which acquired 20% of the potency of naringenin and presented good optical properties. Entry of naringenin-flu into living Rhizobium cells was demonstrated by in vitro fluorescent imaging experiments.
Chen
Lei
L
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Li
Feng-Qing
FQ
Hou
Bi-He
BH
Hong
Guo-Fan
GF
Yao
Zhu-Jun
ZJ
D001386:Azides / Q000737:chemistry; D044950:Flavanones; D005419:Flavonoids; D005456:Fluorescent Dyes; D009586:Nitrogen Fixation; D012231:Rhizobium / Q000166:cytology / Q000378:metabolism; D015398:Signal Transduction
D001386:Azides; D044950:Flavanones; D005419:Flavonoids; D005456:Fluorescent Dyes; C005273:naringenin