Synthesis and microtubule binding of fluorescent paclitaxel derivatives.
The preparation of two new fluorescent derivatives of paclitaxel in which the fluorophore is bonded to paclitaxel at the C-10 position is reported. Both analogues, 10-deacetyl-10-(m-aminobenzoyl)paclitaxel (1, BTax) and 10-deacetyl-10-[7-(diethylamino) coumarin-3-carbonyl]paclitaxel (2, CTax) retain good activity as promoters of in vitro tubulin assembly. Microtubule binding enhances the emission intensity of both probes.
Baloglu
E
E
Department of Chemistry, M/C 0212, Virginia Polytechnic Institute and State University, Blacksburg, VA 24061, USA.
Kingston
D G
DG
Patel
P
P
Chatterjee
S K
SK
Bane
S L
SL
D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D008870:Microtubules / Q000378:metabolism*; D017239:Paclitaxel / Q000031:analogs & derivatives / Q000737:chemistry* / Q000378:metabolism; D013050:Spectrometry, Fluorescence; D013329:Structure-Activity Relationship; D043823:Taxoids; D014404:Tubulin / Q000378:metabolism
C442365:10-deacetyl-10-(3-aminobenzoyl)paclitaxel; C442366:10-deacetyl-10-(7-(diethylamino)coumarin-3-carbonyl)paclitaxel; D005456:Fluorescent Dyes; D043823:Taxoids; D014404:Tubulin; D017239:Paclitaxel