BIOMAT Database Logo BIOMAT Database Logo

Fluorescent and biotinylated analogues of docetaxel: synthesis and biological evaluation. 1995

J Dubois, and M T Le Goff, and F Guéritte-Voegelein, and D Guénard, and Y Tollon, and M Wright
Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, Gif-sur-Yvette, France.

Six novel docetaxel analogues that possess a N-(7-nitrobenz-2-oxa-1,3-diazo-4-yl)amido-6-caproyl chain in position 7 or 3' (11 and 16a), a N-(7-nitrobenz-2-oxa-1,3-diazo-4-yl)amido-3-propanoyl group at 3' (16b) and a 5'-biotinyl amido-6-caproyl chain in position 7, 10 or 3', respectively, have been synthesized. These compounds exhibit activity against microtubule disassembly similar to that of docetaxel but show discrepant activities on living cells. Although addition of microtubules to 11, 16a and b enhance their fluorescence, no shift of the emission maxima was observed. The fluorescent docetaxel derivatives show a specific labeling of microtubules in living cells, demonstrating that the microtubule cytoskeleton constitutes their main subcellular localization.

UI MeSH Term Description Entries
D007614 Macropodidae A family of herbivorous leaping MAMMALS of Australia, New Guinea, and adjacent islands. Members include kangaroos, wallabies, quokkas, and wallaroos. Kangaroos,Macropus,Petrogale,Quokkas,Setonix,Wallabies,Wallabies, Rock,Wallaroo,Macropus robustus,Kangaroo,Petrogales,Quokka,Rock Wallabies,Rock Wallaby,Wallaby,Wallaby, Rock,Wallaroos
D008870 Microtubules Slender, cylindrical filaments found in the cytoskeleton of plant and animal cells. They are composed of the protein TUBULIN and are influenced by TUBULIN MODULATORS. Microtubule
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D001923 Brain Chemistry Changes in the amounts of various chemicals (neurotransmitters, receptors, enzymes, and other metabolites) specific to the area of the central nervous system contained within the head. These are monitored over time, during sensory stimulation, or under different disease states. Chemistry, Brain,Brain Chemistries,Chemistries, Brain
D002417 Cattle Domesticated bovine animals of the genus Bos, usually kept on a farm or ranch and used for the production of meat or dairy products or for heavy labor. Beef Cow,Bos grunniens,Bos indicus,Bos indicus Cattle,Bos taurus,Cow,Cow, Domestic,Dairy Cow,Holstein Cow,Indicine Cattle,Taurine Cattle,Taurus Cattle,Yak,Zebu,Beef Cows,Bos indicus Cattles,Cattle, Bos indicus,Cattle, Indicine,Cattle, Taurine,Cattle, Taurus,Cattles, Bos indicus,Cattles, Indicine,Cattles, Taurine,Cattles, Taurus,Cow, Beef,Cow, Dairy,Cow, Holstein,Cows,Dairy Cows,Domestic Cow,Domestic Cows,Indicine Cattles,Taurine Cattles,Taurus Cattles,Yaks,Zebus
D002478 Cells, Cultured Cells propagated in vitro in special media conducive to their growth. Cultured cells are used to study developmental, morphologic, metabolic, physiologic, and genetic processes, among others. Cultured Cells,Cell, Cultured,Cultured Cell
D005456 Fluorescent Dyes Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags. Flourescent Agent,Fluorescent Dye,Fluorescent Probe,Fluorescent Probes,Fluorochrome,Fluorochromes,Fluorogenic Substrates,Fluorescence Agents,Fluorescent Agents,Fluorogenic Substrate,Agents, Fluorescence,Agents, Fluorescent,Dyes, Fluorescent,Probes, Fluorescent,Substrates, Fluorogenic
D000077143 Docetaxel A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER. Docetaxel Anhydrous,Docetaxel Hydrate,Docetaxel Trihydrate,Docetaxol,N-Debenzoyl-N-tert-butoxycarbonyl-10-deacetyltaxol,NSC 628503,RP 56976,RP-56976,Taxoltere Metro,Taxotere,N Debenzoyl N tert butoxycarbonyl 10 deacetyltaxol,RP56976
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000972 Antineoplastic Agents, Phytogenic Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. Antineoplastics, Botanical,Antineoplastics, Phytogenic,Agents, Phytogenic Antineoplastic,Botanical Antineoplastics,Phytogenic Antineoplastic Agents,Phytogenic Antineoplastics

Related Publications

J Dubois, and M T Le Goff, and F Guéritte-Voegelein, and D Guénard, and Y Tollon, and M Wright
Synthesis and Biological Evaluation of Fluorescent Bryostatin Analogues.
April 2018, Chembiochem : a European journal of chemical biology,
J Dubois, and M T Le Goff, and F Guéritte-Voegelein, and D Guénard, and Y Tollon, and M Wright
Design, synthesis and biological evaluation of novel fluorinated docetaxel analogues.
February 2009, European journal of medicinal chemistry,
J Dubois, and M T Le Goff, and F Guéritte-Voegelein, and D Guénard, and Y Tollon, and M Wright
Biotinylated and fluorescent analogues of bradykinin.
August 1997, Biochemical Society transactions,
J Dubois, and M T Le Goff, and F Guéritte-Voegelein, and D Guénard, and Y Tollon, and M Wright
Deletion of the oxetane ring in docetaxel analogues: synthesis and biological evaluation.
December 2003, Organic letters,
J Dubois, and M T Le Goff, and F Guéritte-Voegelein, and D Guénard, and Y Tollon, and M Wright
Synthesis and biological evaluation of novel 3'-N-tert-butylsulfonyl analogues of docetaxel.
September 2008, Bioorganic & medicinal chemistry letters,
J Dubois, and M T Le Goff, and F Guéritte-Voegelein, and D Guénard, and Y Tollon, and M Wright
Synthesis and biological evaluation of biotinylated ZJ-101.
July 2023, Bioorganic & medicinal chemistry letters,
J Dubois, and M T Le Goff, and F Guéritte-Voegelein, and D Guénard, and Y Tollon, and M Wright
Synthesis and biological evaluation of (-)-laulimalide analogues.
February 2004, Bioorganic & medicinal chemistry letters,
J Dubois, and M T Le Goff, and F Guéritte-Voegelein, and D Guénard, and Y Tollon, and M Wright
Synthesis and biological evaluation of helioxanthin analogues.
April 2013, Bioorganic & medicinal chemistry,
J Dubois, and M T Le Goff, and F Guéritte-Voegelein, and D Guénard, and Y Tollon, and M Wright
Synthesis and biological evaluation of gambierol analogues.
August 2003, Bioorganic & medicinal chemistry letters,
J Dubois, and M T Le Goff, and F Guéritte-Voegelein, and D Guénard, and Y Tollon, and M Wright
Synthesis and biological evaluation of (-)-laulimalide analogues.
September 2003, Organic letters,
Copied contents to your clipboard!