105454-04-4Relevant articles and documents
Facile Synthesis of 7-epi-Taxane and Its Derivatives and Preliminary Evaluation of Anticancer Activity
Li, Zhao,Feng, Jia,Zou, Kun,Yang, Zhuo,Zhang, Yong,Xu, Zhijian,Li, Bo,Shi, Jiye,Li, Yiming,Zhu, Weiliang,Chen, Kaixian
, p. 1165 - 1176 (2016)
7-epi-Taxane has been achieved efficiently in gram scale from natural taxane via inversion of the 7-hydroxyl group simply using Ag2O as catalyst and DMF as solvent. The catalyst could be quantitatively recovered by filtration without loss of catalytic activity. This condition is also applicable to the direct epimerization of taxane derivatives (e.g., docetaxel and paclitaxel) to 7-epi-taxane derivatives (e.g., 7-epi-docetaxel and 7-epi-paclitaxel). Furthermore, 33 ester derivatives of 7-epi-taxane with different amino acid moieties at the position of C-13 were successfully synthesized via esterification without protecting C-7-OH. Bioassay results revealed that compounds 13 and 18 have good selectivity against prostatic cancer cell line DU145, with IC50value as low as 15.9 nmol/L for 18.
Paclitaxel stability in solution
MacEachern-Keith,Butterfield, L. J. Wagner,Mattina, M. J. Incorvia
, p. 72 - 77 (1997)
Research in this laboratory has focused on the cytokinetic effect of taxanes on nonmammalian systems. Taxanes are a class of natural products that includes the well-known anticancer compound, paclitaxel (Taxol). Our methodology for the study of fungal growth in liquid medium amended with paclitaxel included membrane solid phase extraction (SPE) of the fungal broth. This was followed by elution of paclitaxel from the SPE membrane using methanol. The methanolic solution was evaporated under relatively mild conditions, namely 41-43°C and approximately 85 kPag. Analysis of the concentrated solution indicated that it contained a considerable quantity of 7-epi-taxol and smaller quantities of 7-epi-10-deacetyltaxol, 10-deacetyltaxol, and baccatin III, in addition to paclitaxel, even in those cases where the medium had not been inoculated with fungus. Obviously, fungal metabolism could not account for these observations. Although epimerization in solution at carbon 7 in the C ring of the taxane core has been observed and reported previously, no detailed study of the solution kinetics of paclitaxel degradation, including epimerization, is available. We report here our investigation of the stability of paclitaxel in several solvent systems at various temperatures and pressures. The investigations indicate that the apparent activation energy barrier (Ea) for paclitaxel degradation is highly dependent on experimental conditions. These stability studies emphasize the need to demonstrate explicitly that all taxane degradation, including epimerization, observed during in vitro studies is not an artifact of the analytical methodology employed.
Method of generating 7-epipaclitaxel by converting hydrocarbonate into taxol
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Paragraph 0019-0047, (2019/07/04)
The invention relates to a method of generating 7-epipaclitaxel by converting hydrocarbonate into taxol. The method comprises the steps of dissolving hydrocarbonate in sterile water, adding the same volume of the sterile water into an acetonitrile solutio
Biological degradation of taxol by action of cultured cells on 7-acetyltaxol-2″-yl glucoside
Shimoda, Kei,Mikuni, Katsuhiko,Nakajima, Kiyoshi,Hamada, Hatsuyuki,Hamada, Hiroki
, p. 362 - 363 (2008/09/20)
Biodegradation pathways of taxol in cultured cells of Synechocystis sp. PCC 6803, Synechococcus sp. PCC 7942, Marchantia polymorpha, Nicotiana tabacum, and Glycine max were investigated using a water-soluble taxol derivative, 7-ace-tyltaxol-2″-yl glucoside, as the substrate. Although cyanobacteria, Synechocystis sp. PCC 6803 and Synechococcus sp. PCC 7942, and a lower plant, M. polymorpha, catalyzed the epimerization at 7-position of taxol skeleton, no epimerization occurred with higher plants, N. tabacum and G. max. On the other hand, Synechocystis sp. PCC 6803, Synechococcus sp. PCC 7942, M. polymorpha, and N. tabacum catalyzed hydrolysis at 13-position of taxol to give baccatin III and 10-deacetyl baccatin III. Both cyanobacteria cells also deacetylated 7-epi-baccatin III at its 10-position. M. polymorpha and G. max deacetylated at 10-position of taxol. Copyright