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Antitubulin Agents
Published in David E. Thurston, Ilona Pysz, Chemistry and Pharmacology of Anticancer Drugs, 2021
Other production methods have been investigated, and scientists from the Institute for Bioprocessing and Analytical Measurement Techniques in Germany have recently shown that a genetically modified strain of Escherichia coli can be used to convert 10-deacetylbaccatin III (obtained from the leaves of Taxus brevifolia), to baccatin II, a precursor of paclitaxel. This procedure has the potential to produce paclitaxel in a cost-effective manner. In a further development, paclitaxel has been shown to be produced by a newly described fungus resident in yew trees. Paclitaxel has also been found in a number of other endophytic fungi, thus pointing to the possibility of production through culturing one of these fungal species. Finally, taxane-type molecules including 10-deacetylbaccatin III, baccatin III, paclitaxel, paclitaxel C, and 7-epi-paclitaxel have been found in the shells and leaves of hazel plants. These are waste products produced in large amounts by a number of food industries, and so could provide another economic source of drugs of this type.
On Biocatalysis as Resourceful Methodology for Complex Syntheses: Selective Catalysis, Cascades and Biosynthesis
Published in Peter Grunwald, Pharmaceutical Biocatalysis, 2019
Andreas Sebastian Klein, Thomas Classen, Jörg Pietruszka
The small biosynthetic amounts of anti-cancer agent paclitaxel (25, taxol) obtained from the Pacific yew (Taxus brevifolia) led to the development of alternative production strategies (Patel, 1998). Although total syntheses were published, these were not economically justifiable due to the complexity of the molecule. Since an intermediate of the taxol biosynthesis, 10-deacetylbaccatin III (28), occurs in larger amounts in the leaves of the European yew (Taxus baccata), Holton (1993) developed a semisynthesis approach for the production of taxol (25). Starting from 10-deacetylbaccatin III (28), the 7-O-triethylsilyl baccatin III (29) is first obtained by two consecutive protection reactions, which resulted after conversion with the Ojima lactone (30) and a subsequent deprotection in taxol (Fig. 21.11).
Strategies for the drug discovery and development of taxane anticancer therapeutics
Published in Expert Opinion on Drug Discovery, 2022
Changwei Wang, Angelo Aguilar, Iwao Ojima
In the 1980s, the only known source of paclitaxel was from the bark of Pacific yew (taxus brevifolia) [7] and persistent over-harvesting of this slow growing tree once resulted in serious environmental issues [7]. Fortunately, this problem was resolved by the development of practical semi-synthesis of paclitaxel from 10-deacetylbaccatin III (10-DAB III), which is much more abundant in the needles of European yew (Taxus baccata), up to ~1 g kg−1 of fresh biomass, and these yew needles are renewable. Thus, abundantly culturable European yew secured the production of paclitaxel and docetaxel [5,7], which allowed INDENA SpA, Italy, to supply 10-DAB III to most of the global market [7]. Now, the ‘South No. 1 Yew,’ an elite clone from Taxus wallichiana Zucc var mairei, the fastest growing species of Taxus spp. that is endemic to China, is widely cultivated in Fujian and Yunnan provinces of China to produce 10-DAB III (0.9–1% of dry biomass) at much cheaper cost [8].
Cancer prevention and treatment using combination therapy with natural compounds
Published in Expert Review of Clinical Pharmacology, 2020
Paclitaxel is a taxane. It was isolated from the bark of the Pacific yew tree in 1967 through organic solvent extraction, concentration and final purification of the isolate by chromatography. It was found to have anticancer properties. Yields of the compound through extraction from the tree bark were inconsistent and the extraction killed the tree in the process [158]. A semisynthetic approach was developed in 1994. The current pharmaceutical preparation begins with 10-deacetylbaccatin III, an advanced paclitaxel precursor available in high yields from the more abundant European yew. It is used to treat a wide variety of malignancies [159].
PEGylated solid lipid nanoparticles functionalized by aptamer for targeted delivery of docetaxel in mice bearing C26 tumor
Published in Drug Development and Industrial Pharmacy, 2022
Zahra Shakib, Asma Mahmoudi, Seyedeh Alia Moosavian, Bizhan Malaekeh-Nikouei
Docetaxel (DTX) is a lipophilic anticancer drug from the taxoid family [6] and can be prepared by semi-synthesization of 10-deacetylbaccatin III, derived from the needles and bark of the Pacific yew tree [7,8]. DTX stops the cell division cycle between the prophase and anaphase stages and leads to the apoptosis of cancer cells. It is more potent than paclitaxel [9,10]. DTX is used in the treatment of colorectal cancer, ovarian cancer, breast cancer, non-small cell lung cancer and other tumors [6,11].