Practical Semisynthesis and Antimitotic Activity of Docetaxel and Side-Chain Analogues

Commerçon, Alain; Bourzat, Jean‐Dominique; Didier, E.; Lavelle, François

doi:10.1021/bk-1995-0583.ch017

Cited by 23 publications

(24 citation statements)

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“…Some researchers found that T. baccata (European Yew), T. caspidata and hybrids species such as T. x media Hicksii produce Taxol precursors [5,7]. These precursor are used for chemical synthesis of Taxol and can be converted to an analog of taxol in the laboratory [17].…”

Section: Alternative Speciesmentioning

confidence: 99%

“…Leaves and twigs are a source of 10-deacetylbaccatin III (10-DAB), although yield much lower but they are more renewable resource [5,30]. Docetaxel [Taxotere] is partially-synthetic derivative of Taxol and results from the modification of paclitaxel's side chain.…”

Section: Semi-synthetic Taxolmentioning

confidence: 99%

“…It acts to kill cancer cells in the same way as Paclitaxel and has potent cytotoxic activity. It is practical and useful in the treatment of prostate cancer, breast, ovarian and lung cancer [5].…”

Section: Semi-synthetic Taxolmentioning

confidence: 99%

“…Investigations for isolation and extraction Taxol or its precursors from leaves and stems of other Taxus species, including T. baccata and T. caspidata and hybrids species (e.g. T. x media Hicksii) has been done [5,7]. This method seems to be suitable for the production, but purification and isolation of the natural precursor for the synthesis of Taxol, due to the present waxes, chlorophyll, phenolic compounds, lipids and other interfering plant compounds is very complicated [5,6].…”

Section: Semi-synthetic Taxolmentioning

confidence: 99%

“…Semi-synthesis of taxol is dependent on natural compounds such Bacatin III. The leaves and stems are more considerable as a renewable resource for precursors [5,6].…”

Section: Introductionmentioning

confidence: 99%

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New Approach To Improve Taxol Biosynthetic

Badi¹,

Abdoosi²,

Farzin³

2015

TJS

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Taxol (Generic name for paclitaxel) is a complicated diterpene compound that is initially isolated from yew plants. Taxol is one of the most exciting natural ingredients to treat various cancers, including breast cancer, ovarian carcinoma, melanoma, and lung cancer. Limited number of yew trees, low content of taxol in plant tissue, slow growing and killing the tree to bark harvesting are significant restrictions that have led to the supply and availability of this important substance faced with challenges. Many attempts to complete synthesis, semi-synthesis, finding new source e.g alternative spices, other plant, microorganisms and establishment of the cell suspension cultures have been carried out. Cell culture is an appropriate strategy for stable production by using a small part of the plant as explants. Elicitors such as methyl jasmonate family compounds are powerfull stimulator for production of taxol. Methyl jasmonate increases the amount of taxol by enhancing the expression levels of taxol biosynthesis enzymes such as Geranyl-geranyl pyrophosphate synthase (GGPPs) and taxadienesynthesis (TDS). New approach including genetic and metabolic engineering can be led to increasing the taxol production by the over-expression of genes controlling limiting steps or by suppressing the undesired taxanes by employing antisense technology. The yew-coding genes associated with the production of taxol have been cloned. However, genetic manipulation strategies are not yet complete. This paper reviews the various ways to improve Taxol production.

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Section: Alternative Speciesmentioning

confidence: 99%

Section: Semi-synthetic Taxolmentioning

confidence: 99%

Section: Semi-synthetic Taxolmentioning

confidence: 99%

Section: Semi-synthetic Taxolmentioning

confidence: 99%

“…Semi-synthesis of taxol is dependent on natural compounds such Bacatin III. The leaves and stems are more considerable as a renewable resource for precursors [5,6].…”

Section: Introductionmentioning

confidence: 99%

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New Approach To Improve Taxol Biosynthetic

Badi¹,

Abdoosi²,

Farzin³

2015

TJS

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The Chemical Synthesis of C‐Ring Aryl Taxoids

Nicolaou

Claiborne

Paulvannan

et al. 1997

Chemistry A European J

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Abstract:We designed and targeted for synthesis the C-ring aryl taxoids 2a-c in order to develop methods for the construction of the taxoid skeleton and to test their cytotoxicity against tumor cells. Compound 2 a was synthesized by a convergent route from hydrazone 5 and aldehyde 4. Key steps included a Shapiro reaction to join 5 and 4, a McMurry coupling to construct the %membered ring, a carbonate opening to introduce the 2-ben- Keywordsantitumor agents -carbocyclesdrug research taxol zoate group, and an allylic oxidation followed by side-chain attachment. A similar sequence led to compound 2c, whereas attempts to attain 2 b were thwarted by the lability of the benzyl group during the carbonate opening. The biological activity of 2a and 2 c against tumor cells was considerably less than that of taxol.

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Paclitaxel production using co-culture of Taxus suspension cells and paclitaxel-producing endophytic fungi in a co-bioreactor

Tao

2009

Appl Microbiol Biotechnol

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The co-culture of the suspension cells of Taxus chinensis var. mairei and its endophytic fungi, Fusarium mairei, in a 20-L co-bioreactor was successfully established for paclitaxel production. The co-bioreactor consists of two-unit tanks (10 L each) with a repairable separate membrane in the center, culturing Taxus suspension cells in one tank and growing fungi in another. By optimizing the co-culture conditions, there was a desirable yield of paclitaxel in Taxus cell cultures. The Taxus cell cultures by co-culture produced 25.63 mg/L of paclitaxel within 15 days; it was equivalent to a productivity of 1.71 mg/L per day and 38-fold higher than that by uncoupled culture (0.68 mg/L within 15 days). The optimum conditions for co-culture in the co-bioreactor were: B5 medium, inoculating fungi when Taxus cells had grown for 5 days in the co-bioreactor, hydrophilic separate membrane in the center of the co-bioreactor, and air flow rate of 1:0.85 v/v/m in fungus cultures.

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Practical Semisynthesis and Antimitotic Activity of Docetaxel and Side-Chain Analogues

Cited by 23 publications

References 0 publications

New Approach To Improve Taxol Biosynthetic

New Approach To Improve Taxol Biosynthetic

The Chemical Synthesis of C‐Ring Aryl Taxoids

Paclitaxel production using co-culture of Taxus suspension cells and paclitaxel-producing endophytic fungi in a co-bioreactor

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