Taxoids: New Weapons against Cancer

Nicolaou, K. C.; Guy, R. Kiplin; Potìer, Pierre

doi:10.1038/scientificamerican0696-94

Cited by 42 publications

(29 citation statements)

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“…These included the mono-and bisacetyl, monoand bis 2,, and bis-triethylsilyl (TES) groups. Although 5-, 13-acetyl, and 5,13-bisacetylbrevifoliol, 2, 3, and 4, 8,14 are known in the literature, they have not been adequately characterized.…”

Section: Resultsmentioning

confidence: 99%

“…2,3 Recently, a lot of attention has been focused on the search for other members of the taxane group 4 that may be directly active or may serve as precursors for the semisynthesis of other active analogues. [5][6][7] The following work describes a detailed characterization of brevifoliol 1, a relatively abundant metabolite isolated from Taxus brevifolia needles (up to 0.30%).…”

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confidence: 99%

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Characterization of an abeo-Taxane: Brevifoliol and Derivatives

et al. 2004

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Brevifoliol is a natural diterpene isolated from Taxus baccata Nutt. A series of brevifoliol 1 derivatives, 2-8 and 10, were prepared for characterization and semisynthesis purposes and included the introduction of acetyl, Troc, and TES groups at C-5 and C-13. Derivatives 16-20 of 5-acetylbrevifoliol 2 were obtained via esterification with cinnamic acid, with both 2S-(-)- and 2R-(+)-3-phenyllactic acid, and with N-benzoyl-(2'R,3'S)-3'-phenylisoserine at C-13. Brevifoliol compounds 12, 13, and 15 with either 2S-(-)-phenyllactate moieties at C-5 and C-13 or an N-benzoyl-(2'R,3'S)-3'-phenylisoserinyl at C-13 were also prepared. An abeo-taxane structure for 1 was clearly defined from the (13)C NMR analysis of the 5-acetyl-13-oxo derivative 8 and from the conversion of 1 into 10, a conformationally restrained compound having a C-13, C-15 oxygen bridge. The biological activity of each of these derivatives is being studied.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Characterization of an abeo-Taxane: Brevifoliol and Derivatives

et al. 2004

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“…Considerable recent attention has focussed on the use induction chemotherapy regimens incorporating taxoids in an attempt to enhance the response to treatment as assessed histologically. The discovery of taxoids has been hailed as the most important advance in the treatment of breast cancer that has occurred in the last 25 years [54,55]. This interest has been generated because of the ability of taxoids to demonstrate an extremely potent anti-cancer action when used as single agents.…”

Section: Alkylating Agentsmentioning

confidence: 99%

Current and Potential Chemotherapeutic Agents Used for Induction Chemotherapy in the Treatment of Breast Cancer

Smith¹,

Hutcheon²,

Heys

2000

CPD

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A substantial proportion of breast cancers are large (<3 cm) or locally advanced (T3, T4, TXN2) at the time of initial presentation. The therapeutic goals that must be achieved in patients with such cancers are to obtain adequate local disease control so that surgery can be performed and to abolish occult distant metastases therefore improving survival. Over the past three decades conventional adjuvant chemotherapy regimens have been employed pre-operatively (neo-adjuvant or primary chemotherapy) to achieve these goals. Studies have now shown that the survival of patients who receive neo-adjuvant chemotherapy is comparable to that of those who receive the same chemotherapy regimen following surgery. It is also apparent that although clinical tumour response rates to neo-adjuvant chemotherapy may be high there is considerable scope for improvement in the corresponding pathological tumour response. Furthermore, data from major studies that have comprehensively evaluated the use of pre-operative chemotherapy now indicates that the pathological response of breast cancers following treatment is of far greater prognostic importance than the clinical response. Recent interests has focoused, therefore, on the implementation of more prolonged or dose intensive chemotherapy regimens with the aims of improving pathological response to treatment and ultimately overall survival. Newer antineoplastic agents are also becoming available that may be used alone or in combination with conventional therapies in order that tumor response may be improved. This review describes current and potential therapeutic agents that may be used for the induction therapy of breast cancer.

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“…In the early 1960s, the National Cancer Institute and the United States Department of Agriculture (USDA) initiated an ambitious program aimed at the discovery of new sources for anticancer drugs (63)(64)(65). Under the aegis of this program, A. Barclay, a botanist from the USDA, collected bark from the pacific yew, Taxus brevifolia Nutt.…”

Section: Taxolmentioning

confidence: 99%

“…The importance of this discovery is profound because the leaves and needles of T. baccata regenerate and thus provide a renewable source of 10-deacetylbaccatin III. Bristol-Myers Squibb employs a semisynthetic process in the commercial production of taxol from 10-deacetylbaccatin III, as does Rhône-Poulenc Rorer for the manufacture of Taxotere (a clinically used analog of taxol in which the PhCO group on the nitrogen atom has been replaced by a t-BuOCO group) (65). Figure 31.…”

Section: Taxolmentioning

confidence: 99%