Application of the vicinal oxyamination reaction with asymmetric induction to the hemisynthesis of taxol and analogues

Mangatal, L.; Adeline, Marie-Thérèse; Guénard, Daniel; Guéritte-Voegelein, Françoise; Potìer, Pierre

doi:10.1016/s0040-4020(01)81313-2

Cited by 156 publications

(55 citation statements)

References 29 publications

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“…Simultaneous hydrolysis of the N-t-butoxycarbonyl, acetonide, and triethylsilyl protecting groups with formic acid for 30 min at room temp [24] gave Ndebenzoyltaxol (6, 7 mg, overall yield 28% from 1), the identity and purity of which were established by TLC, 500 MHz 1 H NMR spectra, and FAB MS data. The NMR data for 6 and its N-t-butoxycarbonyl derivative (16) corresponded well with the literature values for these known compounds [25,26].…”

Section: Substrates and Reagentssupporting

confidence: 82%

Specificity of the N-benzoyl transferase responsible for the last step of Taxol biosynthesis

Long

Lagisetti

Coates

et al. 2008

Archives of Biochemistry and Biophysics

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The last few steps in the biosynthesis of the anticancer drug Taxol in yew (Taxus) species are thought to involve the attachment of β-phenylalanine to the C13-O-position of the advanced taxane diterpenoid intermediate baccatin III to yield N-debenzoyl-2′-deoxytaxol, followed by hydroxylation on the side chain at the C2′-position to afford N-debenzoyltaxol, and finally N-benzoylation to complete the pathway. A cDNA encoding the N-benzoyl transferase that catalyzes the terminal step of the reaction sequence was previously isolated from a family of transferase clones (derived from an induced Taxus cell cDNA library) by functional characterization of the corresponding recombinant enzyme using the available surrogate substrate N-debenzoyl-2′-deoxytaxol [Walker et al., Proc. Natl. Acad. Sci. USA 99 (2002) 9166-9171]. Semi-synthetic N-debenzoyltaxol was prepared by coupling of 7-triethylsilybaccatin III and (2R,3S)-β-phenylisoserine protected as the N-Boc N,O-isopropylidene derivative by means of carbodiimide activation and formic acid deprotections. The selectivity of the recombinant N-transferase for N-debenzoyltaxol was evaluated, and the enzyme was shown to prefer, by a catalytic efficiency factor of two, N-debenzoyltaxol over N-debenzoyl-2′-deoxytaxol as the taxoid co-substrate in the benzoyl transfer reaction, consistent with the assembly sequence involving 2′-hydroxylation prior to N-benzoylation. Selectivity for the acyl/ aroyl-CoA co-substrate was also examined, and the enzyme was shown to prefer benzoyl CoA. Transfer from tigloyl-CoA to N-debenzoyltaxol to afford cephalomannine (taxol B) was not observed, nor was transfer observed from hexanoyl-CoA or butanoyl-CoA to yield taxol C or taxol D, respectively. These results support the proposed sequence of reactions for C13-O-side chain assembly in Taxol biosynthesis, and suggest that other N-transferases are responsible for the formation of related, late pathway, N-acylated taxoids.

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Section: Substrates and Reagentssupporting

confidence: 82%

Specificity of the N-benzoyl transferase responsible for the last step of Taxol biosynthesis

Long

Lagisetti

Coates

et al. 2008

Archives of Biochemistry and Biophysics

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“…10-Deacetylbaccatin III (DAB, 1) was obtained from Indena, SpA, Italy. 7-Triethylsilylbaccatin III (2), 46,47 26 7,10,13-tri(triethylsilyl)-10-deacetylbaccatin III (7), 23,49 7,10,13-tri(triethylsilyl)-2-debenzoyl-10-deacetylbaccatin III (8), 49,50 7-triethylsilyl-10-deacetyl-10-propanoylbaccatin, 17 and 3'-dephenyl-3'-(2-methyl-1-propenyl)-10-(cyclopropanecarbonyl)docetaxel (19) 17 were prepared by the literature methods.…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of New-Generation Taxoids

et al. 2008

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Novel second-generation taxoids with systematic modifications at the C2, C10, and C3'N positions were synthesized and their structure-activity relationships studied. A number of these taxoids exhibited exceptionally high potentency against multidrug drug-resistant cell lines, and several taxoids exhibited virtually no difference in potency against the drug-sensitive and drug-resistant cell lines. These exceptionally potent taxoids were termed "third-generation taxoids". 19 (SB-T-1214), 14g (SB-T-121303), and 14i (SB-T-1213031), exhibited excellent activity against paclitaxelresistant ovarian cancer cell lines as well, wherein the drug-resistance is mediated by β-tubulin mutation. These taxoids were found to possess exceptional activity in promoting tubulin assembly, forming numerous very short microtubules similar to those formed by discodermolide. Taxoids 19 and 14g also showed excellent cytotoxicity against 4 pancreatic cancer cell lines, expressing 3-4 multidrug resistant genes. Moreover, taxoid 19 exhibited excellent in vivo efficacy against highly drug-resistant CFPAC-1 pancreatic as well as DLD-1 human colon tumor xenografts in mice.

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“…[2][3][4][5][6] Docetaxel (DTX) is a semisynthetic taxoid extract from Taxus baccata (European yew tree) and is one of the most effective drugs in chemotherapy. 7 The mechanism of this drug on cancer cells is through inhibiting microtubule depolymerization, and studies show that the cytotoxic effect of DTX on tumor cells is about two times that of paclitaxel. 8 DTX is used as an effective drug against breast, ovarian, lung, head, and neck cancers [9][10][11] and is available only in the parenteral dosage form (Taxotere; ® sanofi-aventis).…”

Section: Introductionmentioning

confidence: 99%

Thiolated chitosan nanoparticles for enhancing oral absorption of docetaxel: preparation, in vitro and ex vivo evaluation

Saremi

Atyabi

Akhlaghi³

et al. 2011

IJN

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The aim of this study was to prepare and evaluate mucoadhesive core-shell nanoparticles based on copolymerization of thiolated chitosan coated on poly methyl methacrylate cores as a carrier for oral delivery of docetaxel. Docetaxel-loaded nanoparticles with various concentrations were prepared via a radical emulsion polymerization method using cerium ammonium nitrate as an initiator. The physicochemical properties of the obtained nanoparticles were characterized by: dynamic light-scattering analysis for their mean size, size distribution, and zeta potential; scanning electron microscopy and transmission electron microscopy for surface morphology; and differential scanning calorimetry analysis for confirmation of molecular dispersity of docetaxel in the nanoparticles. Nanoparticles were spherical with mean diameter below 200 nm, polydispersity of below 0.15, and positive zeta potential values. The entrapment efficiency of the nanoparticles was approximately 90%. In vitro release studies showed a sustained release characteristic for 10 days after a burst release at the beginning. Ex vivo studies showed a significant increase in the transportation of docetaxel from intestinal membrane of rat when formulated as nanoparticles. Cellular uptake of nanoparticles was investigated using fluoresceinamine-loaded nanoparticles. Docetaxel nanoparticles showed a high cytotoxicity effect in the Caco-2 and MCF-7 cell lines after 72 hours. It can be concluded that by combining the advantages of both thiolated polymers and colloidal particles, these nanoparticles can be proposed as a drug carrier system for mucosal delivery of hydrophobic drugs.

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Application of the vicinal oxyamination reaction with asymmetric induction to the hemisynthesis of taxol and analogues

Cited by 156 publications

References 29 publications

Specificity of the N-benzoyl transferase responsible for the last step of Taxol biosynthesis

Specificity of the N-benzoyl transferase responsible for the last step of Taxol biosynthesis

Design, Synthesis, and Biological Evaluation of New-Generation Taxoids

Thiolated chitosan nanoparticles for enhancing oral absorption of docetaxel: preparation, in vitro and ex vivo evaluation

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