Synthesis, tubulin assembly, and antiproliferative activity against MCF7 and NCI/ADR-RES cancer cells of 10-O-acetyl-5′-hydroxybutitaxel

Haibo Ge; Jianmei Wang; Margaret M. Kayser; Richard H. Himes; Gunda I. Georg

doi:10.1016/j.bmcl.2008.10.010

Synthesis, tubulin assembly, and antiproliferative activity against MCF7 and NCI/ADR-RES cancer cells of 10-O-acetyl-5′-hydroxybutitaxel

Haibo Ge, Jianmei Wang, Margaret M. Kayser, Richard H. Himes, Gunda I. Georg

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

A highly efficient kinetic resolution of racemic cis-4-(2-tert-butyldimethylsilyloxy-1,1-dimethyl)ethyl-3-tert-butyldimethylsilyloxy-azetidin-2-one with 7-O-triethylsilylbaccatin III was carried out to furnish 10-O-acetyl-5′-hydroxybutitaxel after removal of the silyl protecting groups. The compound was 50% as active as paclitaxel in a tubulin assembly assay and showed significantly decreased activity against MCF7 cell proliferation compared to paclitaxel.

Original language	English (US)
Pages (from-to)	6165-6167
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	23
DOIs	https://doi.org/10.1016/j.bmcl.2008.10.010
State	Published - Dec 1 2008

Bibliographical note

Funding Information:
The authors wish to thank the National Cancer Institute for financial support of this research (NIH CA82801 and NIH CA105305), NBIF Research Assistantship Initiative, and Tapestry Pharmaceuticals (Boulder, CO) for a generous gift of 10-deacetylbaccatin III. We wish to thank Christopher Schneider for his help with the HPLC analysis. We also thank Jacquelyn K. Huff for her excellent technical assistance.

Keywords

Cytotoxicity
Kinetic resolution
MCF7
NCI/ADR RES
Paclitaxel analogues
Semisynthesis
Tubulin assembly

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "Synthesis, tubulin assembly, and antiproliferative activity against MCF7 and NCI/ADR-RES cancer cells of 10-O-acetyl-5′-hydroxybutitaxel",

abstract = "A highly efficient kinetic resolution of racemic cis-4-(2-tert-butyldimethylsilyloxy-1,1-dimethyl)ethyl-3-tert-butyldimethylsilyloxy-azetidin-2-one with 7-O-triethylsilylbaccatin III was carried out to furnish 10-O-acetyl-5′-hydroxybutitaxel after removal of the silyl protecting groups. The compound was 50% as active as paclitaxel in a tubulin assembly assay and showed significantly decreased activity against MCF7 cell proliferation compared to paclitaxel.",

keywords = "Cytotoxicity, Kinetic resolution, MCF7, NCI/ADR RES, Paclitaxel analogues, Semisynthesis, Tubulin assembly",

author = "Haibo Ge and Jianmei Wang and Kayser, {Margaret M.} and Himes, {Richard H.} and Georg, {Gunda I.}",

note = "Funding Information: The authors wish to thank the National Cancer Institute for financial support of this research (NIH CA82801 and NIH CA105305), NBIF Research Assistantship Initiative, and Tapestry Pharmaceuticals (Boulder, CO) for a generous gift of 10-deacetylbaccatin III. We wish to thank Christopher Schneider for his help with the HPLC analysis. We also thank Jacquelyn K. Huff for her excellent technical assistance. ",

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doi = "10.1016/j.bmcl.2008.10.010",

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AU - Ge, Haibo

AU - Wang, Jianmei

AU - Kayser, Margaret M.

AU - Himes, Richard H.

AU - Georg, Gunda I.

N1 - Funding Information: The authors wish to thank the National Cancer Institute for financial support of this research (NIH CA82801 and NIH CA105305), NBIF Research Assistantship Initiative, and Tapestry Pharmaceuticals (Boulder, CO) for a generous gift of 10-deacetylbaccatin III. We wish to thank Christopher Schneider for his help with the HPLC analysis. We also thank Jacquelyn K. Huff for her excellent technical assistance.

PY - 2008/12/1

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N2 - A highly efficient kinetic resolution of racemic cis-4-(2-tert-butyldimethylsilyloxy-1,1-dimethyl)ethyl-3-tert-butyldimethylsilyloxy-azetidin-2-one with 7-O-triethylsilylbaccatin III was carried out to furnish 10-O-acetyl-5′-hydroxybutitaxel after removal of the silyl protecting groups. The compound was 50% as active as paclitaxel in a tubulin assembly assay and showed significantly decreased activity against MCF7 cell proliferation compared to paclitaxel.

AB - A highly efficient kinetic resolution of racemic cis-4-(2-tert-butyldimethylsilyloxy-1,1-dimethyl)ethyl-3-tert-butyldimethylsilyloxy-azetidin-2-one with 7-O-triethylsilylbaccatin III was carried out to furnish 10-O-acetyl-5′-hydroxybutitaxel after removal of the silyl protecting groups. The compound was 50% as active as paclitaxel in a tubulin assembly assay and showed significantly decreased activity against MCF7 cell proliferation compared to paclitaxel.

KW - Cytotoxicity

KW - Kinetic resolution

KW - MCF7

KW - NCI/ADR RES

KW - Paclitaxel analogues

KW - Semisynthesis

KW - Tubulin assembly

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JO - Bioorganic and Medicinal Chemistry Letters

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ER -

Synthesis, tubulin assembly, and antiproliferative activity against MCF7 and NCI/ADR-RES cancer cells of 10-O-acetyl-5′-hydroxybutitaxel

Abstract

Bibliographical note

Keywords

UN SDGs

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