Synthesis of 7- and 10-spermine conjugates of paclitaxel and 10-deacetyl-paclitaxel as potential prodrugs

Arturo Battaglia; Andrea Guerrini; Eleonora Baldelli; Gabriele Fontana; Greta Varchi; Cristian Samorì; Ezio Bombardelli

doi:10.1016/j.tetlet.2006.02.108

Synthesis of 7- and 10-spermine conjugates of paclitaxel and 10-deacetyl-paclitaxel as potential prodrugs

Arturo Battaglia, Andrea Guerrini, Eleonora Baldelli, Gabriele Fontana, Greta Varchi, Cristian Samorì, Ezio Bombardelli

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

15 Scopus citations

Abstract

Efficient syntheses of two taxol analogs bearing the linear polyamine spermine at 7- and 10-positions of paclitaxel and 10-deacetyl-paclitaxel have been developed. These polyamine-taxol-conjugates were isolated as water soluble difluoride salts. The aim of the present work was to introduce a chemical modification into taxol skeleton in order to increase drug selectivity toward tumor cells. The cytotoxic activity of these conjugates was evaluated in MCF7 and MCF7-R cell lines. The observed low cytotoxicity suggests that these conjugates could act as potential prodrugs.

Original language	English (US)
Pages (from-to)	2667-2670
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	16
DOIs	https://doi.org/10.1016/j.tetlet.2006.02.108
State	Published - Apr 17 2006

Keywords

Antitumor
Paclitaxel
Prodrug conjugates
Spermine

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.02.108

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abstract = "Efficient syntheses of two taxol analogs bearing the linear polyamine spermine at 7- and 10-positions of paclitaxel and 10-deacetyl-paclitaxel have been developed. These polyamine-taxol-conjugates were isolated as water soluble difluoride salts. The aim of the present work was to introduce a chemical modification into taxol skeleton in order to increase drug selectivity toward tumor cells. The cytotoxic activity of these conjugates was evaluated in MCF7 and MCF7-R cell lines. The observed low cytotoxicity suggests that these conjugates could act as potential prodrugs.",

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T1 - Synthesis of 7- and 10-spermine conjugates of paclitaxel and 10-deacetyl-paclitaxel as potential prodrugs

AU - Battaglia, Arturo

AU - Guerrini, Andrea

AU - Baldelli, Eleonora

AU - Fontana, Gabriele

AU - Varchi, Greta

AU - Samorì, Cristian

AU - Bombardelli, Ezio

PY - 2006/4/17

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N2 - Efficient syntheses of two taxol analogs bearing the linear polyamine spermine at 7- and 10-positions of paclitaxel and 10-deacetyl-paclitaxel have been developed. These polyamine-taxol-conjugates were isolated as water soluble difluoride salts. The aim of the present work was to introduce a chemical modification into taxol skeleton in order to increase drug selectivity toward tumor cells. The cytotoxic activity of these conjugates was evaluated in MCF7 and MCF7-R cell lines. The observed low cytotoxicity suggests that these conjugates could act as potential prodrugs.

AB - Efficient syntheses of two taxol analogs bearing the linear polyamine spermine at 7- and 10-positions of paclitaxel and 10-deacetyl-paclitaxel have been developed. These polyamine-taxol-conjugates were isolated as water soluble difluoride salts. The aim of the present work was to introduce a chemical modification into taxol skeleton in order to increase drug selectivity toward tumor cells. The cytotoxic activity of these conjugates was evaluated in MCF7 and MCF7-R cell lines. The observed low cytotoxicity suggests that these conjugates could act as potential prodrugs.

KW - Antitumor

KW - Paclitaxel

KW - Prodrug conjugates

KW - Spermine

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Synthesis of 7- and 10-spermine conjugates of paclitaxel and 10-deacetyl-paclitaxel as potential prodrugs

Abstract

Keywords

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