Paclitaxel-terminated peptide brush polymers

Jialei Zhu; Hao Sun; Cassandra E. Callmann; Matthew P. Thompson; Claudia Battistella; Maria T. Proetto; Andrea S. Carlini; Nathan C. Gianneschi

doi:10.1039/c9cc10023g

Paclitaxel-terminated peptide brush polymers

Jialei Zhu, Hao Sun, Cassandra E. Callmann, Matthew P. Thompson, Claudia Battistella, Maria T. Proetto, Andrea S. Carlini, Nathan C. Gianneschi^*

^*Corresponding author for this work

Chemistry

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

14 Scopus citations

Abstract

In this paper, we report the preparation of paclitaxel-terminated peptide brush polymers wherein cell uptake and toxicity are tunable based on peptide sequence. Synthesis was enabled using a new paclitaxel-containing chain termination agent for ring-opening metathesis polymerization (ROMP). Critically, reverse phase HPLC could be used to efficiently separate peptide brush polymers consisting of one fluorophore and one terminal paclitaxel from crude polymer mixtures. These purified terminally-modified polymers showed greater potency than the original mixtures. Drug-terminated peptide brush polymers carrying positive charges exhibited enhanced cell uptake and cytotoxicity as compared to their neutral and negatively charged analogues.

Original language	English (US)
Pages (from-to)	6778-6781
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	50
DOIs	https://doi.org/10.1039/c9cc10023g
State	Published - Jun 25 2020

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
General Chemistry
Ceramics and Composites
Metals and Alloys
Materials Chemistry
Surfaces, Coatings and Films
Catalysis

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title = "Paclitaxel-terminated peptide brush polymers",

abstract = "In this paper, we report the preparation of paclitaxel-terminated peptide brush polymers wherein cell uptake and toxicity are tunable based on peptide sequence. Synthesis was enabled using a new paclitaxel-containing chain termination agent for ring-opening metathesis polymerization (ROMP). Critically, reverse phase HPLC could be used to efficiently separate peptide brush polymers consisting of one fluorophore and one terminal paclitaxel from crude polymer mixtures. These purified terminally-modified polymers showed greater potency than the original mixtures. Drug-terminated peptide brush polymers carrying positive charges exhibited enhanced cell uptake and cytotoxicity as compared to their neutral and negatively charged analogues.",

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AU - Zhu, Jialei

AU - Sun, Hao

AU - Callmann, Cassandra E.

AU - Thompson, Matthew P.

AU - Battistella, Claudia

AU - Proetto, Maria T.

AU - Carlini, Andrea S.

AU - Gianneschi, Nathan C.

PY - 2020/6/25

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AB - In this paper, we report the preparation of paclitaxel-terminated peptide brush polymers wherein cell uptake and toxicity are tunable based on peptide sequence. Synthesis was enabled using a new paclitaxel-containing chain termination agent for ring-opening metathesis polymerization (ROMP). Critically, reverse phase HPLC could be used to efficiently separate peptide brush polymers consisting of one fluorophore and one terminal paclitaxel from crude polymer mixtures. These purified terminally-modified polymers showed greater potency than the original mixtures. Drug-terminated peptide brush polymers carrying positive charges exhibited enhanced cell uptake and cytotoxicity as compared to their neutral and negatively charged analogues.

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Paclitaxel-terminated peptide brush polymers

Abstract

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