Design and synthesis of an RGD peptidomimetic-paclitaxel conjugate targeting αvβ3 integrin for tumour-directed drug delivery

Monica Piras; Alexandra Andriu; Andrea Testa; Paul  Wienecke; Ian N Fleming; Matteo Zanda

doi:10.1055/s-0036-1590898

Design and synthesis of an RGD peptidomimetic-paclitaxel conjugate targeting αvβ3 integrin for tumour-directed drug delivery

Monica Piras, Alexandra Andriu, Andrea Testa, Paul Wienecke, Ian N Fleming, Matteo Zanda

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

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Abstract

A 1,2,3-triazole-based RGD peptidomimetic having nanomolar affinity for αvβ3 integrin was conjugated to the potent antimitotic paclitaxel via an oxime heterobifunctional linker. The resulting construct maintained nanomolar binding concentration to αvβ3 integrin and showed 11-fold selectivity in terms of cytotoxicity towards highly αvβ3 expressing U87MG cancer cells relative to non αvβ3 expressing MCF7 cells, indicating promising cancer cell targeting capacity.

Original language	English
Pages (from-to)	2769-2776
Number of pages	8
Journal	Synlett
Volume	28
Issue number	20
Early online date	1 Sep 2017
DOIs	https://doi.org/10.1055/s-0036-1590898
Publication status	Published - 2017

Keywords

RGD
peptidomimetic
integrin
paclitaxel
click
cytotoxicity
cancer

UN SDGs

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

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© Georg Thieme Verlag Stuttgart · New York
Accepted author manuscript, 1.11 MBLicence: Other

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title = "Design and synthesis of an RGD peptidomimetic-paclitaxel conjugate targeting αvβ3 integrin for tumour-directed drug delivery",

abstract = "A 1,2,3-triazole-based RGD peptidomimetic having nanomolar affinity for αvβ3 integrin was conjugated to the potent antimitotic paclitaxel via an oxime heterobifunctional linker. The resulting construct maintained nanomolar binding concentration to αvβ3 integrin and showed 11-fold selectivity in terms of cytotoxicity towards highly αvβ3 expressing U87MG cancer cells relative to non αvβ3 expressing MCF7 cells, indicating promising cancer cell targeting capacity.",

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author = "Monica Piras and Alexandra Andriu and Andrea Testa and Paul Wienecke and Fleming, {Ian N} and Matteo Zanda",

note = "We thank the Development Trust, University of Aberdeen, for funding a fellowship to M.P. and a studentship to A.A. Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590898.",

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doi = "10.1055/s-0036-1590898",

language = "English",

volume = "28",

pages = "2769--2776",

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T1 - Design and synthesis of an RGD peptidomimetic-paclitaxel conjugate targeting αvβ3 integrin for tumour-directed drug delivery

AU - Piras, Monica

AU - Andriu, Alexandra

AU - Testa, Andrea

AU - Wienecke, Paul

AU - Fleming, Ian N

AU - Zanda, Matteo

N1 - We thank the Development Trust, University of Aberdeen, for funding a fellowship to M.P. and a studentship to A.A. Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590898.

PY - 2017

Y1 - 2017

N2 - A 1,2,3-triazole-based RGD peptidomimetic having nanomolar affinity for αvβ3 integrin was conjugated to the potent antimitotic paclitaxel via an oxime heterobifunctional linker. The resulting construct maintained nanomolar binding concentration to αvβ3 integrin and showed 11-fold selectivity in terms of cytotoxicity towards highly αvβ3 expressing U87MG cancer cells relative to non αvβ3 expressing MCF7 cells, indicating promising cancer cell targeting capacity.

AB - A 1,2,3-triazole-based RGD peptidomimetic having nanomolar affinity for αvβ3 integrin was conjugated to the potent antimitotic paclitaxel via an oxime heterobifunctional linker. The resulting construct maintained nanomolar binding concentration to αvβ3 integrin and showed 11-fold selectivity in terms of cytotoxicity towards highly αvβ3 expressing U87MG cancer cells relative to non αvβ3 expressing MCF7 cells, indicating promising cancer cell targeting capacity.

KW - RGD

KW - peptidomimetic

KW - integrin

KW - paclitaxel

KW - click

KW - cytotoxicity

KW - cancer

U2 - 10.1055/s-0036-1590898

DO - 10.1055/s-0036-1590898

M3 - Article

VL - 28

SP - 2769

EP - 2776

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 20

ER -

Design and synthesis of an RGD peptidomimetic-paclitaxel conjugate targeting αvβ3 integrin for tumour-directed drug delivery

Abstract

Keywords

UN SDGs

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