Synthesis and anticancer properties of RGD peptides conjugated to nitric oxide releasing functional groups and abiraterone

Andrew Nortcliffe; Ian N. Fleming; Nigel P. Botting; David O'Hagan

doi:10.1016/j.tet.2014.09.004

Synthesis and anticancer properties of RGD peptides conjugated to nitric oxide releasing functional groups and abiraterone

Andrew Nortcliffe, Ian N. Fleming, Nigel P. Botting, David O'Hagan^*

^*Corresponding author for this work

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

Abstract

A series of analogues of the integrin binding aspartic acid-glycine-arginine (RGD) peptide sequence were synthesised conjugated to nitric oxide (NO) donating functional groups. Also the cytotoxicity of abiraterone, a prostate cancer drug, was explored when it was conjugated in three part constructs to RGD sequences and NO releasing heterocycles. In general the analogues showed integrin binding affinity comparable to RGD reference compounds, and all released NO by the Griess test assay. Two analogues exhibited significant cytotoxic effects against PO and MCF7 cell lines. (C) 2014 Published by Elsevier Ltd.

Original language	English
Pages (from-to)	8343-8347
Number of pages	5
Journal	Tetrahedron
Volume	70
Issue number	44
Early online date	6 Sept 2014
DOIs	https://doi.org/10.1016/j.tet.2014.09.004
Publication status	Published - 4 Nov 2014

Keywords

Anticancer
RGD peptide
Nitric oxide
Abiraterone
Prostate-cancer
Biological evaluation
Cell-adhesion
Integrin
ALPHA(V)BETA(3)
Hypoxia
Fibronectin
Mechanism
Sulindac
Analogs

UN SDGs

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

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10.1016/j.tet.2014.09.004

Cite this

@article{cdb086e829e44a5a9feac96dbca7a761,

title = "Synthesis and anticancer properties of RGD peptides conjugated to nitric oxide releasing functional groups and abiraterone",

abstract = "A series of analogues of the integrin binding aspartic acid-glycine-arginine (RGD) peptide sequence were synthesised conjugated to nitric oxide (NO) donating functional groups. Also the cytotoxicity of abiraterone, a prostate cancer drug, was explored when it was conjugated in three part constructs to RGD sequences and NO releasing heterocycles. In general the analogues showed integrin binding affinity comparable to RGD reference compounds, and all released NO by the Griess test assay. Two analogues exhibited significant cytotoxic effects against PO and MCF7 cell lines. (C) 2014 Published by Elsevier Ltd.",

keywords = "Anticancer, RGD peptide, Nitric oxide, Abiraterone, Prostate-cancer, Biological evaluation, Cell-adhesion, Integrin, ALPHA(V)BETA(3), Hypoxia, Fibronectin, Mechanism, Sulindac, Analogs",

author = "Andrew Nortcliffe and Fleming, {Ian N.} and Botting, {Nigel P.} and David O'Hagan",

year = "2014",

month = nov,

day = "4",

doi = "10.1016/j.tet.2014.09.004",

language = "English",

volume = "70",

pages = "8343--8347",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "44",

}

TY - JOUR

T1 - Synthesis and anticancer properties of RGD peptides conjugated to nitric oxide releasing functional groups and abiraterone

AU - Nortcliffe, Andrew

AU - Fleming, Ian N.

AU - Botting, Nigel P.

AU - O'Hagan, David

PY - 2014/11/4

Y1 - 2014/11/4

N2 - A series of analogues of the integrin binding aspartic acid-glycine-arginine (RGD) peptide sequence were synthesised conjugated to nitric oxide (NO) donating functional groups. Also the cytotoxicity of abiraterone, a prostate cancer drug, was explored when it was conjugated in three part constructs to RGD sequences and NO releasing heterocycles. In general the analogues showed integrin binding affinity comparable to RGD reference compounds, and all released NO by the Griess test assay. Two analogues exhibited significant cytotoxic effects against PO and MCF7 cell lines. (C) 2014 Published by Elsevier Ltd.

AB - A series of analogues of the integrin binding aspartic acid-glycine-arginine (RGD) peptide sequence were synthesised conjugated to nitric oxide (NO) donating functional groups. Also the cytotoxicity of abiraterone, a prostate cancer drug, was explored when it was conjugated in three part constructs to RGD sequences and NO releasing heterocycles. In general the analogues showed integrin binding affinity comparable to RGD reference compounds, and all released NO by the Griess test assay. Two analogues exhibited significant cytotoxic effects against PO and MCF7 cell lines. (C) 2014 Published by Elsevier Ltd.

KW - Anticancer

KW - RGD peptide

KW - Nitric oxide

KW - Abiraterone

KW - Prostate-cancer

KW - Biological evaluation

KW - Cell-adhesion

KW - Integrin

KW - ALPHA(V)BETA(3)

KW - Hypoxia

KW - Fibronectin

KW - Mechanism

KW - Sulindac

KW - Analogs

UR - http://www.sciencedirect.com/science/article/pii/S0040402014012836#appd001

U2 - 10.1016/j.tet.2014.09.004

DO - 10.1016/j.tet.2014.09.004

M3 - Article

SN - 0040-4020

VL - 70

SP - 8343

EP - 8347

JO - Tetrahedron

JF - Tetrahedron

IS - 44

ER -

Synthesis and anticancer properties of RGD peptides conjugated to nitric oxide releasing functional groups and abiraterone

Abstract

Keywords

UN SDGs

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Extending fluorinase C-18F-bond: Extending fluorinase [C-18F]-bond biocatalysis for Positron Emission Tomography (PET)

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Synthesis and anticancer properties of RGD peptides conjugated to nitric oxide releasing functional groups and abiraterone

Abstract

Keywords

UN SDGs

Access to Document

Other files and links

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Projects

Extending fluorinase C-18F-bond: Extending fluorinase [C-18F]-bond biocatalysis for Positron Emission Tomography (PET)

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