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

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

5 Citations (Scopus)

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 PC3 and MCF7 cell lines

Original language	English
Pages (from-to)	8343-8347
Number of pages	5
Journal	Tetrahedron
Volume	70
Issue number	44
Early online date	6 Sep 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

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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 affinitycomparable to RGD reference compounds, and all released NO by the Griess test assay. Two analogues exhibited significant cytotoxic effects against PC3 and MCF7 cell lines ",

keywords = "anticancer, RGD peptide, nitric oxide, abiraterone",

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

note = "We thank CRUK for a Studentship (A.N.) and Dr. Terry K. Smith (St. Andrews University) for access to a Microplate reader.",

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

language = "English",

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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

N1 - We thank CRUK for a Studentship (A.N.) and Dr. Terry K. Smith (St. Andrews University) for access to a Microplate reader.

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 affinitycomparable to RGD reference compounds, and all released NO by the Griess test assay. Two analogues exhibited significant cytotoxic effects against PC3 and MCF7 cell lines

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 affinitycomparable to RGD reference compounds, and all released NO by the Griess test assay. Two analogues exhibited significant cytotoxic effects against PC3 and MCF7 cell lines

KW - anticancer

KW - RGD peptide

KW - nitric oxide

KW - abiraterone

U2 - 10.1016/j.tet.2014.09.004

DO - 10.1016/j.tet.2014.09.004

M3 - Article

VL - 70

SP - 8343

EP - 8347

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 44

ER -