Toward Angiogenesis Inhibitors Based on the Conjugation of Organometallic Platinum(II) Complexes to RGD Peptides

A novel conjugate between a cyclometalated platinum(II) complex with dual antiangiogenic and antitumor activity and a cyclic peptide containing the RGD sequence (‐Arg‐Gly‐Asp‐) has been synthesized by combining solid‐ and solution‐phase methodologies. Although peptide conjugation rendered a non‐cyto...

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Published inChemMedChem Vol. 13; no. 17; pp. 1755 - 1762
Main Authors Zamora, Ana, Gandioso, Albert, Massaguer, Anna, Buenestado, Silvia, Calvis, Carme, Hernández, Jose Luis, Mitjans, Francesc, Rodríguez, Venancio, Ruiz, José, Marchán, Vicente
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 06.09.2018
Wiley Subscription Services, Inc
Wiley-VCH
Subjects
Angiogenesis
Angiogenesis inhibitors
Angiogenesis Inhibitors - chemical synthesis
Angiogenesis Inhibitors - chemistry
Angiogenesis Inhibitors - pharmacology
Angiogènesi
Antiangiogenics
Anticancer properties
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antitumor activity
Cancer
Cell Line, Tumor
Cell Proliferation - drug effects
Chemistry, Medicinal
Compostos organometàl·lics
Conjugates
Conjugation
Cytotoxicity
Càncer
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Endothelial cells
Human Umbilical Vein Endothelial Cells - drug effects
Humans
Inhibitors
Life Sciences & Biomedicine
Molecular Structure
Neovascularization
Neovascularization, Pathologic - drug therapy
Neovascularization, Pathologic - pathology
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Oligopeptides - pharmacology
Organometallic compounds
Organoplatinum Compounds - chemical synthesis
Organoplatinum Compounds - chemistry
Organoplatinum Compounds - pharmacology
Peptides
Pharmacology & Pharmacy
Platinum
Pèptids
Receptors
Science & Technology
Structure-Activity Relationship
Tumor cell lines
Umbilical vein
inhibitors
APOPTOSIS
angiogenesis
peptides
ANTITUMOR
CILENGITIDE
STRATEGIES
platinum
ANTIANGIOGENIC ACTIVITY
RUTHENIUM(II)
cancer
AGENTS
IRIDIUM COMPLEX
INTEGRIN ALPHA(V)BETA ANTAGONISTS
Online AccessGet full text
ISSN1860-7179
1860-7187
1860-7187
DOI10.1002/cmdc.201800282

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Abstract A novel conjugate between a cyclometalated platinum(II) complex with dual antiangiogenic and antitumor activity and a cyclic peptide containing the RGD sequence (‐Arg‐Gly‐Asp‐) has been synthesized by combining solid‐ and solution‐phase methodologies. Although peptide conjugation rendered a non‐cytotoxic compound in all tested tumor cell lines (± αVβ3 and αVβ5 integrin receptors), the antiangiogenic activity of the Pt‐c(RGDfK) conjugate in human umbilical vein endothelial cells at sub‐cytotoxic concentrations opens the way to the design of a novel class of angiogenesis inhibitors through conjugation of metallodrugs with high antiangiogenic activity to cyclic RGD‐containing peptides or peptidomimetic analogues. Platinum‐backed peptides: Conjugates of cyclometalated platinum(II) complexes and RGD peptides are investigated as potential angiogenesis inhibitors. The antiangiogenic activity of the Pt‐c(RGDfK) conjugate in human umbilical vein endothelial cells at sub‐cytotoxic concentrations opens the way to the design of angiogenesis inhibitors through conjugation of metallodrugs with high antiangiogenic activity to cyclic RGD‐containing peptides or peptidomimetic analogues.
AbstractList A novel conjugate between a cyclometalated platinum(II) complex with dual antiangiogenic and antitumor activity and a cyclic peptide containing the RGD sequence (-Arg-Gly-Asp-) has been synthesized by combining solid- and solution-phase methodologies. Although peptide conjugation rendered a non-cytotoxic compound in all tested tumor cell lines (± αV β3 and αV β5 integrin receptors), the antiangiogenic activity of the Pt-c(RGDfK) conjugate in human umbilical vein endothelial cells at sub-cytotoxic concentrations opens the way to the design of a novel class of angiogenesis inhibitors through conjugation of metallodrugs with high antiangiogenic activity to cyclic RGD-containing peptides or peptidomimetic analogues.A novel conjugate between a cyclometalated platinum(II) complex with dual antiangiogenic and antitumor activity and a cyclic peptide containing the RGD sequence (-Arg-Gly-Asp-) has been synthesized by combining solid- and solution-phase methodologies. Although peptide conjugation rendered a non-cytotoxic compound in all tested tumor cell lines (± αV β3 and αV β5 integrin receptors), the antiangiogenic activity of the Pt-c(RGDfK) conjugate in human umbilical vein endothelial cells at sub-cytotoxic concentrations opens the way to the design of a novel class of angiogenesis inhibitors through conjugation of metallodrugs with high antiangiogenic activity to cyclic RGD-containing peptides or peptidomimetic analogues.
A novel conjugate between a cyclometalated platinum(II) complex with dual antiangiogenic and antitumor activity and a cyclic peptide containing the RGD sequence (‐Arg‐Gly‐Asp‐) has been synthesized by combining solid‐ and solution‐phase methodologies. Although peptide conjugation rendered a non‐cytotoxic compound in all tested tumor cell lines (± α V β 3 and α V β 5 integrin receptors), the antiangiogenic activity of the Pt‐c(RGDfK) conjugate in human umbilical vein endothelial cells at sub‐cytotoxic concentrations opens the way to the design of a novel class of angiogenesis inhibitors through conjugation of metallodrugs with high antiangiogenic activity to cyclic RGD‐containing peptides or peptidomimetic analogues.
A novel conjugate between a cyclometalated platinum(II) complex with dual antiangiogenic and antitumor activity and a cyclic peptide containing the RGD sequence (‐Arg‐Gly‐Asp‐) has been synthesized by combining solid‐ and solution‐phase methodologies. Although peptide conjugation rendered a non‐cytotoxic compound in all tested tumor cell lines (± αVβ3 and αVβ5 integrin receptors), the antiangiogenic activity of the Pt‐c(RGDfK) conjugate in human umbilical vein endothelial cells at sub‐cytotoxic concentrations opens the way to the design of a novel class of angiogenesis inhibitors through conjugation of metallodrugs with high antiangiogenic activity to cyclic RGD‐containing peptides or peptidomimetic analogues. Platinum‐backed peptides: Conjugates of cyclometalated platinum(II) complexes and RGD peptides are investigated as potential angiogenesis inhibitors. The antiangiogenic activity of the Pt‐c(RGDfK) conjugate in human umbilical vein endothelial cells at sub‐cytotoxic concentrations opens the way to the design of angiogenesis inhibitors through conjugation of metallodrugs with high antiangiogenic activity to cyclic RGD‐containing peptides or peptidomimetic analogues.
A novel conjugate between a cyclometalated platinum(II) complex with dual antiangiogenic and antitumor activity and a cyclic peptide containing the RGD sequence (‐Arg‐Gly‐Asp‐) has been synthesized by combining solid‐ and solution‐phase methodologies. Although peptide conjugation rendered a non‐cytotoxic compound in all tested tumor cell lines (± αVβ3 and αVβ5 integrin receptors), the antiangiogenic activity of the Pt‐c(RGDfK) conjugate in human umbilical vein endothelial cells at sub‐cytotoxic concentrations opens the way to the design of a novel class of angiogenesis inhibitors through conjugation of metallodrugs with high antiangiogenic activity to cyclic RGD‐containing peptides or peptidomimetic analogues.
A novel conjugate between a cyclometalated platinum(II) complex with dual antiangiogenic and antitumor activity and a cyclic peptide containing the RGD sequence (-Arg-Gly-Asp-) has been synthesized by combining solid- and solution-phase methodologies. Although peptide conjugation rendered a non-cytotoxic compound in all tested tumor cell lines (+/- (V3) and (V5) integrin receptors), the antiangiogenic activity of the Pt-c(RGDfK) conjugate in human umbilical vein endothelial cells at sub-cytotoxic concentrations opens the way to the design of a novel class of angiogenesis inhibitors through conjugation of metallodrugs with high antiangiogenic activity to cyclic RGD-containing peptides or peptidomimetic analogues.
A novel conjugate between a cyclometalated platinum(II) complex with dual antiangiogenic and antitumor activity and a cyclic peptide containing the RGD sequence (-Arg-Gly-Asp-) has been synthesized by combining solid- and solution-phase methodologies. Although peptide conjugation rendered a non-cytotoxic compound in all tested tumor cell lines (± αV β3 and αV β5 integrin receptors), the antiangiogenic activity of the Pt-c(RGDfK) conjugate in human umbilical vein endothelial cells at sub-cytotoxic concentrations opens the way to the design of a novel class of angiogenesis inhibitors through conjugation of metallodrugs with high antiangiogenic activity to cyclic RGD-containing peptides or peptidomimetic analogues.
A novel conjugate between a cyclometalated platinum(II) complex with dual antiangiogenic and antitumor activity and a cyclic peptide containing the RGD sequence (-Arg-Gly-Asp-) has been synthesized by combining solid- and solution-phase methodologies. Although peptide conjugation rendered a non-cytotoxic compound in all tested tumor cell lines (± α β and α β integrin receptors), the antiangiogenic activity of the Pt-c(RGDfK) conjugate in human umbilical vein endothelial cells at sub-cytotoxic concentrations opens the way to the design of a novel class of angiogenesis inhibitors through conjugation of metallodrugs with high antiangiogenic activity to cyclic RGD-containing peptides or peptidomimetic analogues.
Author Zamora, Ana
Buenestado, Silvia
Calvis, Carme
Rodríguez, Venancio
Hernández, Jose Luis
Marchán, Vicente
Massaguer, Anna
Gandioso, Albert
Mitjans, Francesc
Ruiz, José
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Issue 17
Keywords inhibitors
APOPTOSIS
angiogenesis
peptides
ANTITUMOR
CILENGITIDE
STRATEGIES
platinum
ANTIANGIOGENIC ACTIVITY
RUTHENIUM(II)
cancer
AGENTS
IRIDIUM COMPLEX
INTEGRIN ALPHA(V)BETA ANTAGONISTS
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Snippet A novel conjugate between a cyclometalated platinum(II) complex with dual antiangiogenic and antitumor activity and a cyclic peptide containing the RGD...
Source Web of Science
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SubjectTerms Angiogenesis
Angiogenesis inhibitors
Angiogenesis Inhibitors - chemical synthesis
Angiogenesis Inhibitors - chemistry
Angiogenesis Inhibitors - pharmacology
Angiogènesi
Antiangiogenics
Anticancer properties
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antitumor activity
Cancer
Cell Line, Tumor
Cell Proliferation - drug effects
Chemistry, Medicinal
Compostos organometàl·lics
Conjugates
Conjugation
Cytotoxicity
Càncer
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Endothelial cells
Human Umbilical Vein Endothelial Cells - drug effects
Humans
Inhibitors
Life Sciences & Biomedicine
Molecular Structure
Neovascularization
Neovascularization, Pathologic - drug therapy
Neovascularization, Pathologic - pathology
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Oligopeptides - pharmacology
Organometallic compounds
Organoplatinum Compounds - chemical synthesis
Organoplatinum Compounds - chemistry
Organoplatinum Compounds - pharmacology
Peptides
Pharmacology & Pharmacy
Platinum
Pèptids
Receptors
Science & Technology
Structure-Activity Relationship
Tumor cell lines
Umbilical vein
Title Toward Angiogenesis Inhibitors Based on the Conjugation of Organometallic Platinum(II) Complexes to RGD Peptides
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fcmdc.201800282
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000443804600004
https://www.ncbi.nlm.nih.gov/pubmed/29932312
https://www.proquest.com/docview/2099786650
https://www.proquest.com/docview/2058503699
https://recercat.cat/handle/2072/333308
Volume 13
WOS 000443804600004
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