Improved proteolytic stability and potent activity against Leishmania infantum trypanothione reductase of α/β-peptide foldamers conjugated to cell-penetrating peptides.
Identifieur interne : 000D41 ( Main/Exploration ); précédent : 000D40; suivant : 000D42Improved proteolytic stability and potent activity against Leishmania infantum trypanothione reductase of α/β-peptide foldamers conjugated to cell-penetrating peptides.
Auteurs : Héctor De Lucio [Espagne] ; Ana María Gamo [Espagne] ; Marta Ruiz-Santaquiteria [Espagne] ; Sonia De Castro [Espagne] ; Pedro A. Sánchez-Murcia [Espagne] ; Miguel A. Toro [Espagne] ; Kilian Jesús Gutiérrez [Espagne] ; Federico Gago [Espagne] ; Antonio Jiménez-Ruiz [Espagne] ; María-José Camarasa [Espagne] ; Sonsoles Velázquez [Espagne]Source :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2017.
Descripteurs français
- KwdFr :
- MESH :
- administration et posologie : Peptides de pénétration cellulaire.
- antagonistes et inhibiteurs : NADH, NADPH oxidoreductases.
- enzymologie : Leishmania infantum.
- Animaux, Peptides de pénétration cellulaire, Protéolyse, Séquence d'acides aminés.
English descriptors
- KwdEn :
- MESH :
- chemical , administration & dosage : Cell-Penetrating Peptides.
- chemical , antagonists & inhibitors : NADH, NADPH Oxidoreductases.
- chemical , chemistry : Cell-Penetrating Peptides.
- enzymology : Leishmania infantum.
- Amino Acid Sequence, Animals, Proteolysis.
Abstract
The objective of the current study was to enhance the proteolytic stability of peptide-based inhibitors that target critical protein-protein interactions at the dimerization interface of Leishmania infantum trypanothione reductase (Li-TryR) using a backbone modification strategy. To achieve this goal we carried out the synthesis, proteolytic stability studies and biological evaluation of a small library of α/β3-peptide foldamers of different length (from 9-mers to 13-mers) and different α→β substitution patterns related to prototype linear α-peptides. We show that several 13-residue α/β3-peptide foldamers retain inhibitory potency against the enzyme (in both activity and dimerization assays) while they are far less susceptible to proteolytic degradation than an analogous α-peptide. The strong dependence of the binding affinities for Li-TryR on the length of the α,β-peptides is supported by theoretical calculations on conformational ensembles of the resulting complexes. The conjugation of the most proteolytically stable α/β-peptide with oligoarginines results in a molecule with potent activity against L. infantum promastigotes and amastigotes.
DOI: 10.1016/j.ejmech.2017.09.032
PubMed: 29017116
Affiliations:
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Le document en format XML
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Sánchez-Murcia</name><affiliation wicri:level="3"><nlm:affiliation>Área de Farmacología, Departamento de Ciencias Biomédicas, Unidad Asociada Al IQM-CSIC, Universidad de Alcalá, E-28805 Alcalá de Henares, Madrid, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Área de Farmacología, Departamento de Ciencias Biomédicas, Unidad Asociada Al IQM-CSIC, Universidad de Alcalá, E-28805 Alcalá de Henares, Madrid</wicri:regionArea><placeName><settlement type="city">Madrid</settlement><region nuts="2" type="region">Communauté de Madrid</region></placeName></affiliation></author><author><name sortKey="Toro, Miguel A" sort="Toro, Miguel A" uniqKey="Toro M" first="Miguel A" last="Toro">Miguel A. Toro</name><affiliation wicri:level="3"><nlm:affiliation>Departamento de Biología de Sistemas, Universidad de Alcalá, E-28805 Alcalá de Henares, Madrid, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Departamento de Biología de Sistemas, Universidad de Alcalá, E-28805 Alcalá de Henares, Madrid</wicri:regionArea><placeName><settlement type="city">Madrid</settlement><region nuts="2" type="region">Communauté de Madrid</region></placeName></affiliation></author><author><name sortKey="Gutierrez, Kilian Jesus" sort="Gutierrez, Kilian Jesus" uniqKey="Gutierrez K" first="Kilian Jesús" last="Gutiérrez">Kilian Jesús Gutiérrez</name><affiliation wicri:level="3"><nlm:affiliation>Departamento de Biología de Sistemas, Universidad de Alcalá, E-28805 Alcalá de Henares, Madrid, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Departamento de Biología de Sistemas, Universidad de Alcalá, E-28805 Alcalá de Henares, Madrid</wicri:regionArea><placeName><settlement type="city">Madrid</settlement><region nuts="2" type="region">Communauté de Madrid</region></placeName></affiliation></author><author><name sortKey="Gago, Federico" sort="Gago, Federico" uniqKey="Gago F" first="Federico" last="Gago">Federico Gago</name><affiliation wicri:level="3"><nlm:affiliation>Área de Farmacología, Departamento de Ciencias Biomédicas, Unidad Asociada Al IQM-CSIC, Universidad de Alcalá, E-28805 Alcalá de Henares, Madrid, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Área de Farmacología, Departamento de Ciencias Biomédicas, Unidad Asociada Al IQM-CSIC, Universidad de Alcalá, E-28805 Alcalá de Henares, Madrid</wicri:regionArea><placeName><settlement type="city">Madrid</settlement><region nuts="2" type="region">Communauté de Madrid</region></placeName></affiliation></author><author><name sortKey="Jimenez Ruiz, Antonio" sort="Jimenez Ruiz, Antonio" uniqKey="Jimenez Ruiz A" first="Antonio" last="Jiménez-Ruiz">Antonio Jiménez-Ruiz</name><affiliation wicri:level="3"><nlm:affiliation>Departamento de Biología de Sistemas, Universidad de Alcalá, E-28805 Alcalá de Henares, Madrid, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Departamento de Biología de Sistemas, Universidad de Alcalá, E-28805 Alcalá de Henares, Madrid</wicri:regionArea><placeName><settlement type="city">Madrid</settlement><region nuts="2" type="region">Communauté de Madrid</region></placeName></affiliation></author><author><name sortKey="Camarasa, Maria Jose" sort="Camarasa, Maria Jose" uniqKey="Camarasa M" first="María-José" last="Camarasa">María-José Camarasa</name><affiliation wicri:level="2"><nlm:affiliation>Instituto de Química Médica (IQM-CSIC), E-28006 Madrid, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Instituto de Química Médica (IQM-CSIC), E-28006 Madrid</wicri:regionArea><placeName><region nuts="2" type="communauté">Communauté de Madrid</region></placeName></affiliation></author><author><name sortKey="Velazquez, Sonsoles" sort="Velazquez, Sonsoles" uniqKey="Velazquez S" first="Sonsoles" last="Velázquez">Sonsoles Velázquez</name><affiliation wicri:level="2"><nlm:affiliation>Instituto de Química Médica (IQM-CSIC), E-28006 Madrid, Spain. Electronic address: iqmsv29@iqm.csic.es.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Instituto de Química Médica (IQM-CSIC), E-28006 Madrid</wicri:regionArea><placeName><region nuts="2" type="communauté">Communauté de Madrid</region></placeName></affiliation></author></analytic><series><title level="j">European journal of medicinal chemistry</title><idno type="eISSN">1768-3254</idno><imprint><date when="2017" type="published">2017</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amino Acid Sequence</term><term>Animals</term><term>Cell-Penetrating Peptides (administration & dosage)</term><term>Cell-Penetrating Peptides (chemistry)</term><term>Leishmania infantum (enzymology)</term><term>NADH, NADPH Oxidoreductases (antagonists & inhibitors)</term><term>Proteolysis</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term><term>Leishmania infantum (enzymologie)</term><term>NADH, NADPH oxidoreductases (antagonistes et inhibiteurs)</term><term>Peptides de pénétration cellulaire ()</term><term>Peptides de pénétration cellulaire (administration et posologie)</term><term>Protéolyse</term><term>Séquence d'acides aminés</term></keywords><keywords scheme="MESH" type="chemical" qualifier="administration & dosage" xml:lang="en"><term>Cell-Penetrating Peptides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>NADH, NADPH Oxidoreductases</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Cell-Penetrating Peptides</term></keywords><keywords scheme="MESH" qualifier="administration et posologie" xml:lang="fr"><term>Peptides de pénétration cellulaire</term></keywords><keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>NADH, NADPH oxidoreductases</term></keywords><keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr"><term>Leishmania infantum</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>Leishmania infantum</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Amino Acid Sequence</term><term>Animals</term><term>Proteolysis</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Animaux</term><term>Peptides de pénétration cellulaire</term><term>Protéolyse</term><term>Séquence d'acides aminés</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The objective of the current study was to enhance the proteolytic stability of peptide-based inhibitors that target critical protein-protein interactions at the dimerization interface of Leishmania infantum trypanothione reductase (Li-TryR) using a backbone modification strategy. To achieve this goal we carried out the synthesis, proteolytic stability studies and biological evaluation of a small library of α/β<sup>3</sup>-peptide foldamers of different length (from 9-mers to 13-mers) and different α→β substitution patterns related to prototype linear α-peptides. We show that several 13-residue α/β<sup>3</sup>-peptide foldamers retain inhibitory potency against the enzyme (in both activity and dimerization assays) while they are far less susceptible to proteolytic degradation than an analogous α-peptide. The strong dependence of the binding affinities for Li-TryR on the length of the α,β-peptides is supported by theoretical calculations on conformational ensembles of the resulting complexes. The conjugation of the most proteolytically stable α/β-peptide with oligoarginines results in a molecule with potent activity against L. infantum promastigotes and amastigotes.</div></front></TEI><affiliations><list><country><li>Espagne</li></country><region><li>Communauté de Madrid</li></region><settlement><li>Madrid</li></settlement></list><tree><country name="Espagne"><region name="Communauté de Madrid"><name sortKey="De Lucio, Hector" sort="De Lucio, Hector" uniqKey="De Lucio H" first="Héctor" last="De Lucio">Héctor De Lucio</name></region><name sortKey="Camarasa, Maria Jose" sort="Camarasa, Maria Jose" uniqKey="Camarasa M" first="María-José" last="Camarasa">María-José Camarasa</name><name sortKey="De Castro, Sonia" sort="De Castro, Sonia" uniqKey="De Castro S" first="Sonia" last="De Castro">Sonia De Castro</name><name sortKey="Gago, Federico" sort="Gago, Federico" uniqKey="Gago F" first="Federico" last="Gago">Federico Gago</name><name sortKey="Gamo, Ana Maria" sort="Gamo, Ana Maria" uniqKey="Gamo A" first="Ana María" last="Gamo">Ana María Gamo</name><name sortKey="Gutierrez, Kilian Jesus" sort="Gutierrez, Kilian Jesus" uniqKey="Gutierrez K" first="Kilian Jesús" last="Gutiérrez">Kilian Jesús Gutiérrez</name><name sortKey="Jimenez Ruiz, Antonio" sort="Jimenez Ruiz, Antonio" uniqKey="Jimenez Ruiz A" first="Antonio" last="Jiménez-Ruiz">Antonio Jiménez-Ruiz</name><name sortKey="Ruiz Santaquiteria, Marta" sort="Ruiz Santaquiteria, Marta" uniqKey="Ruiz Santaquiteria M" first="Marta" last="Ruiz-Santaquiteria">Marta Ruiz-Santaquiteria</name><name sortKey="Sanchez Murcia, Pedro A" sort="Sanchez Murcia, Pedro A" uniqKey="Sanchez Murcia P" first="Pedro A" last="Sánchez-Murcia">Pedro A. Sánchez-Murcia</name><name sortKey="Toro, Miguel A" sort="Toro, Miguel A" uniqKey="Toro M" first="Miguel A" last="Toro">Miguel A. Toro</name><name sortKey="Velazquez, Sonsoles" sort="Velazquez, Sonsoles" uniqKey="Velazquez S" first="Sonsoles" last="Velázquez">Sonsoles Velázquez</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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