Flow and Microwave-Assisted Synthesis of N-(Triethylene glycol)glycine Oligomers and Their Remarkable Cellular Transporter Activities.
Identifieur interne : 001789 ( Main/Exploration ); précédent : 001788; suivant : 001790Flow and Microwave-Assisted Synthesis of N-(Triethylene glycol)glycine Oligomers and Their Remarkable Cellular Transporter Activities.
Auteurs : Thingsoon Jong [Royaume-Uni] ; Ana M. Pérez-L Pez [Royaume-Uni] ; Emma M V. Johansson [Royaume-Uni] ; Annamaria Lilienkampf [Royaume-Uni] ; Mark Bradley [Royaume-Uni]Source :
- Bioconjugate chemistry [ 1520-4812 ] ; 2015.
Descripteurs français
- KwdFr :
- Cellules HEK293, Cellules HeLa, Cellules cultivées, Conception de médicament, Glycine (), Humains, Lysine (), Micro-ondes, Peptides de pénétration cellulaire (), Peptides de pénétration cellulaire (pharmacocinétique), Peptidomimétiques (), Peptoïdes (), Peptoïdes (pharmacocinétique), Polyéthylène glycols (), Répartition dans les tissus, Transport biologique.
- MESH :
- pharmacocinétique : Peptides de pénétration cellulaire, Peptoïdes.
- Cellules HEK293, Cellules HeLa, Cellules cultivées, Conception de médicament, Glycine, Humains, Lysine, Micro-ondes, Peptides de pénétration cellulaire, Peptidomimétiques, Peptoïdes, Polyéthylène glycols, Répartition dans les tissus, Transport biologique.
English descriptors
- KwdEn :
- Biological Transport, Cell-Penetrating Peptides (chemistry), Cell-Penetrating Peptides (pharmacokinetics), Cells, Cultured, Drug Design, Glycine (chemistry), HEK293 Cells, HeLa Cells, Humans, Lysine (chemistry), Microwaves, Peptidomimetics (chemistry), Peptoids (chemistry), Peptoids (pharmacokinetics), Polyethylene Glycols (chemistry), Tissue Distribution.
- MESH :
- chemical , chemistry : Cell-Penetrating Peptides, Glycine, Lysine, Peptidomimetics, Peptoids, Polyethylene Glycols.
- chemical , pharmacokinetics : Cell-Penetrating Peptides, Peptoids.
- Biological Transport, Cells, Cultured, Drug Design, HEK293 Cells, HeLa Cells, Humans, Microwaves, Tissue Distribution.
Abstract
Peptidomimetics, such as oligo-N-alkylglycines (peptoids), are attractive alternatives to traditional cationic cell-penetrating peptides (such as R9) due to their robust proteolytic stability and reduced cellular toxicity. Here, monomeric N-alkylglycines, incorporating amino-functionalized hexyl or triethylene glycol (TEG) side chains, were synthesized via a three-step continuous-flow reaction sequence, giving the monomers N-Fmoc-(6-Boc-aminohexyl)glycine and N-Fmoc-((2-(2-Boc-aminoethoxy)ethoxy)ethyl)glycine in 49% and 41% overall yields, respectively. These were converted into oligomers (5, 7, and 9-mers) using an Fmoc-based solid-phase protocol and evaluated as cellular transporters. Hybrid oligomers, constructed of alternating units of the aminohexyl and amino-TEG monomers, were non-cytotoxic and exhibited remarkable cellular uptake activity compared to the analogous fully TEG or lysine-like compounds.
DOI: 10.1021/acs.bioconjchem.5b00307
PubMed: 26155805
Affiliations:
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Peptides</term><term>Peptoids</term></keywords><keywords scheme="MESH" qualifier="pharmacocinétique" xml:lang="fr"><term>Peptides de pénétration cellulaire</term><term>Peptoïdes</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Biological Transport</term><term>Cells, Cultured</term><term>Drug Design</term><term>HEK293 Cells</term><term>HeLa Cells</term><term>Humans</term><term>Microwaves</term><term>Tissue Distribution</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Cellules HEK293</term><term>Cellules HeLa</term><term>Cellules cultivées</term><term>Conception de médicament</term><term>Glycine</term><term>Humains</term><term>Lysine</term><term>Micro-ondes</term><term>Peptides de pénétration cellulaire</term><term>Peptidomimétiques</term><term>Peptoïdes</term><term>Polyéthylène glycols</term><term>Répartition dans les tissus</term><term>Transport biologique</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Peptidomimetics, such as oligo-N-alkylglycines (peptoids), are attractive alternatives to traditional cationic cell-penetrating peptides (such as R9) due to their robust proteolytic stability and reduced cellular toxicity. Here, monomeric N-alkylglycines, incorporating amino-functionalized hexyl or triethylene glycol (TEG) side chains, were synthesized via a three-step continuous-flow reaction sequence, giving the monomers N-Fmoc-(6-Boc-aminohexyl)glycine and N-Fmoc-((2-(2-Boc-aminoethoxy)ethoxy)ethyl)glycine in 49% and 41% overall yields, respectively. These were converted into oligomers (5, 7, and 9-mers) using an Fmoc-based solid-phase protocol and evaluated as cellular transporters. Hybrid oligomers, constructed of alternating units of the aminohexyl and amino-TEG monomers, were non-cytotoxic and exhibited remarkable cellular uptake activity compared to the analogous fully TEG or lysine-like compounds. </div></front></TEI><affiliations><list><country><li>Royaume-Uni</li></country><region><li>Écosse</li></region><settlement><li>Édimbourg</li></settlement><orgName><li>Université d'Édimbourg</li></orgName></list><tree><country name="Royaume-Uni"><region name="Écosse"><name sortKey="Jong, Thingsoon" sort="Jong, Thingsoon" uniqKey="Jong T" first="Thingsoon" last="Jong">Thingsoon Jong</name></region><name sortKey="Bradley, Mark" sort="Bradley, Mark" uniqKey="Bradley M" first="Mark" last="Bradley">Mark Bradley</name><name sortKey="Johansson, Emma M V" sort="Johansson, Emma M V" uniqKey="Johansson E" first="Emma M V" last="Johansson">Emma M V. Johansson</name><name sortKey="Lilienkampf, Annamaria" sort="Lilienkampf, Annamaria" uniqKey="Lilienkampf A" first="Annamaria" last="Lilienkampf">Annamaria Lilienkampf</name><name sortKey="Perez L Pez, Ana M" sort="Perez L Pez, Ana M" uniqKey="Perez L Pez A" first="Ana M" last="Pérez-L Pez">Ana M. Pérez-L Pez</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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