Learning from Peptides to Access Functional Precision Polymer Sequences

Functional precision polymers based on monodisperse oligo(N‐substituted acrylamide)s and oligo(2‐substituted‐α‐hydroxy acid)s have been synthesized. The discrete sequences originate from a direct translation of side‐chain functionality sequences of a peptide with well‐studied properties. The peptide...

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Veröffentlicht in:Angewandte Chemie International Edition Jg. 58; H. 31; S. 10747 - 10751
Hauptverfasser: Maron, Eva, Swisher, Jordan H., Haven, Joris J., Meyer, Tara Y., Junkers, Tanja, Börner, Hans G.
Format: Journal Article
Sprache:Englisch
Veröffentlicht: WEINHEIM Wiley 29.07.2019
Wiley Subscription Services, Inc
Ausgabe:International ed. in English
Schlagworte:
Acrylamide
Additives
Chemistry
Chemistry, Multidisciplinary
drug delivery system
Drug delivery systems
monodisperse polymers
Payloads
peptide PEG conjugates
Peptides
Physical Sciences
Polymers
precision polymers
Science & Technology
sequence design
Solubilization
Substitutes
ACRYLATE OLIGOMERS
peptide PEG conjugates
sequence design
precision polymers
SOLID-PHASE SYNTHESIS
MONODISPERSE
monodisperse polymers
BIOCOMBINATORIAL STRATEGY
COPOLYMERS
drug delivery system
NEXT-GENERATION
ISSN:1433-7851, 1521-3773, 1521-3773
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Abstract Functional precision polymers based on monodisperse oligo(N‐substituted acrylamide)s and oligo(2‐substituted‐α‐hydroxy acid)s have been synthesized. The discrete sequences originate from a direct translation of side‐chain functionality sequences of a peptide with well‐studied properties. The peptide was previously selected to solubilize the photosensitizer meta‐tetra(hydroxyphenyl)chlorin. The resulting peptidomimetic formulation additives preserve the drug solubilization and release characteristics of the parent peptide. In some cases, superior properties are obtained, reaching up to 40 % higher payloads and 27‐times faster initial drug release. Not lost in translation: A new strategy to guide sequence design for accessing functional precision polymers is described. The direct translation of side‐chain functionality sequences into nonpeptidic backbones leads to macromolecules that mimic or improve on the properties of the parent peptide. As an example, the approach was applied to a peptide‐based formulation additive to solubilize a photosensitizer drug.
AbstractList Functional precision polymers based on monodisperse oligo(N-substituted acrylamide)s and oligo(2-substituted-α-hydroxy acid)s have been synthesized. The discrete sequences originate from a direct translation of side-chain functionality sequences of a peptide with well-studied properties. The peptide was previously selected to solubilize the photosensitizer meta-tetra(hydroxyphenyl)chlorin. The resulting peptidomimetic formulation additives preserve the drug solubilization and release characteristics of the parent peptide. In some cases, superior properties are obtained, reaching up to 40 % higher payloads and 27-times faster initial drug release.Functional precision polymers based on monodisperse oligo(N-substituted acrylamide)s and oligo(2-substituted-α-hydroxy acid)s have been synthesized. The discrete sequences originate from a direct translation of side-chain functionality sequences of a peptide with well-studied properties. The peptide was previously selected to solubilize the photosensitizer meta-tetra(hydroxyphenyl)chlorin. The resulting peptidomimetic formulation additives preserve the drug solubilization and release characteristics of the parent peptide. In some cases, superior properties are obtained, reaching up to 40 % higher payloads and 27-times faster initial drug release.
Functional precision polymers based on monodisperse oligo(N-substituted acrylamide)s and oligo(2-substituted-α-hydroxy acid)s have been synthesized. The discrete sequences originate from a direct translation of side-chain functionality sequences of a peptide with well-studied properties. The peptide was previously selected to solubilize the photosensitizer meta-tetra(hydroxyphenyl)chlorin. The resulting peptidomimetic formulation additives preserve the drug solubilization and release characteristics of the parent peptide. In some cases, superior properties are obtained, reaching up to 40 % higher payloads and 27-times faster initial drug release.
Functional precision polymers based on monodisperse oligo(N‐substituted acrylamide)s and oligo(2‐substituted‐α‐hydroxy acid)s have been synthesized. The discrete sequences originate from a direct translation of side‐chain functionality sequences of a peptide with well‐studied properties. The peptide was previously selected to solubilize the photosensitizer meta‐tetra(hydroxyphenyl)chlorin. The resulting peptidomimetic formulation additives preserve the drug solubilization and release characteristics of the parent peptide. In some cases, superior properties are obtained, reaching up to 40 % higher payloads and 27‐times faster initial drug release. Not lost in translation: A new strategy to guide sequence design for accessing functional precision polymers is described. The direct translation of side‐chain functionality sequences into nonpeptidic backbones leads to macromolecules that mimic or improve on the properties of the parent peptide. As an example, the approach was applied to a peptide‐based formulation additive to solubilize a photosensitizer drug.
Functional precision polymers based on monodisperse oligo(N-substituted acrylamide)s and oligo(2-substituted-alpha-hydroxy acid)s have been synthesized. The discrete sequences originate from a direct translation of side-chain functionality sequences of a peptide with well-studied properties. The peptide was previously selected to solubilize the photosensitizer meta-tetra(hydroxyphenyl)chlorin. The resulting peptidomimetic formulation additives preserve the drug solubilization and release characteristics of the parent peptide. In some cases, superior properties are obtained, reaching up to 40 % higher payloads and 27-times faster initial drug release.
Author Maron, Eva
Junkers, Tanja
Börner, Hans G.
Haven, Joris J.
Swisher, Jordan H.
Meyer, Tara Y.
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  fullname: Swisher, Jordan H.
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  surname: Haven
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  organization: Monash University
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  organization: University of Pittsburgh
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  givenname: Hans G.
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  surname: Börner
  fullname: Börner, Hans G.
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  organization: Humboldt-Universität zu Berlin
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Issue 31
Keywords ACRYLATE OLIGOMERS
peptide PEG conjugates
sequence design
precision polymers
SOLID-PHASE SYNTHESIS
MONODISPERSE
monodisperse polymers
BIOCOMBINATORIAL STRATEGY
COPOLYMERS
drug delivery system
NEXT-GENERATION
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Snippet Functional precision polymers based on monodisperse oligo(N‐substituted acrylamide)s and oligo(2‐substituted‐α‐hydroxy acid)s have been synthesized. The...
Functional precision polymers based on monodisperse oligo(N-substituted acrylamide)s and oligo(2-substituted-alpha-hydroxy acid)s have been synthesized. The...
Functional precision polymers based on monodisperse oligo(N-substituted acrylamide)s and oligo(2-substituted-α-hydroxy acid)s have been synthesized. The...
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SubjectTerms Acrylamide
Additives
Chemistry
Chemistry, Multidisciplinary
drug delivery system
Drug delivery systems
monodisperse polymers
Payloads
peptide PEG conjugates
Peptides
Physical Sciences
Polymers
precision polymers
Science & Technology
sequence design
Solubilization
Substitutes
Title Learning from Peptides to Access Functional Precision Polymer Sequences
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201902217
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https://www.ncbi.nlm.nih.gov/pubmed/31020745
https://www.proquest.com/docview/2262689468
https://www.proquest.com/docview/2215023050
Volume 58
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