Cargando…

Carbodiimide‐Driven Dimerization and Self‐Assembly of Artificial, Ribose‐Based Amphiphiles

The aqueous self‐assembly of amphiphiles into aggregates such as micelles and vesicles has been widely investigated over the past decades with applications ranging from materials science to drug delivery. The combination of characteristic properties of nucleic acids and amphiphiles is of substantial...

Descripción completa

Detalles Bibliográficos
Autores principales: Sun, Jing, Vogel, Julian, Chen, Lisa, Schleper, A. Lennart, Bergner, Tim, Kuehne, Alexander J. C., von Delius, Max
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9303926/
https://www.ncbi.nlm.nih.gov/pubmed/35038189
http://dx.doi.org/10.1002/chem.202104116
_version_ 1784751985855037440
author Sun, Jing
Vogel, Julian
Chen, Lisa
Schleper, A. Lennart
Bergner, Tim
Kuehne, Alexander J. C.
von Delius, Max
author_facet Sun, Jing
Vogel, Julian
Chen, Lisa
Schleper, A. Lennart
Bergner, Tim
Kuehne, Alexander J. C.
von Delius, Max
author_sort Sun, Jing
collection PubMed
description The aqueous self‐assembly of amphiphiles into aggregates such as micelles and vesicles has been widely investigated over the past decades with applications ranging from materials science to drug delivery. The combination of characteristic properties of nucleic acids and amphiphiles is of substantial interest to mimic biological self‐organization and compartmentalization. Herein, we present ribose‐ and ribonucleotide‐based amphiphiles and investigate their self‐assembly as well as their fundamental reactivity. We found that various types of aggregates are formed, ranging in size from nanometers to micrometers and all amphiphiles exhibit aggregation‐induced emission (AIE) in solution as well as in the solid state. We also observed that the addition of 1‐ethyl‐3‐(3‐dimethylaminopropyl)carbodiimide (EDC) leads to rapid and selective dimerization of the amphiphiles into pyrophosphates, which decreases the critical aggregation concentration (CAC) by a factor of 25 when compared to the monomers. Since the propensity for amphiphile dimerization is correlated with their tendency to self‐assemble, our results may be relevant for the formation of rudimentary compartments under prebiotic conditions.
format Online
Article
Text
id pubmed-9303926
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-93039262022-07-28 Carbodiimide‐Driven Dimerization and Self‐Assembly of Artificial, Ribose‐Based Amphiphiles Sun, Jing Vogel, Julian Chen, Lisa Schleper, A. Lennart Bergner, Tim Kuehne, Alexander J. C. von Delius, Max Chemistry Research Articles The aqueous self‐assembly of amphiphiles into aggregates such as micelles and vesicles has been widely investigated over the past decades with applications ranging from materials science to drug delivery. The combination of characteristic properties of nucleic acids and amphiphiles is of substantial interest to mimic biological self‐organization and compartmentalization. Herein, we present ribose‐ and ribonucleotide‐based amphiphiles and investigate their self‐assembly as well as their fundamental reactivity. We found that various types of aggregates are formed, ranging in size from nanometers to micrometers and all amphiphiles exhibit aggregation‐induced emission (AIE) in solution as well as in the solid state. We also observed that the addition of 1‐ethyl‐3‐(3‐dimethylaminopropyl)carbodiimide (EDC) leads to rapid and selective dimerization of the amphiphiles into pyrophosphates, which decreases the critical aggregation concentration (CAC) by a factor of 25 when compared to the monomers. Since the propensity for amphiphile dimerization is correlated with their tendency to self‐assemble, our results may be relevant for the formation of rudimentary compartments under prebiotic conditions. John Wiley and Sons Inc. 2022-02-08 2022-03-01 /pmc/articles/PMC9303926/ /pubmed/35038189 http://dx.doi.org/10.1002/chem.202104116 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Sun, Jing
Vogel, Julian
Chen, Lisa
Schleper, A. Lennart
Bergner, Tim
Kuehne, Alexander J. C.
von Delius, Max
Carbodiimide‐Driven Dimerization and Self‐Assembly of Artificial, Ribose‐Based Amphiphiles
title Carbodiimide‐Driven Dimerization and Self‐Assembly of Artificial, Ribose‐Based Amphiphiles
title_full Carbodiimide‐Driven Dimerization and Self‐Assembly of Artificial, Ribose‐Based Amphiphiles
title_fullStr Carbodiimide‐Driven Dimerization and Self‐Assembly of Artificial, Ribose‐Based Amphiphiles
title_full_unstemmed Carbodiimide‐Driven Dimerization and Self‐Assembly of Artificial, Ribose‐Based Amphiphiles
title_short Carbodiimide‐Driven Dimerization and Self‐Assembly of Artificial, Ribose‐Based Amphiphiles
title_sort carbodiimide‐driven dimerization and self‐assembly of artificial, ribose‐based amphiphiles
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9303926/
https://www.ncbi.nlm.nih.gov/pubmed/35038189
http://dx.doi.org/10.1002/chem.202104116
work_keys_str_mv AT sunjing carbodiimidedrivendimerizationandselfassemblyofartificialribosebasedamphiphiles
AT vogeljulian carbodiimidedrivendimerizationandselfassemblyofartificialribosebasedamphiphiles
AT chenlisa carbodiimidedrivendimerizationandselfassemblyofartificialribosebasedamphiphiles
AT schleperalennart carbodiimidedrivendimerizationandselfassemblyofartificialribosebasedamphiphiles
AT bergnertim carbodiimidedrivendimerizationandselfassemblyofartificialribosebasedamphiphiles
AT kuehnealexanderjc carbodiimidedrivendimerizationandselfassemblyofartificialribosebasedamphiphiles
AT vondeliusmax carbodiimidedrivendimerizationandselfassemblyofartificialribosebasedamphiphiles