Design Principles of Lipid-like Ionic Liquids for Gene Delivery

David J. Siegel; Grace I. Anderson; Lauren M. Paul; Philipp J. Seibert; Patrick C. Hillesheim; Yinghong Sheng; Matthias Zeller; Andreas Taubert; Peter Werner; Christian Balischewski; Scott F. Michael; Arsalan Mirjafari

doi:10.1021/acsabm.1c00252

Design Principles of Lipid-like Ionic Liquids for Gene Delivery

David J. Siegel
, Grace I. Anderson
, Lauren M. Paul
, Philipp J. Seibert
, Patrick C. Hillesheim
, Yinghong Sheng
, Matthias Zeller
, Andreas Taubert
, Peter Werner
, Christian Balischewski
, Scott F. Michael
, Arsalan Mirjafari

Chemistry

SUNY Oswego

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

We developed lipid-like ionic liquids, containing 2-mercaptoimidazolium and 2-mercaptothiazolinium headgroups tethered to two long saturated alkyl chains, as carriers for in vitro delivery of plasmid HEK DNA into 293T cells. We employed a combination of modular design, synthesis, X-ray analysis, and computational modeling to rationalize the self-assembly and desired physicochemical and biological properties. The results suggest that thioamide-derived ionic liquids may serve as a modular platform for lipid-mediated gene delivery. This work represents a step toward understanding the structure-function relationships of these amphiphiles with long-range ordering and offering insight into design principles for synthetic vectors based on self-assembly behavior.

Original language	English
Pages (from-to)	4737-4743
Number of pages	7
Journal	ACS Applied Bio Materials
Volume	4
Issue number	6
DOIs	https://doi.org/10.1021/acsabm.1c00252
State	Published - Jun 21 2021

Keywords

DNA delivery
biomaterials
cationic lipids
gene therapy
ionic liquids
lipid-like materials
nonviral vectors

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10.1021/acsabm.1c00252

Cite this

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title = "Design Principles of Lipid-like Ionic Liquids for Gene Delivery",

abstract = "We developed lipid-like ionic liquids, containing 2-mercaptoimidazolium and 2-mercaptothiazolinium headgroups tethered to two long saturated alkyl chains, as carriers for in vitro delivery of plasmid HEK DNA into 293T cells. We employed a combination of modular design, synthesis, X-ray analysis, and computational modeling to rationalize the self-assembly and desired physicochemical and biological properties. The results suggest that thioamide-derived ionic liquids may serve as a modular platform for lipid-mediated gene delivery. This work represents a step toward understanding the structure-function relationships of these amphiphiles with long-range ordering and offering insight into design principles for synthetic vectors based on self-assembly behavior.",

keywords = "DNA delivery, biomaterials, cationic lipids, gene therapy, ionic liquids, lipid-like materials, nonviral vectors",

author = "Siegel, \{David J.\} and Anderson, \{Grace I.\} and Paul, \{Lauren M.\} and Seibert, \{Philipp J.\} and Hillesheim, \{Patrick C.\} and Yinghong Sheng and Matthias Zeller and Andreas Taubert and Peter Werner and Christian Balischewski and Michael, \{Scott F.\} and Arsalan Mirjafari",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = jun,

day = "21",

doi = "10.1021/acsabm.1c00252",

language = "English",

volume = "4",

pages = "4737--4743",

journal = "ACS Applied Bio Materials",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Design Principles of Lipid-like Ionic Liquids for Gene Delivery

AU - Siegel, David J.

AU - Anderson, Grace I.

AU - Paul, Lauren M.

AU - Seibert, Philipp J.

AU - Hillesheim, Patrick C.

AU - Sheng, Yinghong

AU - Zeller, Matthias

AU - Taubert, Andreas

AU - Werner, Peter

AU - Balischewski, Christian

AU - Michael, Scott F.

AU - Mirjafari, Arsalan

PY - 2021/6/21

Y1 - 2021/6/21

N2 - We developed lipid-like ionic liquids, containing 2-mercaptoimidazolium and 2-mercaptothiazolinium headgroups tethered to two long saturated alkyl chains, as carriers for in vitro delivery of plasmid HEK DNA into 293T cells. We employed a combination of modular design, synthesis, X-ray analysis, and computational modeling to rationalize the self-assembly and desired physicochemical and biological properties. The results suggest that thioamide-derived ionic liquids may serve as a modular platform for lipid-mediated gene delivery. This work represents a step toward understanding the structure-function relationships of these amphiphiles with long-range ordering and offering insight into design principles for synthetic vectors based on self-assembly behavior.

AB - We developed lipid-like ionic liquids, containing 2-mercaptoimidazolium and 2-mercaptothiazolinium headgroups tethered to two long saturated alkyl chains, as carriers for in vitro delivery of plasmid HEK DNA into 293T cells. We employed a combination of modular design, synthesis, X-ray analysis, and computational modeling to rationalize the self-assembly and desired physicochemical and biological properties. The results suggest that thioamide-derived ionic liquids may serve as a modular platform for lipid-mediated gene delivery. This work represents a step toward understanding the structure-function relationships of these amphiphiles with long-range ordering and offering insight into design principles for synthetic vectors based on self-assembly behavior.

KW - DNA delivery

KW - biomaterials

KW - cationic lipids

KW - gene therapy

KW - ionic liquids

KW - lipid-like materials

KW - nonviral vectors

UR - https://www.scopus.com/pages/publications/85108577530

U2 - 10.1021/acsabm.1c00252

DO - 10.1021/acsabm.1c00252

M3 - Article

C2 - 35007023

SN - 2576-6422

VL - 4

SP - 4737

EP - 4743

JO - ACS Applied Bio Materials

JF - ACS Applied Bio Materials

IS - 6

ER -

Design Principles of Lipid-like Ionic Liquids for Gene Delivery

Abstract

Keywords

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