Functionalization of Fatty Acid Vesicles through Newly Synthesized Bolaamphiphile−DNA Conjugates

Michael Wamberg; Rafal Wieczorek; Soren Brier; Jan Willem  de Vries; Minseok Kwak; Andreas Herrmann; Pierre-Alain Monnard

doi:10.1021/bc500289u

Functionalization of Fatty Acid Vesicles through Newly Synthesized Bolaamphiphile−DNA Conjugates

Michael Wamberg, Rafal Wieczorek, Soren Brier, Jan Willem de Vries, Minseok Kwak, Andreas Herrmann, Pierre-Alain Monnard

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

12 Citations (Scopus)

Abstract

The surface functionalization of fatty acid vesicles will allow their use as nanoreactors for complex chemistry. In this report, the tethering of several DNA conjugates to decanoic acid vesicles for molecular recognition and synthetic purposes was explored. Due to the highly dynamic nature of these structures, only one novel bola-amphiphile DNA conjugate could interact efficiently with or spontaneously pierce into the vesicle bilayers without jeopardizing their self-assembly or stability. This molecule was synthesized via a Cu(I)-catalyzed [3 + 2] azide–alkyne cycloaddition (click reaction), and consists of a single hydrocarbon chain of 20 carbons having on one end a triazole group linked to the 5′-phosphate of the nucleic acid and on the other side a hydroxyl-group. Its insertion was so effective that a fluorescent label on the DNA complementary to the conjugate could be used to visualize fatty acid structures.

Original language	English
Pages (from-to)	1678-1688
Number of pages	11
Journal	BIOCONJUGATE CHEMISTRY
Volume	25
Issue number	9
DOIs	https://doi.org/10.1021/bc500289u
Publication status	Published - 21-Aug-2014

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Functionalization of Fatty Acid Vesicles through Newly Synthesized Bolaamphiphile
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title = "Functionalization of Fatty Acid Vesicles through Newly Synthesized Bolaamphiphile−DNA Conjugates",

abstract = "The surface functionalization of fatty acid vesicles will allow their use as nanoreactors for complex chemistry. In this report, the tethering of several DNA conjugates to decanoic acid vesicles for molecular recognition and synthetic purposes was explored. Due to the highly dynamic nature of these structures, only one novel bola-amphiphile DNA conjugate could interact efficiently with or spontaneously pierce into the vesicle bilayers without jeopardizing their self-assembly or stability. This molecule was synthesized via a Cu(I)-catalyzed [3 + 2] azide–alkyne cycloaddition (click reaction), and consists of a single hydrocarbon chain of 20 carbons having on one end a triazole group linked to the 5′-phosphate of the nucleic acid and on the other side a hydroxyl-group. Its insertion was so effective that a fluorescent label on the DNA complementary to the conjugate could be used to visualize fatty acid structures.",

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AU - Wamberg, Michael

AU - Wieczorek, Rafal

AU - Brier, Soren

AU - de Vries, Jan Willem

AU - Kwak, Minseok

AU - Herrmann, Andreas

AU - Monnard, Pierre-Alain

PY - 2014/8/21

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AB - The surface functionalization of fatty acid vesicles will allow their use as nanoreactors for complex chemistry. In this report, the tethering of several DNA conjugates to decanoic acid vesicles for molecular recognition and synthetic purposes was explored. Due to the highly dynamic nature of these structures, only one novel bola-amphiphile DNA conjugate could interact efficiently with or spontaneously pierce into the vesicle bilayers without jeopardizing their self-assembly or stability. This molecule was synthesized via a Cu(I)-catalyzed [3 + 2] azide–alkyne cycloaddition (click reaction), and consists of a single hydrocarbon chain of 20 carbons having on one end a triazole group linked to the 5′-phosphate of the nucleic acid and on the other side a hydroxyl-group. Its insertion was so effective that a fluorescent label on the DNA complementary to the conjugate could be used to visualize fatty acid structures.

U2 - 10.1021/bc500289u

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Functionalization of Fatty Acid Vesicles through Newly Synthesized Bolaamphiphile−DNA Conjugates

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