Synthesis and characteristics of biodegradable pyridinium amphiphiles used for in vitro DNA delivery

Astrid Roosjen; Jarmila Smisterova; Cecile Driessen; Joachim T. Anders; Anno Wagenaar; Dirk Hoekstra; Ron Hulst; Jan B.F.N. Engberts

Synthesis and characteristics of biodegradable pyridinium amphiphiles used for in vitro DNA delivery

Astrid Roosjen, Jarmila Smisterova, Cecile Driessen, Joachim T. Anders, Anno Wagenaar, Dirk Hoekstra, Ron Hulst, Jan B.F.N. Engberts

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Abstract

Pyridinium amphiphiles have found practical application for the delivery of DNA into eukaryotic cells. A general synthetic method starting from (iso)nicotinoyl chloride has been devised for the preparation of pyridinium amphiphiles based on (bio)degradable esters, allowing structural variation both in the hydrophobic part and in the headgroup area. By means of differential scanning calorimetry, transmission electron microscopy and UV measurements, some characteristics, including hydrolytic behaviour, have been determined. In vitro transfection ability and toxicity have been determined using the eukaryotic COS-7 cell line.

Original language	English
Pages (from-to)	1271-1277
Number of pages	7
Journal	European Journal of Organic Chemistry
Issue number	7
Publication status	Published - 2002

Keywords

cationic amphiphiles
nitrogen heterocycles
transfection
vesicles
GENE-THERAPY DEATH
CATIONIC AMPHIPHILES
MAMMALIAN-CELLS
TRANSFECTION
COMPLEXES
EFFICIENT
LIPIDS
VECTOR

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Roosjen, A., Smisterova, J., Driessen, C., Anders, J. T., Wagenaar, A., Hoekstra, D., Hulst, R., & Engberts, J. B. F. N. (2002). Synthesis and characteristics of biodegradable pyridinium amphiphiles used for in vitro DNA delivery. European Journal of Organic Chemistry, (7), 1271-1277. http://onlinelibrary.wiley.com/doi/10.1002/1099-0690(200204)2002:7%3C1271::AID-EJOC1271%3E3.0.CO;2-G/pdf

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title = "Synthesis and characteristics of biodegradable pyridinium amphiphiles used for in vitro DNA delivery",

abstract = "Pyridinium amphiphiles have found practical application for the delivery of DNA into eukaryotic cells. A general synthetic method starting from (iso)nicotinoyl chloride has been devised for the preparation of pyridinium amphiphiles based on (bio)degradable esters, allowing structural variation both in the hydrophobic part and in the headgroup area. By means of differential scanning calorimetry, transmission electron microscopy and UV measurements, some characteristics, including hydrolytic behaviour, have been determined. In vitro transfection ability and toxicity have been determined using the eukaryotic COS-7 cell line.",

keywords = "cationic amphiphiles, nitrogen heterocycles, transfection, vesicles, GENE-THERAPY DEATH, CATIONIC AMPHIPHILES, MAMMALIAN-CELLS, TRANSFECTION, COMPLEXES, EFFICIENT, LIPIDS, VECTOR",

author = "Astrid Roosjen and Jarmila Smisterova and Cecile Driessen and Anders, {Joachim T.} and Anno Wagenaar and Dirk Hoekstra and Ron Hulst and Engberts, {Jan B.F.N.}",

note = "Relation: http://www.rug.nl/scheikunde/ date_submitted:2005 Rights: University of Groningen. Stratingh Institute",

year = "2002",

language = "English",

pages = "1271--1277",

journal = "European Journal of Organic Chemistry",

publisher = "WILEY-V C H VERLAG GMBH",

number = "7",

}

Roosjen, A, Smisterova, J, Driessen, C, Anders, JT, Wagenaar, A, Hoekstra, D, Hulst, R & Engberts, JBFN 2002, 'Synthesis and characteristics of biodegradable pyridinium amphiphiles used for in vitro DNA delivery', European Journal of Organic Chemistry, no. 7, pp. 1271-1277. <http://onlinelibrary.wiley.com/doi/10.1002/1099-0690(200204)2002:7%3C1271::AID-EJOC1271%3E3.0.CO;2-G/pdf>

TY - JOUR

T1 - Synthesis and characteristics of biodegradable pyridinium amphiphiles used for in vitro DNA delivery

AU - Roosjen, Astrid

AU - Smisterova, Jarmila

AU - Driessen, Cecile

AU - Anders, Joachim T.

AU - Wagenaar, Anno

AU - Hoekstra, Dirk

AU - Hulst, Ron

AU - Engberts, Jan B.F.N.

N1 - Relation: http://www.rug.nl/scheikunde/ date_submitted:2005 Rights: University of Groningen. Stratingh Institute

PY - 2002

Y1 - 2002

N2 - Pyridinium amphiphiles have found practical application for the delivery of DNA into eukaryotic cells. A general synthetic method starting from (iso)nicotinoyl chloride has been devised for the preparation of pyridinium amphiphiles based on (bio)degradable esters, allowing structural variation both in the hydrophobic part and in the headgroup area. By means of differential scanning calorimetry, transmission electron microscopy and UV measurements, some characteristics, including hydrolytic behaviour, have been determined. In vitro transfection ability and toxicity have been determined using the eukaryotic COS-7 cell line.

AB - Pyridinium amphiphiles have found practical application for the delivery of DNA into eukaryotic cells. A general synthetic method starting from (iso)nicotinoyl chloride has been devised for the preparation of pyridinium amphiphiles based on (bio)degradable esters, allowing structural variation both in the hydrophobic part and in the headgroup area. By means of differential scanning calorimetry, transmission electron microscopy and UV measurements, some characteristics, including hydrolytic behaviour, have been determined. In vitro transfection ability and toxicity have been determined using the eukaryotic COS-7 cell line.

KW - cationic amphiphiles

KW - nitrogen heterocycles

KW - transfection

KW - vesicles

KW - GENE-THERAPY DEATH

KW - CATIONIC AMPHIPHILES

KW - MAMMALIAN-CELLS

KW - TRANSFECTION

KW - COMPLEXES

KW - EFFICIENT

KW - LIPIDS

KW - VECTOR

M3 - Article

SP - 1271

EP - 1277

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 7

ER -

Synthesis and characteristics of biodegradable pyridinium amphiphiles used for in vitro DNA delivery

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Keywords

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