Synthesis, characterization, and self-assembly with plasmid DNA of a quaternary ammonium derivative of pectic galactan and its fluorescent labeling for bioimaging applications

Ramesh Chintakunta; Nitsa Buaron; Nicole Kahn; Amana Moriah; Rinat Lifshiz; Riki Goldbart; Tamar Traitel; Betty Tyler; Henry Brem; Joseph Kost

doi:10.1016/j.carbpol.2016.05.015

Synthesis, characterization, and self-assembly with plasmid DNA of a quaternary ammonium derivative of pectic galactan and its fluorescent labeling for bioimaging applications

Ramesh Chintakunta, Nitsa Buaron, Nicole Kahn, Amana Moriah, Rinat Lifshiz, Riki Goldbart, Tamar Traitel, Betty Tyler, Henry Brem, Joseph Kost

School of Medicine

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

10 Scopus citations

Abstract

Quaternized derivatives of pectic galactan (QPG) were synthesized by a reaction of pectic galactan (PG) with 3-chloro-2-hydroxypropyl trimethyl ammonium chloride (CHPTAC) in the presence of aqueous sodium hydroxide solution under mild reaction conditions. The results showed that the concentration of CHPTAC and NaOH has great impact on the quaternization reaction. QPG was found to interact electrostatically with plasmid DNA in aqueous solution to form complexes in globular condensed morphology in a nanometer scale size ranging from 60 to 160 nm. Complexes formed with QPG fluorescently labeled with 5-DTAF (QPG-5-DTAF) were introduced to the C6 rat glioma cell line, and were found to be able to enter the cell and approach the nucleus within 24 h. The results suggest that this type of modified natural polysaccharide may have an advantage as a biocompatible and biodegradable gene delivery carrier and furthermore may serve as a cell specific carrier.

Original language	English (US)
Pages (from-to)	308-318
Number of pages	11
Journal	Carbohydrate Polymers
Volume	150
DOIs	https://doi.org/10.1016/j.carbpol.2016.05.015
State	Published - Oct 5 2016

Keywords

5-DTAF
C6 rat glioma cells
CHPTAC
Cell specific carrier
Pectic galactan
Quaternized pectic galactan

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Materials Chemistry

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10.1016/j.carbpol.2016.05.015

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Chintakunta, R., Buaron, N., Kahn, N., Moriah, A., Lifshiz, R., Goldbart, R., Traitel, T., Tyler, B., Brem, H., & Kost, J. (2016). Synthesis, characterization, and self-assembly with plasmid DNA of a quaternary ammonium derivative of pectic galactan and its fluorescent labeling for bioimaging applications. Carbohydrate Polymers, 150, 308-318. https://doi.org/10.1016/j.carbpol.2016.05.015

Chintakunta, R, Buaron, N, Kahn, N, Moriah, A, Lifshiz, R, Goldbart, R, Traitel, T, Tyler, B , Brem, H & Kost, J 2016, 'Synthesis, characterization, and self-assembly with plasmid DNA of a quaternary ammonium derivative of pectic galactan and its fluorescent labeling for bioimaging applications', Carbohydrate Polymers, vol. 150, pp. 308-318. https://doi.org/10.1016/j.carbpol.2016.05.015

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title = "Synthesis, characterization, and self-assembly with plasmid DNA of a quaternary ammonium derivative of pectic galactan and its fluorescent labeling for bioimaging applications",

abstract = "Quaternized derivatives of pectic galactan (QPG) were synthesized by a reaction of pectic galactan (PG) with 3-chloro-2-hydroxypropyl trimethyl ammonium chloride (CHPTAC) in the presence of aqueous sodium hydroxide solution under mild reaction conditions. The results showed that the concentration of CHPTAC and NaOH has great impact on the quaternization reaction. QPG was found to interact electrostatically with plasmid DNA in aqueous solution to form complexes in globular condensed morphology in a nanometer scale size ranging from 60 to 160 nm. Complexes formed with QPG fluorescently labeled with 5-DTAF (QPG-5-DTAF) were introduced to the C6 rat glioma cell line, and were found to be able to enter the cell and approach the nucleus within 24 h. The results suggest that this type of modified natural polysaccharide may have an advantage as a biocompatible and biodegradable gene delivery carrier and furthermore may serve as a cell specific carrier.",

keywords = "5-DTAF, C6 rat glioma cells, CHPTAC, Cell specific carrier, Pectic galactan, Quaternized pectic galactan",

author = "Ramesh Chintakunta and Nitsa Buaron and Nicole Kahn and Amana Moriah and Rinat Lifshiz and Riki Goldbart and Tamar Traitel and Betty Tyler and Henry Brem and Joseph Kost",

note = "Funding Information: This work was supported by the Binational Science Foundation (BSF, United States–Israel, grant number 2009178 ) and Focal Technological Area (FTA) Program of the Israel National Nanotechnology Initiative (INNI). We wish to thank Dr. Nativ-Roth Einat (Ilse Katz Institute for Nanoscale Science and Technology) for the assistance in cryo-TEM imaging. Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.",

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doi = "10.1016/j.carbpol.2016.05.015",

language = "English (US)",

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AU - Chintakunta, Ramesh

AU - Buaron, Nitsa

AU - Kahn, Nicole

AU - Moriah, Amana

AU - Lifshiz, Rinat

AU - Goldbart, Riki

AU - Traitel, Tamar

AU - Tyler, Betty

AU - Brem, Henry

AU - Kost, Joseph

N1 - Funding Information: This work was supported by the Binational Science Foundation (BSF, United States–Israel, grant number 2009178 ) and Focal Technological Area (FTA) Program of the Israel National Nanotechnology Initiative (INNI). We wish to thank Dr. Nativ-Roth Einat (Ilse Katz Institute for Nanoscale Science and Technology) for the assistance in cryo-TEM imaging. Publisher Copyright: © 2016 Elsevier Ltd. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.

PY - 2016/10/5

Y1 - 2016/10/5

N2 - Quaternized derivatives of pectic galactan (QPG) were synthesized by a reaction of pectic galactan (PG) with 3-chloro-2-hydroxypropyl trimethyl ammonium chloride (CHPTAC) in the presence of aqueous sodium hydroxide solution under mild reaction conditions. The results showed that the concentration of CHPTAC and NaOH has great impact on the quaternization reaction. QPG was found to interact electrostatically with plasmid DNA in aqueous solution to form complexes in globular condensed morphology in a nanometer scale size ranging from 60 to 160 nm. Complexes formed with QPG fluorescently labeled with 5-DTAF (QPG-5-DTAF) were introduced to the C6 rat glioma cell line, and were found to be able to enter the cell and approach the nucleus within 24 h. The results suggest that this type of modified natural polysaccharide may have an advantage as a biocompatible and biodegradable gene delivery carrier and furthermore may serve as a cell specific carrier.

AB - Quaternized derivatives of pectic galactan (QPG) were synthesized by a reaction of pectic galactan (PG) with 3-chloro-2-hydroxypropyl trimethyl ammonium chloride (CHPTAC) in the presence of aqueous sodium hydroxide solution under mild reaction conditions. The results showed that the concentration of CHPTAC and NaOH has great impact on the quaternization reaction. QPG was found to interact electrostatically with plasmid DNA in aqueous solution to form complexes in globular condensed morphology in a nanometer scale size ranging from 60 to 160 nm. Complexes formed with QPG fluorescently labeled with 5-DTAF (QPG-5-DTAF) were introduced to the C6 rat glioma cell line, and were found to be able to enter the cell and approach the nucleus within 24 h. The results suggest that this type of modified natural polysaccharide may have an advantage as a biocompatible and biodegradable gene delivery carrier and furthermore may serve as a cell specific carrier.

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KW - C6 rat glioma cells

KW - CHPTAC

KW - Cell specific carrier

KW - Pectic galactan

KW - Quaternized pectic galactan

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Synthesis, characterization, and self-assembly with plasmid DNA of a quaternary ammonium derivative of pectic galactan and its fluorescent labeling for bioimaging applications

Abstract

Keywords

ASJC Scopus subject areas

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