Poly(l-aspartic acid) derivative soluble in a volatile organic solvent for biomedical application

Nam Muk Oh; Kyung Taek Oh; Yu Seok Youn; Eun Seong Lee

doi:10.1016/j.colsurfb.2012.03.024

Poly(l-aspartic acid) derivative soluble in a volatile organic solvent for biomedical application

Nam Muk Oh
, Kyung Taek Oh
, Yu Seok Youn
, Eun Seong Lee

Department of Biomedical-Chemical Engineering

The Catholic University of Korea
Chung-Ang University
Sungkyunkwan University

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

13 Scopus citations

Abstract

In order to develop a novel functional poly(l-amino acid) that can dissolve in volatile organic solvents, we prepared poly[l-aspartic acid-g-(3-diethylaminopropyl)]-b-poly(ethylene glycol) [poly(l-Asp-g-DEAP)-b-PEG] via the conjugation of 3-diethylaminopropyl (DEAP) to carboxylate groups of poly(l-Asp) (M _n 4K)-b-PEG (M _n 2K). This poly(l-aspartic acid) derivative evidenced a relatively high solubility in volatile organic solvents such as dichloromethane, chloroform, and acetone. We fabricated a model nanostructure (i.e., polymeric micelle) using poly(l-Asp-g-DEAP)-b-PEG by the film rehydration method, which involves the simple removal of the volatile organic solvent (dichloromethane) used to dissolve polymer, reducing concerns about organic solvents remaining in a nano-sized particle. Interestingly, this micelle showed the pH-stimulated release of encapsulated model drug [i.e., doxorubicin (DOX)] due to the protonation of DEAP according to the pH of the solution. We expect that this poly(l-aspartic acid) derivative promises to provide pharmaceutical potential for constituting a new stimuli-sensitive drug carrier for various drug molecules.

Original language	English
Pages (from-to)	190-195
Number of pages	6
Journal	Colloids and Surfaces B: Biointerfaces
Volume	97
DOIs	https://doi.org/10.1016/j.colsurfb.2012.03.024
State	Published - 1 Sep 2012

Bibliographical note

Funding Information:
This work was financially supported by the Research Fund, 2012 of the Catholic University of Korea, by a grant of the Korean Health Technology R&D Project, Ministry of Health & Welfare (No. A111291 ), by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science, and Technology (No. 2011-0027373 and No. 2010-0007126 ), and by a Research Grant funded by the Gyeonggi Regional Research Center (GRRC).

Keywords

Diethylaminopropyl group
PH-sensitive polymer
Poly(l-aspartic acid) derivative
Volatile solvent

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10.1016/j.colsurfb.2012.03.024

Cite this

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title = "Poly(l-aspartic acid) derivative soluble in a volatile organic solvent for biomedical application",

abstract = "In order to develop a novel functional poly(l-amino acid) that can dissolve in volatile organic solvents, we prepared poly[l-aspartic acid-g-(3-diethylaminopropyl)]-b-poly(ethylene glycol) [poly(l-Asp-g-DEAP)-b-PEG] via the conjugation of 3-diethylaminopropyl (DEAP) to carboxylate groups of poly(l-Asp) (M n 4K)-b-PEG (M n 2K). This poly(l-aspartic acid) derivative evidenced a relatively high solubility in volatile organic solvents such as dichloromethane, chloroform, and acetone. We fabricated a model nanostructure (i.e., polymeric micelle) using poly(l-Asp-g-DEAP)-b-PEG by the film rehydration method, which involves the simple removal of the volatile organic solvent (dichloromethane) used to dissolve polymer, reducing concerns about organic solvents remaining in a nano-sized particle. Interestingly, this micelle showed the pH-stimulated release of encapsulated model drug [i.e., doxorubicin (DOX)] due to the protonation of DEAP according to the pH of the solution. We expect that this poly(l-aspartic acid) derivative promises to provide pharmaceutical potential for constituting a new stimuli-sensitive drug carrier for various drug molecules.",

keywords = "Diethylaminopropyl group, PH-sensitive polymer, Poly(l-aspartic acid) derivative, Volatile solvent",

author = "Oh, \{Nam Muk\} and Oh, \{Kyung Taek\} and Youn, \{Yu Seok\} and Lee, \{Eun Seong\}",

note = "Funding Information: This work was financially supported by the Research Fund, 2012 of the Catholic University of Korea, by a grant of the Korean Health Technology R\&D Project, Ministry of Health \& Welfare (No. A111291 ), by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science, and Technology (No. 2011-0027373 and No. 2010-0007126 ), and by a Research Grant funded by the Gyeonggi Regional Research Center (GRRC).",

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doi = "10.1016/j.colsurfb.2012.03.024",

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AU - Oh, Nam Muk

AU - Oh, Kyung Taek

AU - Youn, Yu Seok

AU - Lee, Eun Seong

N1 - Funding Information: This work was financially supported by the Research Fund, 2012 of the Catholic University of Korea, by a grant of the Korean Health Technology R&D Project, Ministry of Health & Welfare (No. A111291 ), by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science, and Technology (No. 2011-0027373 and No. 2010-0007126 ), and by a Research Grant funded by the Gyeonggi Regional Research Center (GRRC).

PY - 2012/9/1

Y1 - 2012/9/1

N2 - In order to develop a novel functional poly(l-amino acid) that can dissolve in volatile organic solvents, we prepared poly[l-aspartic acid-g-(3-diethylaminopropyl)]-b-poly(ethylene glycol) [poly(l-Asp-g-DEAP)-b-PEG] via the conjugation of 3-diethylaminopropyl (DEAP) to carboxylate groups of poly(l-Asp) (M n 4K)-b-PEG (M n 2K). This poly(l-aspartic acid) derivative evidenced a relatively high solubility in volatile organic solvents such as dichloromethane, chloroform, and acetone. We fabricated a model nanostructure (i.e., polymeric micelle) using poly(l-Asp-g-DEAP)-b-PEG by the film rehydration method, which involves the simple removal of the volatile organic solvent (dichloromethane) used to dissolve polymer, reducing concerns about organic solvents remaining in a nano-sized particle. Interestingly, this micelle showed the pH-stimulated release of encapsulated model drug [i.e., doxorubicin (DOX)] due to the protonation of DEAP according to the pH of the solution. We expect that this poly(l-aspartic acid) derivative promises to provide pharmaceutical potential for constituting a new stimuli-sensitive drug carrier for various drug molecules.

AB - In order to develop a novel functional poly(l-amino acid) that can dissolve in volatile organic solvents, we prepared poly[l-aspartic acid-g-(3-diethylaminopropyl)]-b-poly(ethylene glycol) [poly(l-Asp-g-DEAP)-b-PEG] via the conjugation of 3-diethylaminopropyl (DEAP) to carboxylate groups of poly(l-Asp) (M n 4K)-b-PEG (M n 2K). This poly(l-aspartic acid) derivative evidenced a relatively high solubility in volatile organic solvents such as dichloromethane, chloroform, and acetone. We fabricated a model nanostructure (i.e., polymeric micelle) using poly(l-Asp-g-DEAP)-b-PEG by the film rehydration method, which involves the simple removal of the volatile organic solvent (dichloromethane) used to dissolve polymer, reducing concerns about organic solvents remaining in a nano-sized particle. Interestingly, this micelle showed the pH-stimulated release of encapsulated model drug [i.e., doxorubicin (DOX)] due to the protonation of DEAP according to the pH of the solution. We expect that this poly(l-aspartic acid) derivative promises to provide pharmaceutical potential for constituting a new stimuli-sensitive drug carrier for various drug molecules.

KW - Diethylaminopropyl group

KW - PH-sensitive polymer

KW - Poly(l-aspartic acid) derivative

KW - Volatile solvent

UR - https://www.scopus.com/pages/publications/84861046005

U2 - 10.1016/j.colsurfb.2012.03.024

DO - 10.1016/j.colsurfb.2012.03.024

M3 - Article

C2 - 22609602

AN - SCOPUS:84861046005

SN - 0927-7765

VL - 97

SP - 190

EP - 195

JO - Colloids and Surfaces B: Biointerfaces

JF - Colloids and Surfaces B: Biointerfaces

ER -

Poly(l-aspartic acid) derivative soluble in a volatile organic solvent for biomedical application

Abstract

Bibliographical note

Keywords

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