Synthesis of PHB-based carrier for drug delivery systems with pH-controlled release

Michał Michalak; Adam A. Marek; Jan Zawadiak; Michał Kawalec; Piotr Kurcok

doi:10.1016/j.eurpolymj.2013.09.021

Synthesis of PHB-based carrier for drug delivery systems with pH-controlled release

Michał Michalak
, Adam A. Marek
, Jan Zawadiak
, Michał Kawalec
, Piotr Kurcok

Department of Chemical Organic Technology and Petrochemistry (RCH/RCH5)

Polish Academy of Sciences

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

64 Citations (Scopus)

Abstract

Synthetic route to prepare model PHB-amine conjugate containing hydrolysable imine bond is reported. Short-chain PHB crotonate is converted into PHB glyoxylate via clean and efficient ozonolysis followed by reductive decomposition of peroxidic products with dimethylsulfide. Aldehyde- functionalized PHB is obtained quantitatively without polymer backbone degradation while PHB-amine conjugate is synthesized with very high yield. Release properties of such-prepared conjugate is confirmed in hydrolysis experiment revealing pH-dependent kinetics of amine release. Simplicity of the protocol in conjunction with unique properties of PHB carrier are believed to be powerful tool for development of novel drug conjugates.

Original language	English
Pages (from-to)	4149-4156
Number of pages	8
Journal	European Polymer Journal
Volume	49
Issue number	12
DOIs	https://doi.org/10.1016/j.eurpolymj.2013.09.021
Publication status	Published - Dec 2013

Keywords

Controlled release
Functional PHB
Ozonolysis
PHB-based carrier

ASJC Scopus subject areas

General Physics and Astronomy
Organic Chemistry
Polymers and Plastics
Materials Chemistry

Access to Document

10.1016/j.eurpolymj.2013.09.021

Cite this

@article{557f790586a146859a3a9aaeacb98bef,

title = "Synthesis of PHB-based carrier for drug delivery systems with pH-controlled release",

abstract = "Synthetic route to prepare model PHB-amine conjugate containing hydrolysable imine bond is reported. Short-chain PHB crotonate is converted into PHB glyoxylate via clean and efficient ozonolysis followed by reductive decomposition of peroxidic products with dimethylsulfide. Aldehyde- functionalized PHB is obtained quantitatively without polymer backbone degradation while PHB-amine conjugate is synthesized with very high yield. Release properties of such-prepared conjugate is confirmed in hydrolysis experiment revealing pH-dependent kinetics of amine release. Simplicity of the protocol in conjunction with unique properties of PHB carrier are believed to be powerful tool for development of novel drug conjugates.",

keywords = "Controlled release, Functional PHB, Ozonolysis, PHB-based carrier",

author = "Micha{\l} Michalak and Marek, \{Adam A.\} and Jan Zawadiak and Micha{\l} Kawalec and Piotr Kurcok",

year = "2013",

month = dec,

doi = "10.1016/j.eurpolymj.2013.09.021",

language = "English",

volume = "49",

pages = "4149--4156",

journal = "European Polymer Journal",

issn = "0014-3057",

publisher = "Elsevier Ltd.",

number = "12",

}

TY - JOUR

T1 - Synthesis of PHB-based carrier for drug delivery systems with pH-controlled release

AU - Michalak, Michał

AU - Marek, Adam A.

AU - Zawadiak, Jan

AU - Kawalec, Michał

AU - Kurcok, Piotr

PY - 2013/12

Y1 - 2013/12

N2 - Synthetic route to prepare model PHB-amine conjugate containing hydrolysable imine bond is reported. Short-chain PHB crotonate is converted into PHB glyoxylate via clean and efficient ozonolysis followed by reductive decomposition of peroxidic products with dimethylsulfide. Aldehyde- functionalized PHB is obtained quantitatively without polymer backbone degradation while PHB-amine conjugate is synthesized with very high yield. Release properties of such-prepared conjugate is confirmed in hydrolysis experiment revealing pH-dependent kinetics of amine release. Simplicity of the protocol in conjunction with unique properties of PHB carrier are believed to be powerful tool for development of novel drug conjugates.

AB - Synthetic route to prepare model PHB-amine conjugate containing hydrolysable imine bond is reported. Short-chain PHB crotonate is converted into PHB glyoxylate via clean and efficient ozonolysis followed by reductive decomposition of peroxidic products with dimethylsulfide. Aldehyde- functionalized PHB is obtained quantitatively without polymer backbone degradation while PHB-amine conjugate is synthesized with very high yield. Release properties of such-prepared conjugate is confirmed in hydrolysis experiment revealing pH-dependent kinetics of amine release. Simplicity of the protocol in conjunction with unique properties of PHB carrier are believed to be powerful tool for development of novel drug conjugates.

KW - Controlled release

KW - Functional PHB

KW - Ozonolysis

KW - PHB-based carrier

UR - https://www.scopus.com/pages/publications/84888309798

U2 - 10.1016/j.eurpolymj.2013.09.021

DO - 10.1016/j.eurpolymj.2013.09.021

M3 - Article

AN - SCOPUS:84888309798

SN - 0014-3057

VL - 49

SP - 4149

EP - 4156

JO - European Polymer Journal

JF - European Polymer Journal

IS - 12

ER -

Synthesis of PHB-based carrier for drug delivery systems with pH-controlled release

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this