Modelling the behavior of 5-aminolevulinic acid and its alkyl esters in a lipid bilayer

Edvin Erdtman; Daniel J.V.A. dos Santos; Lennart Löfgren; Leif A. Eriksson

doi:10.1016/j.cplett.2008.08.021

Modelling the behavior of 5-aminolevulinic acid and its alkyl esters in a lipid bilayer

Edvin Erdtman, Daniel J.V.A. dos Santos, Lennart Löfgren, Leif A. Eriksson

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

18 Citations (Scopus)

Abstract

5-Aminolevulinic acid (5ALA) and ester derivates thereof are used as prodrugs in photodynamic therapy (PDT). The behavior of 5ALA and three esters of 5ALA in a DPPC lipid bilayer is investigated. In particular, the methyl ester displays a very different free energy profile, where the highest barrier is located in the region with highest lipid density, while the others have their peak in the middle of the membrane, and also displays a considerably lower permeability coefficient than neutral 5ALA and the ethyl ester. The zwitterion of 5ALA has the highest permeability constant, but a significant free energy minimum in the polar head-group region renders an accumulation in this region.

Original language	English
Pages (from-to)	178-182
Number of pages	5
Journal	Chemical Physics Letters
Volume	463
Issue number	1-3
DOIs	https://doi.org/10.1016/j.cplett.2008.08.021
Publication status	Published - 22 Sept 2008
Externally published	Yes

Funding

The faculty of Science and Technology at Örebro University, and the Swedish Science Research Council (VR) are gratefully acknowledged for financial support.

Funders	Funder number
Science and Technology at Örebro University
Vetenskapsrådet

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10.1016/j.cplett.2008.08.021

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abstract = "5-Aminolevulinic acid (5ALA) and ester derivates thereof are used as prodrugs in photodynamic therapy (PDT). The behavior of 5ALA and three esters of 5ALA in a DPPC lipid bilayer is investigated. In particular, the methyl ester displays a very different free energy profile, where the highest barrier is located in the region with highest lipid density, while the others have their peak in the middle of the membrane, and also displays a considerably lower permeability coefficient than neutral 5ALA and the ethyl ester. The zwitterion of 5ALA has the highest permeability constant, but a significant free energy minimum in the polar head-group region renders an accumulation in this region.",

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AU - Erdtman, Edvin

AU - dos Santos, Daniel J.V.A.

AU - Löfgren, Lennart

AU - Eriksson, Leif A.

PY - 2008/9/22

Y1 - 2008/9/22

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AB - 5-Aminolevulinic acid (5ALA) and ester derivates thereof are used as prodrugs in photodynamic therapy (PDT). The behavior of 5ALA and three esters of 5ALA in a DPPC lipid bilayer is investigated. In particular, the methyl ester displays a very different free energy profile, where the highest barrier is located in the region with highest lipid density, while the others have their peak in the middle of the membrane, and also displays a considerably lower permeability coefficient than neutral 5ALA and the ethyl ester. The zwitterion of 5ALA has the highest permeability constant, but a significant free energy minimum in the polar head-group region renders an accumulation in this region.

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JO - Chemical Physics Letters

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ER -

Modelling the behavior of 5-aminolevulinic acid and its alkyl esters in a lipid bilayer

Abstract

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