Conjugation of the photosensitizer Chlorin e6 to pluronic F127 for enhanced cellular internalization for photodynamic therapy

Hyung Park; Kun Na

doi:10.1016/j.biomaterials.2013.05.070

Conjugation of the photosensitizer Chlorin e6 to pluronic F127 for enhanced cellular internalization for photodynamic therapy

Hyung Park
, Kun Na

The Catholic University of Korea

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

150 Scopus citations

Abstract

To improve the cellular internalization and tumor-specific targeting efficiency of a photosensitizer, Chlorin e6 (Ce6), was conjugated to Pluronic F127^® (PF127) by esterification between the carboxylic groups of Ce6 and the two hydroxyl groups of PF127 (PCe6). After conjugation, two different PCe6 conjugates, PF127/Ce6 (PCe6-1) and Ce6/PF127/Ce6 (PCe6-2), were obtained and separated by hydrophobic interaction chromatography. In this study, PCe6-1 was employed because it has good solubility in aqueous media. The singlet oxygen generation (SOG) efficiency and fluorescence activity of PCe6-1 in aqueous media dramatically increased compared to free Ce6. Moreover, confocal imaging and fluorescence-activated cell sorting (FACS) analysis confirmed its enhanced internalization rate in mouse colon tumor (CT-26) cells. After light irradiation, the cellular phototoxicity of PCe6-1 against CT-26 was approximately 3 times higher than that of free Ce6 invitro. Furthermore, PCe6-1 exhibited enhanced tumor-specific distribution and tumor growth inhibition after intravenous injection into tumor-bearing mice. These results suggest that PCe6-1 is a good candidate as a photosensitizer due to its high cellular internalization rate and tumor targeting efficiency.

Original language	English
Pages (from-to)	6992-7000
Number of pages	9
Journal	Biomaterials
Volume	34
Issue number	28
DOIs	https://doi.org/10.1016/j.biomaterials.2013.05.070
State	Published - Sep 2013

Bibliographical note

Funding Information:
We acknowledge the financial support of the Korea Ministry of Education, Science and Technology through Strategic Research ( 2011-0028726 ).

Keywords

Chlorin e6
Internalization rate
Photosensitizer
Pluronic F127
Site-specific distribution

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10.1016/j.biomaterials.2013.05.070

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title = "Conjugation of the photosensitizer Chlorin e6 to pluronic F127 for enhanced cellular internalization for photodynamic therapy",

abstract = "To improve the cellular internalization and tumor-specific targeting efficiency of a photosensitizer, Chlorin e6 (Ce6), was conjugated to Pluronic F127{\textregistered} (PF127) by esterification between the carboxylic groups of Ce6 and the two hydroxyl groups of PF127 (PCe6). After conjugation, two different PCe6 conjugates, PF127/Ce6 (PCe6-1) and Ce6/PF127/Ce6 (PCe6-2), were obtained and separated by hydrophobic interaction chromatography. In this study, PCe6-1 was employed because it has good solubility in aqueous media. The singlet oxygen generation (SOG) efficiency and fluorescence activity of PCe6-1 in aqueous media dramatically increased compared to free Ce6. Moreover, confocal imaging and fluorescence-activated cell sorting (FACS) analysis confirmed its enhanced internalization rate in mouse colon tumor (CT-26) cells. After light irradiation, the cellular phototoxicity of PCe6-1 against CT-26 was approximately 3 times higher than that of free Ce6 invitro. Furthermore, PCe6-1 exhibited enhanced tumor-specific distribution and tumor growth inhibition after intravenous injection into tumor-bearing mice. These results suggest that PCe6-1 is a good candidate as a photosensitizer due to its high cellular internalization rate and tumor targeting efficiency.",

keywords = "Chlorin e6, Internalization rate, Photosensitizer, Pluronic F127, Site-specific distribution",

author = "Hyung Park and Kun Na",

note = "Funding Information: We acknowledge the financial support of the Korea Ministry of Education, Science and Technology through Strategic Research ( 2011-0028726 ). ",

year = "2013",

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doi = "10.1016/j.biomaterials.2013.05.070",

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T1 - Conjugation of the photosensitizer Chlorin e6 to pluronic F127 for enhanced cellular internalization for photodynamic therapy

AU - Park, Hyung

AU - Na, Kun

N1 - Funding Information: We acknowledge the financial support of the Korea Ministry of Education, Science and Technology through Strategic Research ( 2011-0028726 ).

PY - 2013/9

Y1 - 2013/9

N2 - To improve the cellular internalization and tumor-specific targeting efficiency of a photosensitizer, Chlorin e6 (Ce6), was conjugated to Pluronic F127® (PF127) by esterification between the carboxylic groups of Ce6 and the two hydroxyl groups of PF127 (PCe6). After conjugation, two different PCe6 conjugates, PF127/Ce6 (PCe6-1) and Ce6/PF127/Ce6 (PCe6-2), were obtained and separated by hydrophobic interaction chromatography. In this study, PCe6-1 was employed because it has good solubility in aqueous media. The singlet oxygen generation (SOG) efficiency and fluorescence activity of PCe6-1 in aqueous media dramatically increased compared to free Ce6. Moreover, confocal imaging and fluorescence-activated cell sorting (FACS) analysis confirmed its enhanced internalization rate in mouse colon tumor (CT-26) cells. After light irradiation, the cellular phototoxicity of PCe6-1 against CT-26 was approximately 3 times higher than that of free Ce6 invitro. Furthermore, PCe6-1 exhibited enhanced tumor-specific distribution and tumor growth inhibition after intravenous injection into tumor-bearing mice. These results suggest that PCe6-1 is a good candidate as a photosensitizer due to its high cellular internalization rate and tumor targeting efficiency.

AB - To improve the cellular internalization and tumor-specific targeting efficiency of a photosensitizer, Chlorin e6 (Ce6), was conjugated to Pluronic F127® (PF127) by esterification between the carboxylic groups of Ce6 and the two hydroxyl groups of PF127 (PCe6). After conjugation, two different PCe6 conjugates, PF127/Ce6 (PCe6-1) and Ce6/PF127/Ce6 (PCe6-2), were obtained and separated by hydrophobic interaction chromatography. In this study, PCe6-1 was employed because it has good solubility in aqueous media. The singlet oxygen generation (SOG) efficiency and fluorescence activity of PCe6-1 in aqueous media dramatically increased compared to free Ce6. Moreover, confocal imaging and fluorescence-activated cell sorting (FACS) analysis confirmed its enhanced internalization rate in mouse colon tumor (CT-26) cells. After light irradiation, the cellular phototoxicity of PCe6-1 against CT-26 was approximately 3 times higher than that of free Ce6 invitro. Furthermore, PCe6-1 exhibited enhanced tumor-specific distribution and tumor growth inhibition after intravenous injection into tumor-bearing mice. These results suggest that PCe6-1 is a good candidate as a photosensitizer due to its high cellular internalization rate and tumor targeting efficiency.

KW - Chlorin e6

KW - Internalization rate

KW - Photosensitizer

KW - Pluronic F127

KW - Site-specific distribution

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DO - 10.1016/j.biomaterials.2013.05.070

M3 - Article

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SN - 0142-9612

VL - 34

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JO - Biomaterials

JF - Biomaterials

IS - 28

ER -

Conjugation of the photosensitizer Chlorin e6 to pluronic F127 for enhanced cellular internalization for photodynamic therapy

Abstract

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Keywords

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