Synthesis, circular dichroism, DNA cleavage and singlet oxygen photogeneration of 4-amidinophenyl porphyrins

Kai Wang; Chun T. Poon; Chun Y. Choi; Rick W K WONG; Daniel W J KWONG; Fa Q. Yu; Heng Zhang; Zao Y. Li

doi:10.1142/S108842461100435X

Synthesis, circular dichroism, DNA cleavage and singlet oxygen photogeneration of 4-amidinophenyl porphyrins

Kai Wang, Chun T. Poon, Chun Y. Choi, Rick W K WONG^*, Daniel W J KWONG, Fa Q. Yu, Heng Zhang, Zao Y. Li

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

21 Citations (Scopus)

Abstract

5,10,15,20-tetrakis(4-amidinophenyl)porphyrin (Por 1), its Zn complex (Por 2) and its conjugate with a tetraphenylporphyrin to form a bisporphyrin (Por 3) were prepared. The monomeric Por 1 and Por 2 showed both intercalative and external binding with DNA whereas only external DNA binding was seen in the bisporphyrin, Por 3 by circular dichroism and UV-vis. The DNA photocleavage activities of these porphyrins followed the order: Por 1 ∼ Por 2 > Por 3, which did not correlate with their measured ¹O₂ production rates. It suggests 4-amidinophenylporphyrins are promising new photodynamic therapeutic agents.

Original language	English
Pages (from-to)	85-92
Number of pages	8
Journal	Journal of Porphyrins and Phthalocyanines
Volume	16
Issue number	1
DOIs	https://doi.org/10.1142/S108842461100435X
Publication status	Published - Jan 2012

Scopus Subject Areas

General Chemistry

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amidinophenylporphyrin
binding mode
DNA cleavage
singlet oxygen

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10.1142/S108842461100435X

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title = "Synthesis, circular dichroism, DNA cleavage and singlet oxygen photogeneration of 4-amidinophenyl porphyrins",

abstract = "5,10,15,20-tetrakis(4-amidinophenyl)porphyrin (Por 1), its Zn complex (Por 2) and its conjugate with a tetraphenylporphyrin to form a bisporphyrin (Por 3) were prepared. The monomeric Por 1 and Por 2 showed both intercalative and external binding with DNA whereas only external DNA binding was seen in the bisporphyrin, Por 3 by circular dichroism and UV-vis. The DNA photocleavage activities of these porphyrins followed the order: Por 1 ∼ Por 2 > Por 3, which did not correlate with their measured 1O2 production rates. It suggests 4-amidinophenylporphyrins are promising new photodynamic therapeutic agents.",

keywords = "amidinophenylporphyrin, binding mode, DNA cleavage, singlet oxygen",

author = "Kai Wang and Poon, {Chun T.} and Choi, {Chun Y.} and WONG, {Rick W K} and KWONG, {Daniel W J} and Yu, {Fa Q.} and Heng Zhang and Li, {Zao Y.}",

note = "Funding Information: The authors are grateful for the financial supports of National Natural Science Foundation of China (Nos. 20902071, 20672082), Hong Kong Research Grants Council (No. HKBU 202407) and Open Funds of Key Laboratory for Green Chemical Process of Ministry of Education in China (No. RGCT201003).",

year = "2012",

month = jan,

doi = "10.1142/S108842461100435X",

language = "English",

volume = "16",

pages = "85--92",

journal = "Journal of Porphyrins and Phthalocyanines",

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publisher = "World Scientific Publishing Co. Pte Ltd",

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T1 - Synthesis, circular dichroism, DNA cleavage and singlet oxygen photogeneration of 4-amidinophenyl porphyrins

AU - Wang, Kai

AU - Poon, Chun T.

AU - Choi, Chun Y.

AU - WONG, Rick W K

AU - KWONG, Daniel W J

AU - Yu, Fa Q.

AU - Zhang, Heng

AU - Li, Zao Y.

N1 - Funding Information: The authors are grateful for the financial supports of National Natural Science Foundation of China (Nos. 20902071, 20672082), Hong Kong Research Grants Council (No. HKBU 202407) and Open Funds of Key Laboratory for Green Chemical Process of Ministry of Education in China (No. RGCT201003).

PY - 2012/1

Y1 - 2012/1

N2 - 5,10,15,20-tetrakis(4-amidinophenyl)porphyrin (Por 1), its Zn complex (Por 2) and its conjugate with a tetraphenylporphyrin to form a bisporphyrin (Por 3) were prepared. The monomeric Por 1 and Por 2 showed both intercalative and external binding with DNA whereas only external DNA binding was seen in the bisporphyrin, Por 3 by circular dichroism and UV-vis. The DNA photocleavage activities of these porphyrins followed the order: Por 1 ∼ Por 2 > Por 3, which did not correlate with their measured 1O2 production rates. It suggests 4-amidinophenylporphyrins are promising new photodynamic therapeutic agents.

AB - 5,10,15,20-tetrakis(4-amidinophenyl)porphyrin (Por 1), its Zn complex (Por 2) and its conjugate with a tetraphenylporphyrin to form a bisporphyrin (Por 3) were prepared. The monomeric Por 1 and Por 2 showed both intercalative and external binding with DNA whereas only external DNA binding was seen in the bisporphyrin, Por 3 by circular dichroism and UV-vis. The DNA photocleavage activities of these porphyrins followed the order: Por 1 ∼ Por 2 > Por 3, which did not correlate with their measured 1O2 production rates. It suggests 4-amidinophenylporphyrins are promising new photodynamic therapeutic agents.

KW - amidinophenylporphyrin

KW - binding mode

KW - DNA cleavage

KW - singlet oxygen

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U2 - 10.1142/S108842461100435X

DO - 10.1142/S108842461100435X

M3 - Journal article

AN - SCOPUS:84860489410

SN - 1088-4246

VL - 16

SP - 85

EP - 92

JO - Journal of Porphyrins and Phthalocyanines

JF - Journal of Porphyrins and Phthalocyanines

IS - 1

ER -

Synthesis, circular dichroism, DNA cleavage and singlet oxygen photogeneration of 4-amidinophenyl porphyrins

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