Synthesis of novel tetracationic phthalocyanines and investigation of their DNA-binding properties

Didem Evren; Ayfer Kalkan Burat; Ibrahim Özçeşmeci; B. Şebnem Sesalan

doi:10.1016/j.dyepig.2012.09.018

Synthesis of novel tetracationic phthalocyanines and investigation of their DNA-binding properties

Didem Evren, Ayfer Kalkan Burat^*, Ibrahim Özçeşmeci, B. Şebnem Sesalan

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

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

35 Citations (Scopus)

Abstract

The synthesis of novel, tetracationic zinc (1Q) and metal-free (2Q) phthalocyanines (Pcs) bearing 4-((7-(trifluoromethyl)quinolin-4-yl)oxy) units on the periphery have been reported. The new compounds were characterized by using elemental analysis, ¹H NMR, UV-vis and FT-IR spectroscopy and mass spectrometry. The binding properties of both 1Q and 2Q to CT-DNA are investigated in water by absorption and fluorescence spectroscopy. The quenching effect of all quaternized phthalocyanines (1Q and 2Q) on the fluorescence intensity of 4′,6-diamidino-2-phenylindoledihydrochloride (DAPI Gold)-DNA complex was determined. This study showed that the water-soluble quaternized zinc (1Q) and metal-free phthalocyanines (2Q) exhibit efficient DNA-binding activity.

Original language	English
Pages (from-to)	475-482
Number of pages	8
Journal	Dyes and Pigments
Volume	96
Issue number	2
DOIs	https://doi.org/10.1016/j.dyepig.2012.09.018
Publication status	Published - Feb 2013

Funding

This work was supported by TUBITAK (Project no: 110T800 ).

Funders	Funder number
TUBITAK	110T800

Keywords

Aggregation
DNA
Photodynamic therapy
Phthalocyanines
Quaternized
Water soluble

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10.1016/j.dyepig.2012.09.018

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title = "Synthesis of novel tetracationic phthalocyanines and investigation of their DNA-binding properties",

abstract = "The synthesis of novel, tetracationic zinc (1Q) and metal-free (2Q) phthalocyanines (Pcs) bearing 4-((7-(trifluoromethyl)quinolin-4-yl)oxy) units on the periphery have been reported. The new compounds were characterized by using elemental analysis, 1H NMR, UV-vis and FT-IR spectroscopy and mass spectrometry. The binding properties of both 1Q and 2Q to CT-DNA are investigated in water by absorption and fluorescence spectroscopy. The quenching effect of all quaternized phthalocyanines (1Q and 2Q) on the fluorescence intensity of 4′,6-diamidino-2-phenylindoledihydrochloride (DAPI Gold)-DNA complex was determined. This study showed that the water-soluble quaternized zinc (1Q) and metal-free phthalocyanines (2Q) exhibit efficient DNA-binding activity.",

keywords = "Aggregation, DNA, Photodynamic therapy, Phthalocyanines, Quaternized, Water soluble",

author = "Didem Evren and Burat, \{Ayfer Kalkan\} and Ibrahim {\"O}z{\c c}e{\c s}meci and Sesalan, \{B. {\c S}ebnem\}",

year = "2013",

month = feb,

doi = "10.1016/j.dyepig.2012.09.018",

language = "English",

volume = "96",

pages = "475--482",

journal = "Dyes and Pigments",

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publisher = "Elsevier B.V.",

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TY - JOUR

T1 - Synthesis of novel tetracationic phthalocyanines and investigation of their DNA-binding properties

AU - Evren, Didem

AU - Burat, Ayfer Kalkan

AU - Özçeşmeci, Ibrahim

AU - Sesalan, B. Şebnem

PY - 2013/2

Y1 - 2013/2

N2 - The synthesis of novel, tetracationic zinc (1Q) and metal-free (2Q) phthalocyanines (Pcs) bearing 4-((7-(trifluoromethyl)quinolin-4-yl)oxy) units on the periphery have been reported. The new compounds were characterized by using elemental analysis, 1H NMR, UV-vis and FT-IR spectroscopy and mass spectrometry. The binding properties of both 1Q and 2Q to CT-DNA are investigated in water by absorption and fluorescence spectroscopy. The quenching effect of all quaternized phthalocyanines (1Q and 2Q) on the fluorescence intensity of 4′,6-diamidino-2-phenylindoledihydrochloride (DAPI Gold)-DNA complex was determined. This study showed that the water-soluble quaternized zinc (1Q) and metal-free phthalocyanines (2Q) exhibit efficient DNA-binding activity.

AB - The synthesis of novel, tetracationic zinc (1Q) and metal-free (2Q) phthalocyanines (Pcs) bearing 4-((7-(trifluoromethyl)quinolin-4-yl)oxy) units on the periphery have been reported. The new compounds were characterized by using elemental analysis, 1H NMR, UV-vis and FT-IR spectroscopy and mass spectrometry. The binding properties of both 1Q and 2Q to CT-DNA are investigated in water by absorption and fluorescence spectroscopy. The quenching effect of all quaternized phthalocyanines (1Q and 2Q) on the fluorescence intensity of 4′,6-diamidino-2-phenylindoledihydrochloride (DAPI Gold)-DNA complex was determined. This study showed that the water-soluble quaternized zinc (1Q) and metal-free phthalocyanines (2Q) exhibit efficient DNA-binding activity.

KW - Aggregation

KW - DNA

KW - Photodynamic therapy

KW - Phthalocyanines

KW - Quaternized

KW - Water soluble

UR - https://www.scopus.com/pages/publications/84868598355

U2 - 10.1016/j.dyepig.2012.09.018

DO - 10.1016/j.dyepig.2012.09.018

M3 - Article

AN - SCOPUS:84868598355

SN - 0143-7208

VL - 96

SP - 475

EP - 482

JO - Dyes and Pigments

JF - Dyes and Pigments

IS - 2

ER -

Synthesis of novel tetracationic phthalocyanines and investigation of their DNA-binding properties

Abstract

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Keywords

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