N-Methylpyridylporphyrin tailed with folate conjugate as a potential lysosomal-targeted photosensitizer: Synthesis, DNA interaction, singlet oxygen and subcellular localization

2019 ◽  
Vol 23 (06) ◽  
pp. 679-684
Author(s):  
Yi-Mei Zhao ◽  
Qian-Qian Lu ◽  
Si Yao ◽  
Hui-Fang Su ◽  
Hong-Jian Liu ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Fluorescence Spectra ◽  
Binding Constants ◽  
Binding Mode ◽  
Dna Interaction ◽  
H Nmr ◽  
Calf Thymus ◽  
Folate Conjugate ◽  
Tumor Drugs

In recent years, great interest has been focused on the use of photosensitizers (PS) for photodynamic therapy (PDT) as safe and effective anti-tumor drugs. As a good lysosomal-targeted drug, folic acid (FA) is highly interesting as well. [Formula: see text]-methylpyridylporphyrin tailed with folate conjugate (Me-Por-FA) was newly designed and synthesized and the structure was confirmed by UV-vis, IR, 1H NMR, MS and elemental analysis. The interaction of this porphyrin with calf thymus DNA was the intercalative binding mode, which was confirmed by ultraviolet and fluorescence spectra, and the binding constants [Formula: see text] was 6.24 × 104 L/mol. The singlet oxygen (1O[Formula: see text] generated by Me-Por-FA was determined by 1, 3-diphenylisobenzofuran (DPBF) method using tetrapyridylporphyrin (H[Formula: see text]TMPyP) as a comparison with the following order: H2TMPyP > Me-Por-FA. Stained with LysoTracker[Formula: see text] Green DND-26, Me-Por-FA was mainly distributed over the lysosomes during 4 h, but H[Formula: see text]TMPyP was not. This suggests that Me-Por-FA could be developed as a targeted photosensitizer for precise photodynamic therapy.

New peripherally substituted lutetium mono and bis phthalocyanines: Synthesis and comparative photophysical and photochemical properties

2019 ◽  
Vol 23 (11n12) ◽  
pp. 1542-1550
Author(s):  
Nagihan Kocaağa ◽  
Öznur Dülger Kutlu ◽  
Ali Erdoğmuş
Keyword(s):  
Mass Spectrometry ◽  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Photophysical Properties ◽  
Quantum Yields ◽  
Synthesis And Characterization ◽  
Type Ii ◽  
H Nmr ◽  
Photochemical Properties

In this study, the synthesis and characterization of mono-(phthalocyaninato) lutetium(III) (1-Cl and 1-F) [Lu[Formula: see text](AcO)(Pc)] (Pc [Formula: see text] phthalocyaninato, AcO [Formula: see text] acetate) and bis-(phthalocyaninato) lutetium(III) (2-Cl and 2-Br) [Lu[Formula: see text]Pc[Formula: see text]] bearing halogenated (F, Cl and Br) phenoxy–phenoxy groups are described and verified by IR, [Formula: see text]H-NMR, UV-vis and mass spectrometry. Photochemical and photophysical properties of 1-F, 1-Cl 2-Cl and 2-Br in DMSO are also presented. A comparison between photophysical and photochemical parameters of mono and bis derivatives showed that mono phthalocyanines are better photosensitizers than bis phthalocyanines. Photophysical and photochemical properties of phthalocyanines are very useful for photodynamic therapy applications. Singlet oxygen quantum yields [Formula: see text] give an indication of the potential of the complexes as photosensitizers in photodynamic therapy applications. The chloro, fluoro, bromo-phenoxy–phenoxy substituted mono-(phthalocyaninato) lutetium(III) complexes (1-Cl and 1-F) gave good singlet oxygen quantum yields (from 0.86 to 0.80) in DMSO. Thus, these complexes show potential as Type II photosensitizers for PDT of cancer.

scholarly journals DNA Interaction Studies of a New Platinum(II) Complex Containing Different Aromatic Dinitrogen Ligands

2011 ◽  
Vol 2011 ◽  
pp. 1-8 ◽  
Author(s):  
Nahid Shahabadi ◽  
Somaye Mohammadi ◽  
Robabeh Alizadeh
Keyword(s):  
Absorption Band ◽  
Bathochromic Shift ◽  
Binding Mode ◽  
Dna Interaction ◽  
Quenching Mechanism ◽  
Binding Interaction ◽  
Fluorescence Studies ◽  
Cyclic Voltametry ◽  
Calf Thymus ◽  
Ct Dna

A new mononuclear Pt(II) complex, [Pt(DMP)(DIP)]Cl2.H2O, in which DMP is 4,4-dimethyl-2,2-bipyridine and DIP is 4,7-diphenyl-1,10-phenantroline, has been synthesized and characterized by physicochemical and spectroscopic methods. The binding interaction of this complex with calf thymus DNA (CT-DNA) was investigated using fluorimetry, spectrophotometry, circular dichroism, viscosimetry and cyclic voltametry (CV). UV-VIS spectrum showed 4 nm bathochromic shift of the absorption band at 280 nm along with significant hypochromicity for the absorption band of the complex. The intrnisic binding constant is more in keeping with intercalators and suggests this binding mode. The viscosity measurements showed that the complex-DNA interaction can be hydrophobic and confirm intercalation. Moreover, the complex induced detectable changes in the CD spectrum of CT-DNA. The fluorescence studies revealed that the probable quenching mechanism of fluorescence of the complex by CT-DNA is static quenching. The thermodynamic parameters ( and ) showed that main interaction with hydrogenic forces occurred that is intercalation mode. Also, CV results confirm this mode because, with increasing the CT-DNA concentration, shift to higher potential was observed.

scholarly journals DNA binding and photo-induced DNA cleavage activity of Elsinochrome A in visible light

2011 ◽  
Vol 26 (4-5) ◽  
pp. 289-296
Author(s):  
Fei Ma ◽  
Jing Tang ◽  
Chao Yang ◽  
Yu-Ying Feng ◽  
Shao-Hua Wei ◽  
...  
Keyword(s):  
Visible Light ◽  
Dna Cleavage ◽  
Fluorescence Spectra ◽  
Binding Mode ◽  
Strong Force ◽  
Dna Cleavage Activity ◽  
Calf Thymus ◽  
Electrostatic Binding ◽  
Ct Dna ◽  
Elsinochrome A

The interaction of Elsinochrome A (EA) with calf thymus DNA (CT-DNA) has been investigated by UV-vis spectra and fluorescence spectra. The results show that EA can bind with CT-DNA and binding sites are destroyed after irradiation by visible light, which indicates that EA is a promising candidate for photodynamic therapy. In addition, the binding mechanism is studied using fluorescence quenching test and ethidium bromide (EB) replace assay experiments. The results suggest that EA and CT-DNA are binding with a strong force and the major binding mode of EA with DNA could be the electrostatic binding.

Bis-indole substituted phthalocyanines: Photophysical and photochemical properties

2020 ◽  
Vol 25 (01) ◽  
pp. 66-74
Author(s):  
Kevser Harmandar ◽  
Esra N. Kaya ◽  
Mehmet F. Saglam ◽  
Ibrahim F. Sengul ◽  
Devrim Atilla
Keyword(s):  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Spectral Data ◽  
Quantum Yields ◽  
Oxygen Generation ◽  
Fluorescence Quantum Yields ◽  
H Nmr ◽  
Singlet Oxygen Generation ◽  
Photochemical Properties ◽  
C Nmr

Tetra substituted peripheral and non-peripheral Zn(II) phthalocyanines were successfully synthesized employing 4-(bis(3-methyl-1H-indol-2-yl)methyl)phenol as a starting material. The structure of these synthesized compounds was confirmed using 1H NMR, [Formula: see text]C NMR, infrared (IR), UV-vis, and MALDI-TOF spectral data. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation) properties of all synthesized peripheral and non-peripheral compounds were investigated in order to determine the potential of these compounds for application in photodynamic therapy.

scholarly journals Study on Interaction of Cationic Porphyrazine with Synthetic Polynucleotides

2013 ◽  
Vol 36 (5-6) ◽  
pp. 125-132 ◽  
Author(s):  
Hamid Dezhampanah ◽  
Soghra Fyzolahjani
Keyword(s):  
Electrostatic Interactions ◽  
Fluorescence Emission ◽  
Binding Constants ◽  
Binding Mode ◽  
Calf Thymus ◽  
Quenching Process ◽  
Enthalpy And Entropy Changes ◽  
Enthalpy And Entropy ◽  
Hoff Equation ◽  
Groove Binding Mode

Interactions of cationic tetrakis (N, N′, N″, N‴- tetramethyltetra-3, 4-pyridinoporphyrazinatozinc (II) (Zn (tmtppa)) with synthetic polynucleotides, poly (G-C) and poly (A-T), and calf thymus DNA have been characterized in 7.5 mM phosphate buffer of pH 7.2 by UV-Vis absorption and fluorescence spectroscopy. The appearance of hypochromicity more than 30% in UV-Vis spectra of porphyrazine due to interaction of both poly (G-C) and poly (A-T) indicates interaction similar to that of porphyrazine with DNA.The binding constants were determined from the changes in the Q-band maximum of the porphyrazine spectra at various poly (G-C) and DNA concentrations. The values of K were 2.5 × 106M−1, 2.5 × 106M−1and 2.5 × 105M−1for poly (G-C), poly (A-T) and DNA, respectively, at 25°C. The thermodynamic parameters (ΔG°, ΔH°, ΔS°) were calculated using the van't Hoff equation at various temperatures. The enthalpy and entropy changes were determined to be 41.14 kJ mol−1and 260.50 J mol−1·K−1for poly (G-C) and 53.59 kJ mol−1and 285.46 J mol−1·K−1for DNA at 25°C. The positive and large values of the entropy and enthalpy suggest that both hydrophobic and electrostatic interactions may play an important role in the stabilization of the complex formation. The binding of polynucleotides to porphyrazine quenches fluorescence emission of ethidium bromide (EB), and the quenching process obeys linear Stern-Volmer relationship. The results reviled groove-binding mode of porphyrazine for both AT- and GC-rich polynucleotides of DNA.

scholarly journals Interaction of an abiraterone with calf thymus DNA: Investigation with spectroscopic technique and modeling studies

2019 ◽  
Author(s):  
Tanveer A. Wani ◽  
Nawaf Alsaif ◽  
Ahmed H. Bakheit ◽  
Seema Zargar ◽  
Abdurrahman A. Al-Mehizia ◽  
...  
Keyword(s):  
Binding Energy ◽  
Experimental Studies ◽  
Binding Constants ◽  
Binding Mode ◽  
Docking Studies ◽  
Spectroscopic Technique ◽  
Calf Thymus Dna ◽  
Quenching Effect ◽  
Mechanisms Of Toxicity ◽  
Calf Thymus

AbstractBinding of toxic ligands to DNA could result in undesirable biological processes, such as carcinogenesis or mutagenesis. Binding mode of Abiraterone (ABR), a steroid drug and ctDNA(calf thymus DNA was investigated in this study using fluorescence and ultraviolet–visible spectroscopy. The probable prediction of binding and the type of interaction forces involved in the arrangement between ABR and ctDNA were explored through spectroscopic and molecular docking studies. The results indicated the binding of ABR to ctDNA in the minor groove. The binding constants were in the range of 1.35 × 106 – 0.36× 106 L mol-1 at the studied temperatures. Fluorescence and spectrophotometric data suggested static quenching between ctDNA and ABR The endothermic values of thermodynamic parameters ΔH = -82.8 kJ mol−1; ΔS = - 161 J mol−1 K−1 suggested that hydrogen bonding is the main force involved in binding ctDNA and ABR. In experimental studies the free binding energy at 298K was −34.9 kJ mol−1 with the relative binding energy ≈ −29.65 kJ mol−1 of docked structure. The Ksv obtained for ABR-KI was similar to that for ABR-ctDNA -KI demonstrating no protection by ctDNA against quenching effect of KI. Thus, suggesting involvement of groove binding between ABR and ctDNA. No change in the fluorescence intensity of ABR-ctDNA was observed in presence of NaCl. Thus, ruling out the involvement of electrostatic interaction. These studies could serve as new insights in understanding the mechanisms of toxicity, resistance and side effects of ABR.

scholarly journals Synthesis, DNA interaction and antibacterial activities of La(III) and Gd(III) complexes of Schiff base derived from o-vanillin and lysine

2009 ◽  
Vol 7 (1) ◽  
pp. 105-110 ◽  
Author(s):  
Jian-Ping Cheng ◽  
Qiu-Yue Lin ◽  
Hu Rui-Ding ◽  
Wen-Zhong Zhu ◽  
Hua-Qiong Li ◽  
...  
Keyword(s):  
Schiff Base ◽  
Binding Mode ◽  
Dna Interaction ◽  
Antibacterial Activities ◽  
Azomethine Nitrogen ◽  
Moderate Activity ◽  
Phenolic Oxygen ◽  
Calf Thymus ◽  
Ct Dna ◽  
Remarkable Reduction

AbstractTwo novel complexes, [La(HL)(H2O)2NO3] · NO3 · H2O and [Gd(HL)(H2O)2NO3] · NO3 · H2O, where HL is a Schiff base derived from o-vanillin and lysine, have been synthesized and characterized by elemental analysis, conductivity measurements, IR, 1H NMR and thermogravimetric analyses (TGA). The Schiff base ligand behaves as a tetradentate, coordinating through azomethine nitrogen, phenolic oxygen and two carboxylic oxygen atoms. The interaction of these complexes with calf thymus DNA (CT-DNA) was also investigated by spectrometric titration and viscometric measurements. The faint hypochromism of the complexes in the absorption spectra, the remarkable reduction of fluorescence intensity of ethidium bromide (EB) bound DNA, together with a small decrease in the viscosity of the DNA suggest that a partial intercalation may be the preferred binding mode between these two complexes and DNA. The antibacterial activity testing revealed that the complexes and their precursor Schiff base show a weak to moderate activity against Bacillus subtilis, Staphylococcus aureus and Escherichia coli.

scholarly journals Synthesis, Characterization, DNA Interaction, and Antitumor Activities of La (III) Complex with Schiff Base Ligand Derived from Kaempferol and Diethylenetriamine

2014 ◽  
Vol 2014 ◽  
pp. 1-9 ◽  
Author(s):  
Qin Wang ◽  
Yu Huang ◽  
Jin-Sheng Zhang ◽  
Xin-Bin Yang
Keyword(s):  
Schiff Base ◽  
Schiff Base Ligand ◽  
Free Ligand ◽  
Binding Constants ◽  
Dna Interaction ◽  
Molar Conductance ◽  
Cytotoxic Activities ◽  
H Nmr ◽  
Intercalative Mode ◽  
Fluorescence Quenching Mechanism

A novel La (III) complex, [LaL(H2O)3]NO3·3H2O, with Schiff base ligandLderived from kaempferol and diethylenetriamine, has been synthesized and characterized by elemental analysis, IR, UV-visible,1H NMR, thermogravimetric analysis, and molar conductance measurements. The fluorescence spectra, circular dichroism spectra, and viscosity measurements and gel electrophoresis experiments indicated that the ligandLand La (III) complex could bind to CT-DNA presumably via intercalative mode and the La (III) complex showed a stronger ability to bind and cleave DNA than the ligandLalone. The binding constants (Kb) were evaluated from fluorescence data and the values ranged from 0.454 to 0.659 × 105L mol−1and 1.71 to 17.3 × 105L mol−1for the ligandLand La (III) complex, respectively, in the temperature range of 298–310 K. It was also found that the fluorescence quenching mechanism of EB-DNA by ligandLand La (III) complex was a static quenching process. In comparison to free ligandL, La (III) complex exhibited enhanced cytotoxic activities against tested tumor cell lines HL-60 and HepG-2, which may correlate with the enhanced DNA binding and cleaving abilities of the La (III) complex.

Structural analysis of DNA interaction with retinol and retinoic acid

2010 ◽  
Vol 88 (3) ◽  
pp. 469-477 ◽  
Author(s):  
J. S. Mandeville ◽  
C. N. N’soukpoé-Kossi ◽  
J. F. Neault ◽  
H. A. Tajmir-Riahi
Keyword(s):  
Retinoic Acid ◽  
Structural Analysis ◽  
Fruits And Vegetables ◽  
Hydrophobic Interactions ◽  
Binding Constants ◽  
Beta Carotene ◽  
Binding Mode ◽  
Dna Interaction ◽  
Base Pairs ◽  
Relevant Role

Dietary constituents of fresh fruits and vegetables may play a relevant role in DNA adduct formation by inhibiting enzymatic activities. Studies have shown the important role of antioxidant vitamins A, C, and E in the protection against cancer and cardiovascular diseases. The antioxidant activity of vitamin A and beta-carotene may consist of scavenging oxygen radicals and preventing DNA damage. This study was designed to examine the interaction of calf-thymus DNA with retinol and retinoic acid in aqueous solution at physiological conditions using a constant DNA concentration and various retinoid contents. Fourier transform infrared (FTIR), circular dichroism (CD), and fluorescence spectroscopic methods were used to determine retinoid binding mode, the binding constant, and the effects of retinol and retinoic acid complexation on DNA conformation and aggregation. Structural analysis showed that retinol and retinoic acid bind DNA via G-C and A-T base pairs and the backbone phosphate groups with overall binding constants of Kret = 3.0 (±0.50) × 103 (mol·L–1)–1 and Kretac = 1.0 (±0.20) × 104 (mol·L–1)–1. The number of bound retinoids per DNA were 0.84 for retinol and 1.3 for retinoic acid. Hydrophobic interactions were also observed at high retinol and retinoic acid contents. At a high retinoid concentration, major DNA aggregation occurred, while DNA remained in the B-family structure.

scholarly journals DNA Binding of Some Chiral Metallointercalators Derived From 9,10-Phenanthrenediamine

1998 ◽  
Vol 5 (4) ◽  
pp. 225-231 ◽  
Author(s):  
Susan F. Murphy-Poulton ◽  
Robert S. Vagg ◽  
Kymberley A. Vickery ◽  
Peter A. Williams
Keyword(s):  
Nucleic Acid ◽  
Ternary Complex ◽  
Thermal Denaturation ◽  
Binding Constants ◽  
Binding Mode ◽  
Induced Circular Dichroism ◽  
Supportive Evidence ◽  
Equilibrium Binding ◽  
Calf Thymus ◽  
Dna Thermal Denaturation

A study of the interaction with calf thymus DNA is described of a novel set of chiral ternary complex cations of general form [Ru(N4-tet)(phdi)]2+ (where N4-tet is the chiral linear tetradentate R*R*-picchxn or R*R*-picchxnMe2). Individual equilibrium binding constants (KB) have been determined from spectroscopic titrations employing the hypochromism induced in the visible absorbance of the cations on interaction with the nucleic acid. These demonstrate both stereo- and enantioselectivity in the binding interactions. These KB data, together with induced circular dichroism and DNA thermal denaturation results, are all indicative of selective intercalation of the bidentate components of the cations into the nucleobase stack of the duplex. Supportive evidence for a secondary binding mode for the picchxn complexes is provided by the different mutagenicity profiles obtained for related cations.

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