Asymmetric Monomethine Cyanine Dyes with Hydrophobic Functionalities for Fluorescent Intercalator Displacement Assay

被引：1

作者：

Ilieva, Sonia ^{[1
]}

Bozova, Nadezhda ^{[1
]}

Rangelov, Miroslav ^{[2
]}

Todorova, Nadezhda ^{[3
]}

Vasilev, Aleksey ^{[1
,4
]}

Cheshmedzhieva, Diana ^{[1
]}

机构：

[1] Sofia Univ St Kliment Ohridski, Fac Chem & Pharm, 1 J Bourchier Ave, Sofia 1164, Bulgaria

[2] Bulgarian Acad Sci, Inst Organ Chem Ctr Phytochemistry, Sofia 1113, Bulgaria

[3] Bulgarian Acad Sci, Inst Biodivers & Ecosyst Res, Sofia 1113, Bulgaria

[4] Bulgarian Acad Sci, Inst Polymers, Bonchev St,Bl 103A, Sofia 1113, Bulgaria

来源：

MOLECULES | 2024年 / 29卷 / 01期

关键词：

asymmetric monomethine cyanine dyes; RNA; DNA; fluorescence titration; biomolecular probes; DFT; TDDFT; DNA-BINDING AFFINITY; THIAZOLE ORANGE; DISTAMYCIN; CHEMISTRY; DISCOVERY; ANALOGS;

D O I：

10.3390/molecules29010114

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A new green procedure has been applied for the synthesis and purification of asymmetric monomethine cyanine dyes. The photophysical properties of the newly synthesized compounds have been examined by combined application of spectroscopic and theoretical methods. The structural characteristics of the molecules and dimer formation were characterized by quantum chemical computation and juxtaposed to the aggregachromism in UV/Vis spectra. The applicability of the dyes as fluorogenic nucleic acid probes has been proven by fluorescence titration, and their binding constants have been calculated. The mode of ligand-dsDNA/RNA interaction was rationalized by means of CD spectroscopy, molecular docking analysis, and fluorescent intercalator displacement experiments.

引用

页数：16

共 37 条

[31] UTILITY OF INTENSELY FLUORESCENT CYANINE DYES (CY3) FOR ASSAY OF GAP JUNCTIONAL COMMUNICATION BY DYE-TRANSFER
HOSSAIN, MZ
ERNST, LA
NAGY, JI
NEUROSCIENCE LETTERS, 1995, 184 (01) : 71 - 74
[32] Label-free detection of kanamycin based on a G-quadruplex DNA aptamer-based fluorescent intercalator displacement assay
Yun-Peng Xing
Chun Liu
Xiao-Hong Zhou
Han-Chang Shi
Scientific Reports, 5
[33] Development of a fluorescent intercalator displacement assay (G4-FID) for establishing quadruplex-DNA affinity and selectivity of putative ligands
Monchaud, David
Allain, Clemence
Teulade-Fichou, Marie-Paule
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (18) : 4842 - 4845
[34] Label-free detection of kanamycin based on a G-quadruplex DNA aptamer-based fluorescent intercalator displacement assay
Xing, Yun-Peng
Liu, Chun
Zhou, Xiao-Hong
Shi, Han-Chang
SCIENTIFIC REPORTS, 2015, 5
[35] Detection of Cordycepin Using Indicator Displacement Assay of Cucurbit [7] Uril and Environmentally Sensitive Fluorescent Dyes
Dewantari, Arinta Agnie
Nakprach, Tanapat
Wongkongkatep, Jirarut
9TH ANNUAL BASIC SCIENCE INTERNATIONAL CONFERENCE 2019 (BASIC 2019), 2019, 546
[36] Fluorescent intercalator displacement replacement (FIDR) assay: determination of relative thermodynamic and kinetic parameters in triplex formation-a case study using triplex-forming LNAs
Sau, Sujay P.
Kumar, Pawan
Sharma, Pawan K.
Hrdlicka, Patrick J.
NUCLEIC ACIDS RESEARCH, 2012, 40 (21)
[37] Novel synthetic approach to asymmetric monocationic trimethine cyanine dyes derived from N-ethyl quinolinum moiety. Combined fluorescent and ICD probes for AT-DNA labelling
Kurutos, Atanas
Crnolatac, Ivo
Orehovec, Iva
Gadjev, Nikolai
Piantanida, Ivo
Deligeorgiev, Todor
JOURNAL OF LUMINESCENCE, 2016, 174 : 70 - 76

← 1 2 3 4 →