A Fluorescent Guanosine Dinucleoside as a Selective Switch-On Sensor for c-myc G-Quadruplex DNA with Potent Anticancer Activities

被引:23
|
作者
Kumar, Y. Pavan [1 ]
Bhowmik, Sudipta [1 ]
Das, Rabindra Nath [2 ]
Bessi, Irene [3 ,4 ]
Paladhi, Sushovan [1 ]
Ghosh, Rita [5 ]
Schwalbe, Harald [3 ,4 ]
Dash, Jyotirmayee [1 ,2 ]
机构
[1] Indian Assoc Cultivat Sci Jadavpur, Dept Organ Chem, Kolkata 700032, India
[2] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741252, W Bengal, India
[3] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60438 Frankfurt, Germany
[4] Ctr Biomol Magnet Resonance, D-60438 Frankfurt, Germany
[5] Univ Kalyani, Dept Biochem & Biophys, Kalyani 741235, W Bengal, India
关键词
cell cycles; click chemistry; fluorescence; nucleosides; G-quadruplex DNA; G-QUARTETS; PROBES; LOGIC; CHEMISTRY; APOPTOSIS; DYES; RNA;
D O I
10.1002/chem.201302107
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Like likes like! A novel fluorescent C2-symmetric guanosine-based dinucleoside has been engineered by chemical ligation of two guanosine units with a biocompatible dansyl tag. The nucleoside exhibits high selectivity for c-myc G-quadruplex DNA through fluorescence enhancement over duplex DNA and other promoter G-quadruplexes (see scheme). It stains the nucleus preferentially, arrests the cell cycle at the G2/M phase, inhibits cell growth, and induces apoptosis in A375 cancer cells. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11502 / 11506
页数:5
相关论文
共 43 条
  • [31] Elucidating the stabilization mechanism of a K +-depleted c-MYC DNA G-quadruplex in hydrophobic imidazolium-based ionic liquids using spectroscopy coupled with molecular dynamics simulations
    Paradis, Nicholas J.
    Clark, Austin
    Dutta, Achismita
    Gogoj, Hunter
    Vaden, Timothy D.
    Wu, Chun
    JOURNAL OF MOLECULAR LIQUIDS, 2024, 399
  • [32] Iridium(III) complexes with 1,10-phenanthroline-based NN ligands as highly selective luminescent G-quadruplex probes and application for switch-on ribonuclease H detection
    Lu, Lihua
    Wang, Wanhe
    Yang, Chao
    Kang, Tian-Shu
    Leung, Chung-Hang
    Ma, Dik-Lung
    JOURNAL OF MATERIALS CHEMISTRY B, 2016, 4 (42) : 6791 - 6796
  • [33] Synthesis and characterization of chiral ruthenium(II) complexes Λ/Δ-[Ru(bpy)2(H2iip)](ClO4)2 as stabilizers of c-myc G-quadruplex DNA
    Zhang, Zhao
    Mei, Wenjie
    Wu, Xiaohui
    Wang, Xicheng
    Wang, Baoguo
    Chen, Sidong
    JOURNAL OF COORDINATION CHEMISTRY, 2015, 68 (08) : 1465 - 1475
  • [34] 5-Bromo-oxoisoaporphine platinum(II) complexes exhibit tumor cell cytotoxcicity via inhibition of telomerase activity and disruption of c-myc G-quadruplex DNA and mitochondrial functions
    Wei, Zu-Zhuang
    Qin, Qi-Pin
    Meng, Tiny
    Deng, Cai-Xing
    Liang, Hong
    Chen, Zhen-Feng
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 145 : 360 - 369
  • [35] Binding symmetric porphyrins to the c-MYC promoter Pu24I G-quadruplex: toward more specific ligand recognition by flanking bases
    Stankovic, Ivana
    Zrilic, Sonja
    Milovanovic, Branislav
    Stanojevic, Ana
    Petkovic, Milena
    Etinski, Mihajlo
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (23) : 11176 - 11187
  • [36] Design, Synthesis, and Evaluation of New Selective NM23-H2 Binders as c-MYC Transcription Inhibitors via Disruption of the NM23-H2/G-Quadruplex Interaction
    Wang, Yu-Qing
    Huang, Zhou-Li
    Chen, Shuo-Bin
    Wang, Chen-Xi
    Shan, Chan
    Yin, Qi-Kun
    Ou, Tian-Miao
    Li, Ding
    Gu, Lian-Quan
    Tan, Jia-Heng
    Huang, Zhi-Shu
    JOURNAL OF MEDICINAL CHEMISTRY, 2017, 60 (16) : 6924 - 6941
  • [37] Synthesis, characterization of ruthenium(II) complex of 1,3,8-trihydroxy-6-methyl-anthraquinone (emodin) and its binding behavior with c-myc G-quadruplex
    Zhang, Zhao
    Wu, Xiao-Hui
    Sun, Fu-Qiang
    Shan, Feng
    Chen, Jin-Chan
    Chen, Lan-Mei
    Zhou, Yi-Sheng
    Mei, Wen-Jie
    INORGANICA CHIMICA ACTA, 2014, 418 : 23 - 29
  • [38] Exploring the Parallel G-Quadruplex Nucleic Acid World: A Spectroscopic and Computational Investigation on the Binding of the c-myc Oncogene NHE III1 Region by the Phytochemical Polydatin
    Greco, Francesca
    Musumeci, Domenica
    Borbone, Nicola
    Falanga, Andrea Patrizia
    Terracciano, Monica
    Piccialli, Ilaria
    Roviello, Giovanni Nicola
    Oliviero, Giorgia
    MOLECULES, 2022, 27 (09):
  • [39] Rational design of Red fluorescent and selective G-quadruplex DNA sensing probes: The study of interaction signaling and the molecular structural relationship achieving high specificity
    Zheng, Bo-Xin
    Long, Wei
    Zhang, Yi-Han
    Huang, Xuan-He
    Chen, Cui-Cui
    Zhong, Dong-Xiao
    She, Meng-Ting
    Chen, Ze-Xin
    Cai, Dong-Peng
    Lu, Yu-Jing
    Wong, Wing-Leung
    SENSORS AND ACTUATORS B-CHEMICAL, 2020, 314
  • [40] Tanshinone IIA derivatives induced S-phase arrest through stabilizing c-myc G-quadruplex DNA to regulate ROS-mediated PI3K/Akt/mTOR pathway
    Wang, Teng
    Zou, Jun
    Wu, Qiong
    Wang, Rui
    Yuan, Chan-Ling
    Shu, Jing
    Zhai, Bing-Bing
    Huang, Xiao-Ting
    Liu, Ning-Zhi
    Hua, Feng-Yang
    Wang, Xi-Cheng
    Mei, Wen-Jie
    EUROPEAN JOURNAL OF PHARMACOLOGY, 2021, 912