Research Progress in Cyanine-Based Recognition Probes for G-Quadruplex DNA

doi:10.6023/cjoc202203025

Abstract

Guanine-rich (G) DNA sequences can form a special nucleic acid secondary structure called G-quadruplex DNA, which is widely distributed in eukaryotic genomes and is closely associated with the formation and development of cancer. The development of small molecule fluorescent probes targeting G-quadruplexes is of great significance for the study of the biological functions of G-quadruplexes in organisms and for targeting anti-cancer drugs. The cyanine dyes are widely used as fluorescent dyes for biolabelling, with the advantages of multiple modification sites and adjustable spectral range. The rigid structural part of the backbone can be bound to the end of the G-quadruplex or groove through π-π stacking, hydrophobic interaction and other non-covalent bonding, inducing different spectral signal changes of cyanine dyes to achieve selective recognition of the G-quadruplex. This has become a hot topic of research in the field of G-quadruplex recognition in recent years. Herein, the research progresses in the field of G‑quadruplex recognition probes based on cyanine dye are reviewed. Molecular design and propertis of this kind of probes are briefly introduced, and the affinity and selectivity of probes for G-quadruplex DNA are also commented. Moreover, the future trends of cyanine-based recognition probes for G‑quadruplex are briefly introduced.

Key words: cyanine dye, G-quadruplex DNA, recognition probe, molecular design

Cite this article

Li Guan, Yongbao Mao, Yanyan Zhou, Xiaowen Feng, Yile Fu. Research Progress in Cyanine-Based Recognition Probes for G-Quadruplex DNA[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2406-2417.

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G4探针	λ_max/λ_em^a/nm	结合/解离常数^b	选择性	识别方法	靶向细胞器
2	≈520/≈550	—	G4s	荧光^c	—
3	527/584	0.25×10⁶ L•mol^–1	G4s	荧光	细胞核
4c	552/585	1.12×10⁶ L•mol^–1	G4s	荧光	细胞核
5	516/613	—	G4s	比色^d, 荧光	细胞质、核(主要)
6a	473/630	0.965×10⁶ L•mol^–1	G4s	荧光	细胞核仁
6b	425/≈550	6 μmol•L^–1	混合型端粒G4s	比色, 荧光	细胞核为主
6f	/650	—	G4s	荧光	线粒体
6g	/530	—	G4s	荧光	线粒体
6h	448/≈650	1.5~10.5 μmol•L^–1	G4s	荧光	线粒体
6i	525/630	0.69~11.8 μmol•L^–1	选择性较差	荧光	细胞核
6j	561/694	(0.319~0.929)×10⁶ L•mol^–1	反平行端粒G4s	荧光	线粒体
7	535/	0.429~0.735 μmol•L^–1	G4s	比色	—
8	515/588	2.00~2.35 μmol•L^–1	平行G4s	荧光	—
14	646/680	0.48×10⁶ L•mol^–1	平行MYC G4s	荧光	—
15	599/651	(11.2~39.7)×10⁶ L•mol^–1	G4s	荧光	—
17	499/650	2.08×10⁶ L•mol^–1	端粒G4s	荧光	细胞核仁
18	440/480	—	G4s	荧光	溶酶体
22	607/602	—	分子内平行和混合G4s	比色, 荧光	—
23	480/530	—	平行MYC G4s	荧光	—
25	450/604	(0.12~0.65)×10⁶ L•mol^–1	平行MYC G4s	比色, 荧光	—
26	553/	—	椅式反平行G4s	CD	—
27a	577/715	0.82×10⁶ L•mol^–1	G4s	荧光	—
27b	630/700	(0.18~2)×10⁶ L•mol^–1	G4s	比色	—
27c	626/	9.3×10⁶ L•mol^–1	G4s	荧光	—
28	516/550	(0.13~3.16) μmol•L^–1	G4s	荧光	—
30	613/710	(8.93~19.7) μmol•L^–1	平行G4s	比色, 荧光	—
31	620, 800/700	k₁: (0.12~0.9)×10⁶ L•mol^–1 k₂: (0.036~0.27)×10⁶ L•mol^–1	平行G4s	比色, 荧光	—

G4探针	λ_max/λ_em^a/nm	结合/解离常数^b	选择性	识别方法	靶向细胞器
2	≈520/≈550	—	G4s	荧光^c	—
3	527/584	0.25×10⁶ L•mol^–1	G4s	荧光	细胞核
4c	552/585	1.12×10⁶ L•mol^–1	G4s	荧光	细胞核
5	516/613	—	G4s	比色^d, 荧光	细胞质、核(主要)
6a	473/630	0.965×10⁶ L•mol^–1	G4s	荧光	细胞核仁
6b	425/≈550	6 μmol•L^–1	混合型端粒G4s	比色, 荧光	细胞核为主
6f	/650	—	G4s	荧光	线粒体
6g	/530	—	G4s	荧光	线粒体
6h	448/≈650	1.5~10.5 μmol•L^–1	G4s	荧光	线粒体
6i	525/630	0.69~11.8 μmol•L^–1	选择性较差	荧光	细胞核
6j	561/694	(0.319~0.929)×10⁶ L•mol^–1	反平行端粒G4s	荧光	线粒体
7	535/	0.429~0.735 μmol•L^–1	G4s	比色	—
8	515/588	2.00~2.35 μmol•L^–1	平行G4s	荧光	—
14	646/680	0.48×10⁶ L•mol^–1	平行MYC G4s	荧光	—
15	599/651	(11.2~39.7)×10⁶ L•mol^–1	G4s	荧光	—
17	499/650	2.08×10⁶ L•mol^–1	端粒G4s	荧光	细胞核仁
18	440/480	—	G4s	荧光	溶酶体
22	607/602	—	分子内平行和混合G4s	比色, 荧光	—
23	480/530	—	平行MYC G4s	荧光	—
25	450/604	(0.12~0.65)×10⁶ L•mol^–1	平行MYC G4s	比色, 荧光	—
26	553/	—	椅式反平行G4s	CD	—
27a	577/715	0.82×10⁶ L•mol^–1	G4s	荧光	—
27b	630/700	(0.18~2)×10⁶ L•mol^–1	G4s	比色	—
27c	626/	9.3×10⁶ L•mol^–1	G4s	荧光	—
28	516/550	(0.13~3.16) μmol•L^–1	G4s	荧光	—
30	613/710	(8.93~19.7) μmol•L^–1	平行G4s	比色, 荧光	—
31	620, 800/700	k₁: (0.12~0.9)×10⁶ L•mol^–1 k₂: (0.036~0.27)×10⁶ L•mol^–1	平行G4s	比色, 荧光	—

基于菁染料骨架的G-四链体DNA识别探针的研究进展