Synthesis and Characterization of Fluorescence Active G-Quartet and Direct Evaluation of Self-Assembly Impact on Emission

Overview

Journal Chin Chem Lett

Specialty Chemistry

Date 2023 Dec 18

PMID 38107831

Authors

Ying He

Mengjia Liu

Shun Teng

Lukasz Wojtas

Guangxin Gu

Xiaodong Shi

Affiliations

Soon will be listed here.

Abstract

Fluorescence (FL) active 8-aryl guanosine derivatives were prepared and applied for cation mediated self-assembly to form the H-bonded G-quadruplexes. The -cyano (-CN) and 8-anthracene (8-An) substituted guanosines were identified to give the strongest fluorescence with the formation of G-octamers (G) both in solution (NMR) and solid state (X-ray). This well-defined G-octamer system has provided the first direct evidence on the self-assembled G-quadruplex fluorescence emission with aggregation-induced emission (AIE), which could be applied as the foundation for FL molecular probe design toward G-quadruplex recognition.

Citing Articles

Review of the detection of pathogenic Escherichia coli based-microchip technology.

Xue X, Zhang Y Anal Sci. 2024; 41(3):225-236.

PMID: 39654011 DOI: 10.1007/s44211-024-00693-6.

Design and Synthesis of Covalently Tethered "IsoG-Star" as Recyclable Host for Selective Cesium Separation.

Liu M, He Y, Wojtas L, Shi X Green Chem. 2024; 25(21):8494-8499.

PMID: 38765495 PMC: 11101156. DOI: 10.1039/d3gc02932h.

References

Luo D, Mu Y . All-atomic simulations on human telomeric G-quadruplex DNA binding with thioflavin T. J Phys Chem B. 2015; 119(15):4955-67. DOI: 10.1021/acs.jpcb.5b01107. View

Davis J, Spada G . Supramolecular architectures generated by self-assembly of guanosine derivatives. Chem Soc Rev. 2007; 36(2):296-313. DOI: 10.1039/b600282j. View

Xiao S, Lee W, Chen F, Zavalij P, Gutierrez O, Davis J . Oxidation of 8-thioguanosine gives redox-responsive hydrogels and reveals intermediates in a desulfurization pathway. Chem Commun (Camb). 2020; 56(51):6981-6984. DOI: 10.1039/d0cc02926b. View

Biffi G, Tannahill D, McCafferty J, Balasubramanian S . Quantitative visualization of DNA G-quadruplex structures in human cells. Nat Chem. 2013; 5(3):182-6. PMC: 3622242. DOI: 10.1038/nchem.1548. View

He Y, Zhang Y, Liu M, Zhao K, Shan C, Wojtas L . Synthesis of microporous hydrogen-bonded supramolecular organic frameworks through guanosine self-assembly. Cell Rep Phys Sci. 2022; 2(8). PMC: 9162061. DOI: 10.1016/j.xcrp.2021.100519. View

Hong Y, Lam J, Tang B . Aggregation-induced emission. Chem Soc Rev. 2011; 40(11):5361-88. DOI: 10.1039/c1cs15113d. View

Dumas A, Luedtke N . Highly fluorescent guanosine mimics for folding and energy transfer studies. Nucleic Acids Res. 2011; 39(15):6825-34. PMC: 3159459. DOI: 10.1093/nar/gkr281. View

Zhang Y, He Y, Wojtas L, Shi X, Guo H . Construction of Supramolecular Organogel with Circularly Polarized Luminescence by Self-Assembled Guanosine Octamer. Cell Rep Phys Sci. 2020; 1(10). PMC: 7654816. DOI: 10.1016/j.xcrp.2020.100211. View

Kwok R, Leung C, Lam J, Tang B . Biosensing by luminogens with aggregation-induced emission characteristics. Chem Soc Rev. 2014; 44(13):4228-38. DOI: 10.1039/c4cs00325j. View

10.

Lee M, Sharma A, Chang M, Lee J, Son S, Sessler J . Fluorogenic reaction-based prodrug conjugates as targeted cancer theranostics. Chem Soc Rev. 2017; 47(1):28-52. PMC: 5750141. DOI: 10.1039/c7cs00557a. View

11.

Peters G, Skala L, Davis J . A Molecular Chaperone for G4-Quartet Hydrogels. J Am Chem Soc. 2015; 138(1):134-9. DOI: 10.1021/jacs.5b08769. View

12.

He Y, Zhang Y, Wojtas L, Akhmedov N, Pan Q, Guo H . Reversed Cation Selectivity of G -Octamer and G -Hexadecamer towards Monovalent and Divalent Cations. Chem Asian J. 2020; 15(7):1030-1034. PMC: 7138703. DOI: 10.1002/asia.202000016. View

13.

Lane A, Brad Chaires J, Gray R, Trent J . Stability and kinetics of G-quadruplex structures. Nucleic Acids Res. 2008; 36(17):5482-515. PMC: 2553573. DOI: 10.1093/nar/gkn517. View

14.

Umar M, Ji D, Chan C, Kwok C . G-Quadruplex-Based Fluorescent Turn-On Ligands and Aptamers: From Development to Applications. Molecules. 2019; 24(13). PMC: 6650947. DOI: 10.3390/molecules24132416. View

15.

Martin-Arroyo M, Del Prado A, Chamorro R, Bilbao N, Gonzalez-Rodriguez D . Elucidating Noncovalent Reaction Mechanisms: G-Quartet as an Intermediate in G-Quadruplex Assembly. Angew Chem Int Ed Engl. 2020; 59(23):9041-9046. DOI: 10.1002/anie.201916261. View

16.

Blanchard D, Cservenyi T, Manderville R . Dual fluorescent deoxyguanosine mimics for FRET detection of G-quadruplex folding. Chem Commun (Camb). 2015; 51(94):16829-31. DOI: 10.1039/c5cc07154b. View

17.

He Y, Zhang Y, Wojtas L, Akhmedov N, Thai D, Wang H . Construction of a cross-layer linked G-octamer conformational control: a stable G-quadruplex in H-bond competitive solvents. Chem Sci. 2019; 10(15):4192-4199. PMC: 6471798. DOI: 10.1039/c9sc00190e. View

18.

Bochman M, Paeschke K, Zakian V . DNA secondary structures: stability and function of G-quadruplex structures. Nat Rev Genet. 2012; 13(11):770-80. PMC: 3725559. DOI: 10.1038/nrg3296. View

19.

Fadock K, Manderville R, Sharma P, Wetmore S . Optimization of fluorescent 8-heteroaryl-guanine probes for monitoring protein-mediated duplex → G-quadruplex exchange. Org Biomol Chem. 2016; 14(19):4409-19. DOI: 10.1039/c6ob00474a. View

20.

Sutyak K, Lee W, Zavalij P, Gutierrez O, Davis J . Templating and Catalyzing [2+2] Photocycloaddition in Solution Using a Dynamic G-Quadruplex. Angew Chem Int Ed Engl. 2018; 57(52):17146-17150. DOI: 10.1002/anie.201811202. View