Synthesis and Photophysical Study of 2'-deoxyuridines Labeled with Fluorene Derivatives

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2012 Oct 23

PMID 23085656

Citations 3

Authors

Hyun Yi Cho

Sang Keun Woo

Gil Tae Hwang

Affiliations

Soon will be listed here.

Abstract

We examined microenvironment-sensitive fluorescent 2'-deoxyuridines labeled with fluorene derivatives that exhibited solvent-dependent photophysical properties. The high sensitivity of the fluorescence shift and the nucleoside intensity dependence on solvent polarity provided information useful for estimating the polarity of the environment surrounding the fluorescent nucleoside.

Citing Articles

The linkers in fluorene-labeled 2'-deoxyuridines affect fluorescence discriminating phenomena upon duplex formation.

Lee S, Hong S, Yeo H, Hwang G RSC Adv. 2022; 10(32):18853-18859.

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Single-Labeled Oligonucleotides Showing Fluorescence Changes Upon Hybridization with Target Nucleic Acids.

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Synthesis and optical behaviors of 6-seleno-deoxyguanosine.

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References

Sinkeldam R, Marcus P, Uchenik D, Tor Y . Multisensing emissive pyrimidine. Chemphyschem. 2011; 12(12):2260-5. PMC: 3365504. DOI: 10.1002/cphc.201100315. View

Varghese R, Wagenknecht H . Non-covalent versus covalent control of self-assembly and chirality of Nile red-modified nucleoside and DNA. Chemistry. 2010; 16(30):9040-6. DOI: 10.1002/chem.201001136. View

Hwang G, Son H, Ku J, Kim B . Synthesis and photophysical studies of bis-enediynes as tunable fluorophores. J Am Chem Soc. 2005; 125(37):11241-8. DOI: 10.1021/ja0349148. View

Tanaka M, Oguma K, Saito Y, Saito I . Enhancement of fluorescence quenching and exciplex formation in DNA major groove by double incorporation of modified fluorescent deoxyuridines. Bioorg Med Chem Lett. 2012; 22(12):4103-5. DOI: 10.1016/j.bmcl.2012.04.067. View

Pawar M, Srivatsan S . Synthesis, photophysical characterization, and enzymatic incorporation of a microenvironment-sensitive fluorescent uridine analog. Org Lett. 2011; 13(5):1114-7. DOI: 10.1021/ol103147t. View

Sinkeldam R, Tor Y . To D or not to D? On estimating the microenvironment polarity of biomolecular cavities. Org Biomol Chem. 2007; 5(16):2523-8. DOI: 10.1039/b707719j. View

Sinkeldam R, Greco N, Tor Y . Polarity of major grooves explored by using an isosteric emissive nucleoside. Chembiochem. 2008; 9(5):706-9. DOI: 10.1002/cbic.200700714. View

Saito Y, Miyamoto S, Suzuki A, Matsumoto K, Ishihara T, Saito I . Fluorescent nucleosides with 'on-off' switching function, pH-responsive fluorescent uridine derivatives. Bioorg Med Chem Lett. 2012; 22(8):2753-6. DOI: 10.1016/j.bmcl.2012.02.092. View

Venkatesan N, Seo Y, Kim B . Quencher-free molecular beacons: a new strategy in fluorescence based nucleic acid analysis. Chem Soc Rev. 2008; 37(4):648-63. DOI: 10.1039/b705468h. View

10.

Ostergaard M, Hrdlicka P . Pyrene-functionalized oligonucleotides and locked nucleic acids (LNAs): tools for fundamental research, diagnostics, and nanotechnology. Chem Soc Rev. 2011; 40(12):5771-88. PMC: 3644995. DOI: 10.1039/c1cs15014f. View

11.

Wilson J, Kool E . Fluorescent DNA base replacements: Reporters and sensors for biological systems. Org Biomol Chem. 2006; 4(23):4265-74. DOI: 10.1039/b612284c. View

12.

Hwang G, Seo Y, Kim B . A highly discriminating quencher-free molecular beacon for probing DNA. J Am Chem Soc. 2004; 126(21):6528-9. DOI: 10.1021/ja049795q. View

13.

Tanaka M, Oguma K, Saito Y, Saito I . Drastic enhancement of excess electron-transfer efficiency through DNA by inserting consecutive 5-phenylethynyl-2'-deoxyuridines as a modulator. Chem Commun (Camb). 2012; 48(75):9394-6. DOI: 10.1039/c2cc34661c. View

14.

Ranasinghe R, Brown T . Fluorescence based strategies for genetic analysis. Chem Commun (Camb). 2005; (44):5487-502. DOI: 10.1039/b509522k. View

15.

Jozefowicz M . Determination of reorganization energy of fluorenone and 4-hydroxyfluorenone in neat and binary solvent mixtures. Spectrochim Acta A Mol Biomol Spectrosc. 2006; 67(2):444-9. DOI: 10.1016/j.saa.2006.07.038. View

16.

Bag S, Kundu R, Matsumoto K, Saito Y, Saito I . Singly and doubly labeled base-discriminating fluorescent oligonucleotide probes containing oxo-pyrene chromophore. Bioorg Med Chem Lett. 2010; 20(11):3227-30. DOI: 10.1016/j.bmcl.2010.04.063. View

17.

Ostergaard M, Guenther D, Kumar P, Baral B, Deobald L, Paszczynski A . Pyrene-functionalized triazole-linked 2'-deoxyuridines-probes for discrimination of single nucleotide polymorphisms (SNPs). Chem Commun (Camb). 2010; 46(27):4929-31. DOI: 10.1039/c0cc01133a. View

18.

Sinkeldam R, Greco N, Tor Y . Fluorescent analogs of biomolecular building blocks: design, properties, and applications. Chem Rev. 2010; 110(5):2579-619. PMC: 2868948. DOI: 10.1021/cr900301e. View

19.

Dai N, Kool E . Fluorescent DNA-based enzyme sensors. Chem Soc Rev. 2011; 40(12):5756-70. PMC: 5575859. DOI: 10.1039/c0cs00162g. View