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Near-infrared Fluorescent PH-sensitive Probes Via Unexpected Barbituric Acid Mediated Synthesis

Overview
Journal Org Lett
Specialties Biochemistry
Chemistry
Date 2008 Dec 9
PMID 19061361
Citations 8
Authors
Affiliations
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Abstract

Novel near-infrared pyrimidine-fused pH fluorescent probes were prepared by an unusual barbiturate-mediated debenzoindolation and subsequent heteroannulation. A plausible mechanistic pathway is proposed, and the final structures were further elucidated by 2D-NMR. All new compounds are highly fluorescent in the near-infrared region and possess excellent spectral sensitivities to environmental pH changes.

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References
1.
Peng X, Song F, Lu E, Wang Y, Zhou W, Fan J . Heptamethine cyanine dyes with a large stokes shift and strong fluorescence: a paradigm for excited-state intramolecular charge transfer. J Am Chem Soc. 2005; 127(12):4170-1. DOI: 10.1021/ja043413z. View

2.
Kiyose K, Kojima H, Urano Y, Nagano T . Development of a ratiometric fluorescent zinc ion probe in near-infrared region, based on tricarbocyanine chromophore. J Am Chem Soc. 2006; 128(20):6548-9. DOI: 10.1021/ja060399c. View

3.
Sasaki E, Kojima H, Nishimatsu H, Urano Y, Kikuchi K, Hirata Y . Highly sensitive near-infrared fluorescent probes for nitric oxide and their application to isolated organs. J Am Chem Soc. 2005; 127(11):3684-5. DOI: 10.1021/ja042967z. View

4.
Bouteiller C, Clave G, Bernardin A, Chipon B, Massonneau M, Renard P . Novel water-soluble near-infrared cyanine dyes: synthesis, spectral properties, and use in the preparation of internally quenched fluorescent probes. Bioconjug Chem. 2007; 18(4):1303-17. DOI: 10.1021/bc0700281. View

5.
Ellis A, Mason J, Lee H, Strekowski L, Patonay G, Choi H . Design, synthesis, and characterization of a calcium-sensitive near infrared dye. Talanta. 2008; 56(6):1099-107. DOI: 10.1016/s0039-9140(01)00641-5. View