Literature DB >> 15700995

Latent fluorophore based on the trimethyl lock.

Sunil S Chandran1, Kimberly A Dickson, Ronald T Raines.   

Abstract

Fluorescent molecules are essential for basic research in the biological sciences and have numerous practical applications. Herein is described the synthesis and use of a new class of latent fluorophores based on a novel design element, the trimethyl lock, that confers distinct advantages over extant fluorophores and pro-fluorophores. A diacetyl version of the latent fluorophore is stable in a biological environment, but rapidly yields rhodamine 110 upon acetyl-group hydrolysis by pig liver esterase or endogenous esterases in the cytosol and lysosomes of human cells. This design element is general and, hence, provides access to an ensemble of useful latent fluorophores.

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Year:  2005        PMID: 15700995     DOI: 10.1021/ja043736v

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  22 in total

1.  Fluorogenic label for biomolecular imaging.

Authors:  Luke D Lavis; Tzu-Yuan Chao; Ronald T Raines
Journal:  ACS Chem Biol       Date:  2006-05-23       Impact factor: 5.100

2.  Latent blue and red fluorophores based on the trimethyl lock.

Authors:  Luke D Lavis; Tzu-Yuan Chao; Ronald T Raines
Journal:  Chembiochem       Date:  2006-08       Impact factor: 3.164

Review 3.  Cyclization-activated prodrugs.

Authors:  Paula Gomes; Nuno Vale; Rui Moreira
Journal:  Molecules       Date:  2007-11-12       Impact factor: 4.411

4.  Membrane permeable esterase-activated fluorescent imaging probe.

Authors:  Youngmi Kim; Yongdoo Choi; Ralph Weissleder; Ching-Hsuan Tung
Journal:  Bioorg Med Chem Lett       Date:  2007-07-20       Impact factor: 2.823

5.  Cytotoxic ribonucleases: the dichotomy of Coulombic forces.

Authors:  R Jeremy Johnson; Tzu-Yuan Chao; Luke D Lavis; Ronald T Raines
Journal:  Biochemistry       Date:  2007-08-18       Impact factor: 3.162

6.  Synthesis of fluorogenic polymers for visualizing cellular internalization.

Authors:  Shane L Mangold; Rachael T Carpenter; Laura L Kiessling
Journal:  Org Lett       Date:  2008-06-19       Impact factor: 6.005

7.  A highly sensitive fluorogenic probe for cytochrome P450 activity in live cells.

Authors:  Melissa M Yatzeck; Luke D Lavis; Tzu-Yuan Chao; Sunil S Chandran; Ronald T Raines
Journal:  Bioorg Med Chem Lett       Date:  2008-06-10       Impact factor: 2.823

8.  NEAR-INFRARED DYES: Probe Development and Applications in Optical Molecular Imaging.

Authors:  Donald D Nolting; John C Gore; Wellington Pham
Journal:  Curr Org Synth       Date:  2011-08       Impact factor: 1.975

9.  Sensitive fluorogenic substrate for alkaline phosphatase.

Authors:  Michael N Levine; Ronald T Raines
Journal:  Anal Biochem       Date:  2011-07-24       Impact factor: 3.365

10.  Trimethyl lock: a stable chromogenic substrate for esterases.

Authors:  Michael N Levine; Luke D Lavis; Ronald T Raines
Journal:  Molecules       Date:  2008-01-31       Impact factor: 4.411

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