Abstract
A novel water-soluble 2-[2-(2-chloro-3-{2-[3,3-dimethyl-5-sulfo-1-(4-sulfo-butyl)-3H-indol-2-yl]-vinyl}-cyclohex-2-enylidene)-ethylidene]-3,3-dimethyl-1-(4-sulfo-butyl)-2,3-dihydro-1H-indole-5-carboxylic acid (dye 2) was developed via an asymmetric approach. With an additional sulfonate group, the near-infrared feature of this dye exhibited a 2-fold increase in quantum yield compared to the previous generation. The current synthetic strategy provided a single carboxylic group as a handle for conjugation, thus allowing selectivity for bioconjugation. The stability of this dye was demonstrated by labeling peptides via solid-phase peptide chemistry. The in vivo optical imaging showed potential and broad applications of this dye in developing molecular-based beacons for cancer detection.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, P.H.S.
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Technical Report
MeSH terms
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Animals
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Cell Line, Tumor
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Coloring Agents / chemical synthesis
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Coloring Agents / chemistry*
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Coloring Agents / radiation effects*
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Cyclohexanes / chemical synthesis*
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Cyclohexanes / chemistry
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Diagnostic Imaging / instrumentation*
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Diagnostic Imaging / methods*
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Humans
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Indoles / chemical synthesis*
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Indoles / chemistry
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Infrared Rays*
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Mice
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Mice, Nude
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Microscopy, Fluorescence
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Molecular Structure
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Neoplasms / diagnosis*
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Solubility
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Spectrometry, Fluorescence
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Water / chemistry*
Substances
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2-(2-(2-chloro-3-(2-(3,3-dimethyl-5-sulfo-1-(4-sulfo-butyl)-3H-indol-2-yl)-vinyl)-cyclohex-2-enylidene)-ethylidene)-3,3-dimethyl-1-(4-sulfo-butyl)-2,3-dihydro-1H-indole-5-carboxylic acid
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Coloring Agents
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Cyclohexanes
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Indoles
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Water