Epicocconone–hemicyanine hybrids: near infrared fluorophores for protein staining and cell imaging

Peter Karuso, Wendy Loa Kum Cheung, Philippe A. Peixoto, Agathe Boulangé, Xavier Franck

Research output: Contribution to journalArticleResearchpeer-review

Abstract

The development of new near infrared (NIR) dyes is crucial for diverse applications and especially bioimaging, as they absorb and emit light in the “therapeutic window“ (650–950 nm). We report here a new family of NIR fluorophores that has been obtained by hybridising hemicyanines with epicocconone. Emission wavelengths of these hybrid dyes is in the range 715–795 nm and is combined with large Stokes’ shifts (75–95 nm). The absorption and emission wavelength can be modulated according to the hemicyanine moiety and adding sulfonic acid moieties enhances water solubility. We demonstrate their application in the sensitive detection of proteins in gel electrophoresis and the staining of specific cellular organelles in confocal microscopy. These results are particularly encouraging and bring forward a new fluorescent skeleton for chemical biology.

LanguageEnglish
Pages1820-1829
Number of pages10
JournalChemistry - A European Journal
Volume23
Issue number8
DOIs
Publication statusPublished - 3 Feb 2017

Fingerprint

Fluorophores
Coloring Agents
Dyes
Staining and Labeling
Infrared radiation
Proteins
Imaging techniques
Wavelength
Sulfonic Acids
Confocal microscopy
Electrophoresis
Skeleton
Confocal Microscopy
Organelles
Solubility
Gels
Light
Acids
Water
tetramethylene hemicyanine

Keywords

  • cyanine
  • epicocconone
  • fluorescent probes
  • imaging agents
  • protein staining

Cite this

Karuso, Peter ; Loa Kum Cheung, Wendy ; Peixoto, Philippe A. ; Boulangé, Agathe ; Franck, Xavier. / Epicocconone–hemicyanine hybrids : near infrared fluorophores for protein staining and cell imaging. In: Chemistry - A European Journal. 2017 ; Vol. 23, No. 8. pp. 1820-1829.
@article{cb3836a7b4dd42c690feee8f077f40b5,
title = "Epicocconone–hemicyanine hybrids: near infrared fluorophores for protein staining and cell imaging",
abstract = "The development of new near infrared (NIR) dyes is crucial for diverse applications and especially bioimaging, as they absorb and emit light in the “therapeutic window“ (650–950 nm). We report here a new family of NIR fluorophores that has been obtained by hybridising hemicyanines with epicocconone. Emission wavelengths of these hybrid dyes is in the range 715–795 nm and is combined with large Stokes’ shifts (75–95 nm). The absorption and emission wavelength can be modulated according to the hemicyanine moiety and adding sulfonic acid moieties enhances water solubility. We demonstrate their application in the sensitive detection of proteins in gel electrophoresis and the staining of specific cellular organelles in confocal microscopy. These results are particularly encouraging and bring forward a new fluorescent skeleton for chemical biology.",
keywords = "cyanine, epicocconone, fluorescent probes, imaging agents, protein staining",
author = "Peter Karuso and {Loa Kum Cheung}, Wendy and Peixoto, {Philippe A.} and Agathe Boulang{\'e} and Xavier Franck",
year = "2017",
month = "2",
day = "3",
doi = "10.1002/chem.201604698",
language = "English",
volume = "23",
pages = "1820--1829",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH, Wiley",
number = "8",

}

Epicocconone–hemicyanine hybrids : near infrared fluorophores for protein staining and cell imaging. / Karuso, Peter; Loa Kum Cheung, Wendy; Peixoto, Philippe A.; Boulangé, Agathe; Franck, Xavier.

In: Chemistry - A European Journal, Vol. 23, No. 8, 03.02.2017, p. 1820-1829.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Epicocconone–hemicyanine hybrids

T2 - Chemistry - A European Journal

AU - Karuso, Peter

AU - Loa Kum Cheung, Wendy

AU - Peixoto, Philippe A.

AU - Boulangé, Agathe

AU - Franck, Xavier

PY - 2017/2/3

Y1 - 2017/2/3

N2 - The development of new near infrared (NIR) dyes is crucial for diverse applications and especially bioimaging, as they absorb and emit light in the “therapeutic window“ (650–950 nm). We report here a new family of NIR fluorophores that has been obtained by hybridising hemicyanines with epicocconone. Emission wavelengths of these hybrid dyes is in the range 715–795 nm and is combined with large Stokes’ shifts (75–95 nm). The absorption and emission wavelength can be modulated according to the hemicyanine moiety and adding sulfonic acid moieties enhances water solubility. We demonstrate their application in the sensitive detection of proteins in gel electrophoresis and the staining of specific cellular organelles in confocal microscopy. These results are particularly encouraging and bring forward a new fluorescent skeleton for chemical biology.

AB - The development of new near infrared (NIR) dyes is crucial for diverse applications and especially bioimaging, as they absorb and emit light in the “therapeutic window“ (650–950 nm). We report here a new family of NIR fluorophores that has been obtained by hybridising hemicyanines with epicocconone. Emission wavelengths of these hybrid dyes is in the range 715–795 nm and is combined with large Stokes’ shifts (75–95 nm). The absorption and emission wavelength can be modulated according to the hemicyanine moiety and adding sulfonic acid moieties enhances water solubility. We demonstrate their application in the sensitive detection of proteins in gel electrophoresis and the staining of specific cellular organelles in confocal microscopy. These results are particularly encouraging and bring forward a new fluorescent skeleton for chemical biology.

KW - cyanine

KW - epicocconone

KW - fluorescent probes

KW - imaging agents

KW - protein staining

UR - http://www.scopus.com/inward/record.url?scp=85007162630&partnerID=8YFLogxK

U2 - 10.1002/chem.201604698

DO - 10.1002/chem.201604698

M3 - Article

VL - 23

SP - 1820

EP - 1829

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 8

ER -