Abstract
The detection of chemical or biological analytes upon molecular reactions relies increasingly on fluorescence methods, and there is a demand for more sensitive, more specific, and more versatile fluorescent molecules. We have designed long wavelength fluorogenic probes with a turn-ON mechanism based on a donor-two-acceptor π-electron system that can undergo an internal charge transfer to form new fluorochromes with longer π-electron systems. Several latent donors and multiple acceptor molecules were incorporated into the probe modular structure to generate versatile dye compounds. This new library of dyes had fluorescence emission in the near-infrared (NIR) region. Computational studies reproduced the observed experimental trends well and suggest factors responsible for high fluorescence of the donor-two-acceptor active form and the low fluorescence observed from the latent form. Confocal images of HeLa cells indicate a lysosomal penetration pathway of a selected dye. The ability of these dyes to emit NIR fluorescence through a turn-ON activation mechanism makes them promising candidate probes for in vivo imaging applications.
| Original language | English |
|---|---|
| Pages (from-to) | 20412-20420 |
| Number of pages | 9 |
| Journal | Journal of the American Chemical Society |
| Volume | 134 |
| Issue number | 50 |
| DOIs | |
| Publication status | Published - Dec 19 2012 |
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ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
- Biochemistry
- Colloid and Surface Chemistry
Cite this
"donor-two-acceptor" dye design : A distinct gateway to NIR fluorescence. / Karton-Lifshin, Naama; Albertazzi, Lorenzo; Bendikov, Michael; Baran, Phil S.; Shabat, Doron.
In: Journal of the American Chemical Society, Vol. 134, No. 50, 19.12.2012, p. 20412-20420.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - "donor-two-acceptor" dye design
T2 - A distinct gateway to NIR fluorescence
AU - Karton-Lifshin, Naama
AU - Albertazzi, Lorenzo
AU - Bendikov, Michael
AU - Baran, Phil S.
AU - Shabat, Doron
PY - 2012/12/19
Y1 - 2012/12/19
N2 - The detection of chemical or biological analytes upon molecular reactions relies increasingly on fluorescence methods, and there is a demand for more sensitive, more specific, and more versatile fluorescent molecules. We have designed long wavelength fluorogenic probes with a turn-ON mechanism based on a donor-two-acceptor π-electron system that can undergo an internal charge transfer to form new fluorochromes with longer π-electron systems. Several latent donors and multiple acceptor molecules were incorporated into the probe modular structure to generate versatile dye compounds. This new library of dyes had fluorescence emission in the near-infrared (NIR) region. Computational studies reproduced the observed experimental trends well and suggest factors responsible for high fluorescence of the donor-two-acceptor active form and the low fluorescence observed from the latent form. Confocal images of HeLa cells indicate a lysosomal penetration pathway of a selected dye. The ability of these dyes to emit NIR fluorescence through a turn-ON activation mechanism makes them promising candidate probes for in vivo imaging applications.
AB - The detection of chemical or biological analytes upon molecular reactions relies increasingly on fluorescence methods, and there is a demand for more sensitive, more specific, and more versatile fluorescent molecules. We have designed long wavelength fluorogenic probes with a turn-ON mechanism based on a donor-two-acceptor π-electron system that can undergo an internal charge transfer to form new fluorochromes with longer π-electron systems. Several latent donors and multiple acceptor molecules were incorporated into the probe modular structure to generate versatile dye compounds. This new library of dyes had fluorescence emission in the near-infrared (NIR) region. Computational studies reproduced the observed experimental trends well and suggest factors responsible for high fluorescence of the donor-two-acceptor active form and the low fluorescence observed from the latent form. Confocal images of HeLa cells indicate a lysosomal penetration pathway of a selected dye. The ability of these dyes to emit NIR fluorescence through a turn-ON activation mechanism makes them promising candidate probes for in vivo imaging applications.
UR - http://www.scopus.com/inward/record.url?scp=84871364797&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84871364797&partnerID=8YFLogxK
U2 - 10.1021/ja308124q
DO - 10.1021/ja308124q
M3 - Article
C2 - 23194283
AN - SCOPUS:84871364797
VL - 134
SP - 20412
EP - 20420
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 50
ER -