Polarity-Sensitive Coumarins Tailored to Live Cell Imaging.
Polarity-dependent fluorescent probes are recently attracting interest for high-resolution cell imaging. Following a stepwise rational approach, we prepared and tested a toolbox of new coumarin derivatives tailored to in vivo imaging applications. Our compounds are characterized by a donor-(coumarin...
| Publicado en: | Journal of the American Chemical Society Vol. 132; no. 4; pp. 1276 - 1289 |
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| Autores principales: | , , , , |
| Formato: | Artículo |
| Publicado: |
American Chemical Society
2/3/2010
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| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=48141282&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 48141282 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 2/3/2010 vid: 132 iid: 4 pid: 997 pub: American Chemical Society artinfo: ui: 48141282 10.1021/ja9050444 ppf: 1276 ppct: 13 formats: tig: atl: Polarity-Sensitive Coumarins Tailored to Live Cell Imaging. aug: au: Signore, Giovanni Nifosì, Riccardo AIbertazzi, Lorenzo Storti, Barbara Bizzarri, Ranieri affil: NEST, Scuola Normale Superiore, IIT@NEST, Center for Nanotechnology Innovation, p.za San Silvestro 12, 1-56127 Pisa, Italy NEST, CNR-INFM, p.za San Silvestro 12, 56127 Pisa, Italy su: Cells Imaging systems Fluorescent probes Fluorescence spectroscopy Coumarins Cell polarity Electrophiles Molecular biology sug: subj: Cells Imaging systems Fluorescent probes Fluorescence spectroscopy Coumarins Cell polarity Electrophiles Molecular biology ab: Polarity-dependent fluorescent probes are recently attracting interest for high-resolution cell imaging. Following a stepwise rational approach, we prepared and tested a toolbox of new coumarin derivatives tailored to in vivo imaging applications. Our compounds are characterized by a donor-(coumarin core)-acceptor molecular structure, where the electron donor is represented by alkylether or naphthyl groups, and the electron acceptor is represented by benzothiazene and cyano groups. Prior to synthesis, the substitution patterns were screened by computational methods to provide functional fluorescent derivatives easy to synthesize, and with excitation in the visible region of spectrum. We set up a robust synthetic procedure tunable on the substitution patterns to achieve. These coumarins possess excellent fluorescence quantum yields (up to 0.95), high molar extinction coefficients (up to 46,000 M cm), and large Stokes shifts. Furthermore, they display strong solvatochromism, being almost non-emissive in water and very fluorescent in less polar media (up to 780-fold enhancement in brightness). The solvatochromism of these compounds can be accounted for by a photophysical method encompassing two communicating excited states. When tested on cultured cells, the results showed that the developed coumarins were not harmful and their photophysical properties were unchanged compared to free solution. According to the determined solvatochromic properties, the coumarin fluorescence was detected only in the most lipophilic environments of the cell. The prepared compounds represent remarkable tools to investigate subtle biochemical processes in the cell environment after appropriate conjugation to biomolecules, and at the same time constitute the basis for further engineering of a new generation of biosensors. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2010 holdings: @attributes: islocal: N |
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