The synthesis of new fluorescent bichromophoric compounds as ratiometric pH probes for intracellular measurements
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Other documents of the author: Saura Centelles, Ana Vanessa; Marín, María J.; Burguete, M. Isabel; Russell, David A.; Galindo, Francisco; Luis, Santiago V.
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Title
The synthesis of new fluorescent bichromophoric compounds as ratiometric pH probes for intracellular measurementsAuthor (s)
Date
2015Publisher
Royal Society of ChemistryISSN
1477-0520; 1477-0539Bibliographic citation
Saura, Vanessa, Marin Altaba, Maria, Burguete, M. Isabel, Russell, David, Galindo, Francisco and Luis, Santiago V. (2015) Synthesis of new fluorescent bichromophoric compounds as ratiometric pH probes for intracellular measurements. Organic & Biomolecular Chemistry, 13 (28). pp. 7736-7749. ISSN 1477-0520Type
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Abstract
Three different bichromophoric compounds (1–3) containing an aminomethyl anthracene moiety linked
to a second chromophore (pyrene, 4-nitrobenzo-2-oxa-1,3-diazole (NBD) and dansyl) through a valinederived
pseudopeptidic ... [+]
Three different bichromophoric compounds (1–3) containing an aminomethyl anthracene moiety linked
to a second chromophore (pyrene, 4-nitrobenzo-2-oxa-1,3-diazole (NBD) and dansyl) through a valinederived
pseudopeptidic spacer have been prepared and their fluorescent properties studied. The results
obtained show that upon irradiation the photophysical behavior of these probes involves electronic
energy transfer from the excited anthracene to the second chromophore and also intramolecular photoinduced
electron transfer. The X-ray structure obtained for 3 reveals that the folding associated with the
pseudopeptidic spacer favours a close proximity of the two chromophores. The emissive response of 3 is
clearly dependent on the pH of the medium, hence this bichromophoric compound was shown to be an
excellent ratiometric pH fluorescent sensor. The emission intensity due to the anthracene moiety exhibits
a decrease at neutral–basic pH values that is concomitant with an increase in the intensity arising from
the dansyl fluorophore. These properties make this compound a good candidate for biological
pH sensing as has been confirmed by preliminary studies with RAW 264.7 macrophage cells imaged by
means of confocal fluorescence microscopy with an average pH estimation of 5.4–5.8 for acidic
organelles. [-]
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Organic & Biomolecular Chemistry, 2015, 13, 7736–7749Rights
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