Fluorescent macrocyclic probes with pendant functional groups as markers of acidic organelles within live cells

Prashant D. Wadhavane; M. Ángeles Izquierdo; Dennis Lutters; M. Isabel Burguete; MJ Marin; David A. Russell; Francisco Galindo; Santiago V. Luis

doi:10.1039/c3ob41773e

Fluorescent macrocyclic probes with pendant functional groups as markers of acidic organelles within live cells

Prashant D. Wadhavane, M. Ángeles Izquierdo, Dennis Lutters, M. Isabel Burguete, MJ Marin, David A. Russell, Francisco Galindo, Santiago V. Luis

Chemistry of Materials and Catalysis

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

A new family of acidity sensitive fluorescent macrocycles has been synthesized and fully characterized. Their photophysical properties including emission quantum yield and fluorescence lifetime have been determined. The acid–base properties of the new molecules can be tuned by the incorporation of pendant functional groups. The nature of such functional groups (carboxylic acid or ester) influences dramatically the pKa of the probes, two compounds of which exhibit low values. Preliminary intracellular studies using confocal microscopy together with emission spectra of the probes from the cellular environment have shown that the synthesized fluorescent macrocycles mark the acidic organelles of RAW 264.7 macrophage cells.

Original language	English
Pages (from-to)	823-831
Number of pages	9
Journal	Organic & Biomolecular Chemistry
Volume	12
DOIs	https://doi.org/10.1039/c3ob41773e
Publication status	Published - 1 Jan 2014

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10.1039/c3ob41773e

Cite this

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title = "Fluorescent macrocyclic probes with pendant functional groups as markers of acidic organelles within live cells",

abstract = "A new family of acidity sensitive fluorescent macrocycles has been synthesized and fully characterized. Their photophysical properties including emission quantum yield and fluorescence lifetime have been determined. The acid–base properties of the new molecules can be tuned by the incorporation of pendant functional groups. The nature of such functional groups (carboxylic acid or ester) influences dramatically the pKa of the probes, two compounds of which exhibit low values. Preliminary intracellular studies using confocal microscopy together with emission spectra of the probes from the cellular environment have shown that the synthesized fluorescent macrocycles mark the acidic organelles of RAW 264.7 macrophage cells.",

author = "Wadhavane, {Prashant D.} and Izquierdo, {M. {\'A}ngeles} and Dennis Lutters and Burguete, {M. Isabel} and MJ Marin and Russell, {David A.} and Francisco Galindo and Luis, {Santiago V.}",

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doi = "10.1039/c3ob41773e",

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T1 - Fluorescent macrocyclic probes with pendant functional groups as markers of acidic organelles within live cells

AU - Wadhavane, Prashant D.

AU - Izquierdo, M. Ángeles

AU - Lutters, Dennis

AU - Burguete, M. Isabel

AU - Marin, MJ

AU - Russell, David A.

AU - Galindo, Francisco

AU - Luis, Santiago V.

PY - 2014/1/1

Y1 - 2014/1/1

N2 - A new family of acidity sensitive fluorescent macrocycles has been synthesized and fully characterized. Their photophysical properties including emission quantum yield and fluorescence lifetime have been determined. The acid–base properties of the new molecules can be tuned by the incorporation of pendant functional groups. The nature of such functional groups (carboxylic acid or ester) influences dramatically the pKa of the probes, two compounds of which exhibit low values. Preliminary intracellular studies using confocal microscopy together with emission spectra of the probes from the cellular environment have shown that the synthesized fluorescent macrocycles mark the acidic organelles of RAW 264.7 macrophage cells.

AB - A new family of acidity sensitive fluorescent macrocycles has been synthesized and fully characterized. Their photophysical properties including emission quantum yield and fluorescence lifetime have been determined. The acid–base properties of the new molecules can be tuned by the incorporation of pendant functional groups. The nature of such functional groups (carboxylic acid or ester) influences dramatically the pKa of the probes, two compounds of which exhibit low values. Preliminary intracellular studies using confocal microscopy together with emission spectra of the probes from the cellular environment have shown that the synthesized fluorescent macrocycles mark the acidic organelles of RAW 264.7 macrophage cells.

U2 - 10.1039/c3ob41773e

DO - 10.1039/c3ob41773e

M3 - Article

VL - 12

SP - 823

EP - 831

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

ER -