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Near-infrared fluorescent probes with BODIPY donors and rhodamine and merocyanine acceptors for ratiometric determination of lysosomal pH variance.

ABSTRACT: Three fluorescent probes have been developed by conjugating three different BODIPY donors to rhodamine and merocyanine acceptors for ratiometric determination of lysosomal pH variations. Probe A consists of a 1,3,5,7-tetramethyl-BODIPY donor and a near-infrared rhodamine acceptor bearing a lysosome-targeting morpholine residue. Probe B is composed of a 3,5-dimethyl-BODIPY donor and a near-infrared rhodamine acceptor modified with an o-phenylenediamine residue. Probe C contains a 3-styrene-functionalized BODIPY donor with longer wavelength emission and a near-infrared merocyanine acceptor containing a morpholine residue. Under neutral or basic pH conditions, the probes only show fluorescence from the BODIPY donors under BODIPY excitation because the rhodamine and merocyanine acceptors maintain closed spirolactam configurations. However, excitation at BODIPY absorption wavelengths concomitant with gradual pH decrease results in fluorescence decreases with the BODIPY donors and fluorescence increases from the rhodamine and merocyanine acceptors due to through-bond energy transfer from the donors to the acceptors. This is because the spirolactam ring opens under more acidic conditions and fluorescence of the acceptors results from significantly improved ?-conjugation. These experimental results are substantiated with theoretical calculations on models of the different probes. The probes have all been used to determine lysosome pH variations in HeLa cells. Probe B was further utilized to successfully detect pH fluctuations in HeLa cells under oxidative stress and with treatment of NH4Cl and chloroquine.

SUBMITTER: Xia S

PROVIDER: S-EPMC6730546 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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Near-infrared fluorescent probes with BODIPY donors and rhodamine and merocyanine acceptors for ratiometric determination of lysosomal pH variance.

Xia Shuai S Fang Mingxi M Wang Jianbo J Bi Jianheng J Mazi Wafa W Zhang Yibin Y Luck Rudy L RL Liu Haiying H

Sensors and actuators. B, Chemical 20190504

Three fluorescent probes have been developed by conjugating three different BODIPY donors to rhodamine and merocyanine acceptors for ratiometric determination of lysosomal pH variations. Probe A consists of a 1,3,5,7-tetramethyl-BODIPY donor and a near-infrared rhodamine acceptor bearing a lysosome-targeting morpholine residue. Probe B is composed of a 3,5-dimethyl-BODIPY donor and a near-infrared rhodamine acceptor modified with an o-phenylenediamine residue. Probe C ...[more]

PMID: 31496551

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Project description:It is well-known that for an electron transfer reaction, the electron-donating ability of electron donors and the electron-accepting ability of electron acceptors can be quantitatively described by the oxidation potential of electron donors and the reduction potential of electron acceptors. However, for an electron transfer reaction, the electron-donating activity of electron donors and the electron-accepting activity of electron acceptors cannot be quantitatively described by a characteristic parameter of electron donors and a characteristic parameter of electron acceptors till now. In this paper, a characteristic activity parameter of electron donors and electron acceptors named as their thermo-kinetic parameter is proposed to quantify the electron-donating activity of electron donors and the electron-accepting activity of electron acceptors in electron transfer reactions. At the same time, the thermo-kinetic parameter values of 70 well-known electron donors and the corresponding 70 conjugated electron acceptors in acetonitrile at 298 K are determined. The activation free energies of 4900 typical electron transfer reactions in acetonitrile at 298 K are estimated according to the thermo-kinetic parameter values of 70 electron donors and 70 conjugated electron acceptors, and the estimated results have received good verification of the corresponding independent experimental measurements. The physical meaning of the thermo-kinetic parameter is examined. The relationship of the thermo-kinetic parameter with the corresponding redox potential as well as the relationship of the activation free energy with the corresponding thermodynamic driving force of electron transfer reactions is examined. The results show that the observed relationships between the thermo-kinetic parameters and the redox potentials as well as the observed relationships between the activation free energy and the thermodynamic driving force depend on the choice of electron donors and electron acceptors as well as the electron transfer reactions. The greatest contribution of this paper is to realize the symmetry and unification of kinetic equations and the corresponding thermodynamic equations of electron transfer reactions.

Dataset Information

Near-infrared fluorescent probes with BODIPY donors and rhodamine and merocyanine acceptors for ratiometric determination of lysosomal pH variance.

Publications

Near-infrared fluorescent probes with BODIPY donors and rhodamine and merocyanine acceptors for ratiometric determination of lysosomal pH variance.

Similar Datasets

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