A New Glutathione-Cleavable Theranostic for Photodynamic Therapy Based on Bacteriochlorin e and Styrylnaphthalimide Derivatives
Open Access
- 8 December 2022
- journal article
- research article
- Published by MDPI AG in Biosensors
- Vol. 12 (12), 1149
- https://doi.org/10.3390/bios12121149
Abstract
Herein, we report a new conjugate BChl–S–S–NI based on the second-generation photosensitizer bacteriochlorin e6 (BChl) and a 4-styrylnaphthalimide fluorophore (NI), which is cleaved into individual functional fragments in the intracellular medium. The chromophores in the conjugate were cross-linked by click chemistry via a bis(azidoethyl)disulfide bridge which is reductively cleaved by the intracellular enzyme glutathione (GSH). A photophysical investigation of the conjugate in solution by using optical spectroscopy revealed that the energy transfer process is realized with high efficiency in the conjugated system, leading to the quenching of the emission of the fluorophore fragment. It was shown that the conjugate is cleaved by GSH in solution, which eliminates the possibility of energy transfer and restores the fluorescence of 4-styrylnaphthalimide. The photoinduced activity of the conjugate and its imaging properties were investigated on the mouse soft tissue sarcoma cell line S37. Phototoxicity studies in vitro show that the BChl–S–S–NI conjugate has insignificant dark cytotoxicity in the concentration range from 15 to 20,000 nM. At the same time, upon photoexcitation, it exhibits high photoinduced activity.Keywords
Funding Information
- Russian Federation President Grant for young scientists (MK-4878.2021.1.3.)
- RSF project (21-73-20158)
This publication has 42 references indexed in Scilit:
- Synthesis, Photophysical, Electrochemical, Tumor-Imaging, and Phototherapeutic Properties of Purpurinimide-N-substituted Cyanine Dyes Joined with Variable Lengths of LinkersBioconjugate Chemistry, 2011
- The role of porphyrin chemistry in tumor imaging and photodynamic therapyChemical Society Reviews, 2010
- Glutathione: A key player in autoimmunityAutoimmunity Reviews, 2009
- Intramolecular energy transfer in rhodamine–phthalocyanine conjugatesJournal of Photochemistry and Photobiology A: Chemistry, 2008
- Glutathione-Mediated Delivery and Release Using Monolayer Protected Nanoparticle CarriersJournal of the American Chemical Society, 2006
- Photophysical Properties of Coumarin-152 and Coumarin-481 Dyes: Unusual Behavior in Nonpolar and in Higher Polarity SolventsThe Journal of Physical Chemistry A, 2003
- Water-soluble 1,3-diphenylisobenzofuran derivatives. Synthesis and evaluation as singlet molecular oxygen acceptors for biological systemsJournal of Photochemistry and Photobiology A: Chemistry, 1996
- Spin‐Statistical Factors in Diffusion‐Controlled ReactionsPublished by Wiley ,1988
- Determination of quantum yields of fluorescence by optimizing the fluorescence intensityAnalytical Chemistry, 1983
- Radiationless decay of singlet molecular oxygen in solution. Experimental and theoretical study of electronic-to-vibrational energy transferJournal of the American Chemical Society, 1972