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A therapeutic keypad lock decoded in drug resistant cancer cells.

ABSTRACT: A molecular keypad lock that displays photodynamic activity when exposed to glutathione (GSH), esterase and light in the given order, is fabricated and its efficacy in drug resistant MCF7 cancer cells is investigated. The first two inputs are common drug resistant tumor markers. GSH reacts with the agent and shifts the absorption wavelength. Esterase separates the quencher from the structure, further activating the agent. After these sequential exposures, the molecular keypad lock is exposed to light and produces cytotoxic singlet oxygen. Among many possible combinations, only one 'key' can activate the agent, and initiate a photodynamic response. Paclitaxel resistant MCF7 cells are selectively killed. This work presents the first ever biological application of small molecular keypad locks.

SUBMITTER: Turkoglu G

PROVIDER: S-EPMC8293978 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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A therapeutic keypad lock decoded in drug resistant cancer cells.

Turkoglu Gulsen G Koygun Gozde Kayadibi GK Zafer Yurt Mediha Nur MN Pirencioglu Seyda Nur SN Erbas-Cakmak Sundus S

Chemical science 20210617 28

A molecular keypad lock that displays photodynamic activity when exposed to glutathione (GSH), esterase and light in the given order, is fabricated and its efficacy in drug resistant MCF7 cancer cells is investigated. The first two inputs are common drug resistant tumor markers. GSH reacts with the agent and shifts the absorption wavelength. Esterase separates the quencher from the structure, further activating the agent. After these sequential exposures, the molecular keypad lock is exposed to ...[more]

PMID: 34349948

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Project description:A novel thiazole phenol conjugate, 2-aminothiazolesalicylaldehyde (receptor1) was designed and synthesized for the first time through a single step process via Schiff base condensation reaction. The formation of receptor1 was confirmed by FTIR, 13C NMR, and 1H NMR. The IR spectra confirmed the presence of the aldimine formation. It is further supported by the proton NMR, showing the disappearance of aldehyde peaks and the formation of a new imine peak. This is further corroborated by the 13C NMR. The receptor1 complexing with various metal ions were studied through fluorescence spectroscopy showed its selectivity toward Fe2+ ion following a reverse photoinduced electron transfer (PET) process compared to all other potentially competing ions. The receptor1 was applied as a sensor to sense Fe2+ ion in water samples. The detection limit for Fe2+ ion in drinking water was substantially lower (0.003 µM) than the EPA (environmental protection agency) recommendation (5.37 M). The capability of receptor1 in recovering Fe2+ ion in bore water, tap water, and drinking water was up to 99.5%. The receptor1 was also used as a chelating ligand (receptor1) in molecular docking and it was assessed as a potential inhibitor of NUDT5, a silence hormone signaling for breast cancer. The test compound (PDB: 5NWH) showed good affinity toward the target receptor1 with the binding energy of - 5.23 kcal mol-1. Furthermore, the receptor1 showed excellent reversibility property on adding EDTA solution. Due to the marvelous reversible property, a molecular-scale sequential information processing circuit is designed for the multi-task behavior such as 'Writing-Reading-Erasing-Reading' in the form of binary logic gate. The consecutive addition of Fe2+ ion and EDTA solution to receptor1 paves a way for the construction of INHIBIT logic gate. Additionally, the receptor1 showed the mimicking behavior of molecular keypad lock.Supplementary informationThe online version contains supplementary material available at 10.1007/s11696-022-02373-z.

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A therapeutic keypad lock decoded in drug resistant cancer cells.

Publications

A therapeutic keypad lock decoded in drug resistant cancer cells.

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