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  1. Article ; Online: Photoinduced Release of a Chemical Fuel for Acid-Base-Operated Molecular Machines.

    Biagini, Chiara / Di Pietri, Flaminia / Mandolini, Luigi / Lanzalunga, Osvaldo / Di Stefano, Stefano

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2018  Volume 24, Issue 40, Page(s) 10122–10127

    Abstract: Back and forth motions of the acid-base-operated molecular switch 1 are photo-controlled by irradiation of a solution, which also contains the photolabile pre-fuel 4. The photo-stimulated deprotection of the pre-fuel produces controlled amounts of acid 2, ...

    Abstract Back and forth motions of the acid-base-operated molecular switch 1 are photo-controlled by irradiation of a solution, which also contains the photolabile pre-fuel 4. The photo-stimulated deprotection of the pre-fuel produces controlled amounts of acid 2, the base-promoted decarboxylation of which fuels the back and forth motions of the Sauvage-type [2]-catenane-based molecular switch. Because switch 1 and pre-fuel 4 do not interact in the absence of irradiation, an excess of the latter with respect to 1 can be added to the solution from the beginning. In principle, photocontrol of the back and forth motions of any molecular machine, the operation of which is guided by protonation/deprotonation, could be attained by use of pre-fuel 4, or of any other protected acid that undergoes deprotection by irradiation with light at a proper wavelength, followed by decarboxylation under conveniently mild conditions.
    Language English
    Publishing date 2018-06-12
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.201800474
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Turning Donepezil into a Multi-Target-Directed Ligand through a Merging Strategy.

    Perone, Rosaria / Albertini, Claudia / Uliassi, Elisa / Di Pietri, Flaminia / de Sena Murteira Pinheiro, Pedro / Petralla, Sabrina / Rizzardi, Nicola / Fato, Romana / Pulkrabkova, Lenka / Soukup, Ondrej / Tramarin, Anna / Bartolini, Manuela / Bolognesi, Maria Laura

    ChemMedChem

    2020  Volume 16, Issue 1, Page(s) 187–198

    Abstract: Thanks to the widespread use and safety profile of donepezil (1) in the treatment of Alzheimer's disease (AD), one of the most widely adopted multi-target-directed ligand (MTDL) design strategies is to modify its molecular structure by linking a second ... ...

    Abstract Thanks to the widespread use and safety profile of donepezil (1) in the treatment of Alzheimer's disease (AD), one of the most widely adopted multi-target-directed ligand (MTDL) design strategies is to modify its molecular structure by linking a second fragment carrying an additional AD-relevant biological property. Herein, supported by a proposed combination therapy of 1 and the quinone drug idebenone, we rationally designed novel 1-based MTDLs targeting Aβ and oxidative pathways. By exploiting a bioisosteric replacement of the indanone core of 1 with a 1,4-naphthoquinone, we ended up with a series of highly merged derivatives, in principle devoid of the "physicochemical challenge" typical of large hybrid-based MTDLs. A preliminary investigation of their multi-target profile identified 9, which showed a potent and selective butyrylcholinesterase inhibitory activity, together with antioxidant and antiaggregating properties. In addition, it displayed a promising drug-like profile.
    MeSH term(s) Acetylcholinesterase/chemistry ; Acetylcholinesterase/metabolism ; Alzheimer Disease/drug therapy ; Amyloid beta-Peptides/antagonists & inhibitors ; Amyloid beta-Peptides/metabolism ; Antioxidants/chemistry ; Antioxidants/metabolism ; Antioxidants/pharmacology ; Blood-Brain Barrier/diagnostic imaging ; Blood-Brain Barrier/metabolism ; Cell Line, Tumor ; Cell Survival/drug effects ; Cholinesterase Inhibitors/chemistry ; Cholinesterase Inhibitors/metabolism ; Cholinesterase Inhibitors/pharmacology ; Cholinesterase Inhibitors/therapeutic use ; Donepezil/chemistry ; Donepezil/metabolism ; Donepezil/pharmacology ; Donepezil/therapeutic use ; Drug Design ; Humans ; Indans/chemistry ; Ligands ; Neuroprotective Agents/chemistry ; Neuroprotective Agents/metabolism ; Neuroprotective Agents/pharmacology ; Neuroprotective Agents/therapeutic use ; Oxidative Stress/drug effects ; Protein Aggregates/drug effects ; Structure-Activity Relationship
    Chemical Substances Amyloid beta-Peptides ; Antioxidants ; Cholinesterase Inhibitors ; Indans ; Ligands ; Neuroprotective Agents ; Protein Aggregates ; Donepezil (8SSC91326P) ; indacrinone (B926Y9U4QN) ; Acetylcholinesterase (EC 3.1.1.7)
    Language English
    Publishing date 2020-08-31
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2218496-X
    ISSN 1860-7187 ; 1860-7179
    ISSN (online) 1860-7187
    ISSN 1860-7179
    DOI 10.1002/cmdc.202000484
    Database MEDical Literature Analysis and Retrieval System OnLINE

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