Supramolecular caging for cytosolic delivery of anionic probes

Fernández-Caro, Héctor; Lostalé‐Seijo, Irene; Martínez‐Calvo, Miguel; Mosquera, Jesús; Mascareñas, José L.; Montenegro, Javier

doi:10.1039/c9sc02906k

Cited by 21 publications

(7 citation statements)

References 40 publications

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“…The most important observation of our work is, however, that mitochondrial accumulation, promoted by a neutral carrier, enhanced the effect of the drug in several DCA-resistant cell lines. With this proof-of-concept, there is still plenty of room to improve drug efficacy by incorporating it in delivery nanoparticles [ 69 ] or supramolecular caging agents [ 73 ] and improving drug selectivity by reducing thiophene-associated toxicity by adding substitution radicals to the thiophene ring [ 38 ].…”

Section: Discussionmentioning

confidence: 99%

Chimeric Drug Design with a Noncharged Carrier for Mitochondrial Delivery

et al. 2021

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Recently, it was proposed that the thiophene ring is capable of promoting mitochondrial accumulation when linked to fluorescent markers. As a noncharged group, thiophene presents several advantages from a synthetic point of view, making it easier to incorporate such a side moiety into different molecules. Herein, we confirm the general applicability of the thiophene group as a mitochondrial carrier for drugs and fluorescent markers based on a new concept of nonprotonable, noncharged transporter. We implemented this concept in a medicinal chemistry application by developing an antitumor, metabolic chimeric drug based on the pyruvate dehydrogenase kinase (PDHK) inhibitor dichloroacetate (DCA). The promising features of the thiophene moiety as a noncharged carrier for targeting mitochondria may represent a starting point for the design of new metabolism-targeting drugs.

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Section: Discussionmentioning

confidence: 99%

Chimeric Drug Design with a Noncharged Carrier for Mitochondrial Delivery

et al. 2021

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“…8–11 A third approach builds on supramolecular interactions at the nanointerface that are generally reversible in mild conditions. 12–16 The development of stimuli-responsive supramolecular systems at the surface of nanoparticles has allowed the preparation of functional platforms for different biological applications. 17,18 In addition, nanoparticle functionalization by supramolecular interactions offers a versatile approach towards multicomponent integration into nanodevices.…”

Section: Introductionmentioning

confidence: 99%

Dynamic nanosurface reconfiguration by host–guest supramolecular interactions

Fernández-Caro

Méndez‐Ardoy²,

Montenegro

2022

Nanoscale

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“…For instance, anionic dyes such as fluorescein diffuse into the cytosol, while cationic fluorophores such as rhodamine and cyanine tend to accumulate in the mitochondria. [15][16][17] However, due to a low synthetic diversity in NIR fluorophores, it is still a challenge to develop biocompatible NIR probes with specific target localisation. This is a particular problem for those that use multiple fluorescent switching units for analysing complex and cooperative biological events.…”

Section: Introductionmentioning

confidence: 99%