Syntheses and kinetic studies of cyclisation-based self-immolative spacers

Huvelle, Steve; Alouane, Ahmed; Saux, Thomas Le; Jullien, Ludovic

doi:10.1039/c7ob00121e

Cited by 19 publications

(13 citation statements)

References 22 publications

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“…Dougherty and co-workers , studied analogs of 123 , an o -hydroxydihydrocinnamic acid derivative with a conformationally restrictive “trimethyl lock” that enables thermal uncaging and photoreduction to release alcohols and amines via a 1,6-rearrangement mechanism − (Scheme ). The UV-light-induced release of 2-nitrobenzyl-protected phenols to activate the trimethyl lock mechanism has been demonstrated previously. ,− …”

Section: Photorelease From Organic Photoactivatable Compoundsmentioning

confidence: 96%

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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Photoactivatable (alternatively, photoremovable, photoreleasable, or photocleavable) protecting groups (PPGs), also known as caged or photocaged compounds, are used to enable non-invasive spatiotemporal photochemical control over the release of species of interest. Recent years have seen the development of PPGs activatable by biologically and chemically benign visible and near-infrared (NIR) light. These long-wavelength-absorbing moieties expand the applicability of this powerful method and its accessibility to non-specialist users. This review comprehensively covers organic and transition metal-containing photoactivatable compounds (complexes) that absorb in the visible- and NIR-range to release various leaving groups and gasotransmitters (carbon monoxide, nitric oxide, and hydrogen sulfide). The text also covers visible- and NIR-light-induced photosensitized release using molecular sensitizers, quantum dots, and upconversion and second-harmonic nanoparticles, as well as release via photodynamic (photooxygenation by singlet oxygen) and photothermal effects. Release from photoactivatable polymers, micelles, vesicles, and photoswitches, along with the related emerging field of photopharmacology, is discussed at the end of the review.

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Section: Photorelease From Organic Photoactivatable Compoundsmentioning

confidence: 96%

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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“…Thed egradation process,d riven by ap ositive reaction entropy,t akes place through intramolecular reactions,m ainly electronic cascade in aromatic or pextended systems [5] or cyclization of nucleophilic species (e.g. amine, [6] phenol, [7] and thiol [8] groups,F igure 1B).…”

Section: Introductionmentioning

confidence: 99%

Fast Cyclization of a Proline‐Derived Self‐Immolative Spacer Improves the Efficacy of Carbamate Prodrugs

et al. 2020

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Self‐immolative (SI) spacers are sophisticated chemical constructs designed for molecular delivery or material degradation. We describe herein a (S)‐2‐(aminomethyl)pyrrolidine SI spacer that is able to release different types of anticancer drugs (possessing either a phenolic or secondary and tertiary hydroxyl groups) through a fast cyclization mechanism involving carbamate cleavage. The high efficiency of drug release obtained with this spacer was found to be beneficial for the in vitro cytotoxic activity of protease‐sensitive prodrugs, compared with a commonly used spacer of the same class. These findings expand the repertoire of degradation machineries and are instrumental for the future development of highly efficient delivery platforms.

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“…In contrast, self-immolative spacer groups based on continuous combinations (such as 1,8-elimination of naphthalene or 1,10-elimination of biphenyls) usually do not result in the release of drug groups because the high energy barrier destroys the aromaticity, and the repulsion of the hydrogen atom in adjacent biphenyl prevents the formation of the planar structure needed for electron rearrangement [ 172 ]. The cyclization reaction is based on alkyl chain or aromatic spacer groups [ 173 , 174 , 175 ]. Once the cleavage is triggered, the nucleophilic attack of carbonyl or electrophilic aliphatic carbon atoms could result in the cyclization of spacer groups.…”

Section: Stimulus-responsive Systemsmentioning

confidence: 99%

Stimulus-Responsive Nanomedicines for Disease Diagnosis and Treatment

Liu

Lovell

Zhang

et al. 2020

IJMS

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Stimulus-responsive drug delivery systems generally aim to release the active pharmaceutical ingredient (API) in response to specific conditions and have recently been explored for disease treatments. These approaches can also be extended to molecular imaging to report on disease diagnosis and management. The stimuli used for activation are based on differences between the environment of the diseased or targeted sites, and normal tissues. Endogenous stimuli include pH, redox reactions, enzymatic activity, temperature and others. Exogenous site-specific stimuli include the use of magnetic fields, light, ultrasound and others. These endogenous or exogenous stimuli lead to structural changes or cleavage of the cargo carrier, leading to release of the API. A wide variety of stimulus-responsive systems have been developed—responsive to both a single stimulus or multiple stimuli—and represent a theranostic tool for disease treatment. In this review, stimuli commonly used in the development of theranostic nanoplatforms are enumerated. An emphasis on chemical structure and property relationships is provided, aiming to focus on insights for the design of stimulus-responsive delivery systems. Several examples of theranostic applications of these stimulus-responsive nanomedicines are discussed.

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Syntheses and kinetic studies of cyclisation-based self-immolative spacers

Cited by 19 publications

References 22 publications

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Fast Cyclization of a Proline‐Derived Self‐Immolative Spacer Improves the Efficacy of Carbamate Prodrugs

Stimulus-Responsive Nanomedicines for Disease Diagnosis and Treatment

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