Tuning of hydrogen peroxide-responsive polymeric micelles of biodegradable triblock polycarbonates as a potential drug delivery platform with ratiometric fluorescence signaling

Fu, Yujian; Chen, Chun‐Yen; Chen, Chao‐Tsen

doi:10.1039/c5py01557j

Cited by 27 publications

(11 citation statements)

References 87 publications

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“…the non-proton transfer, normal emission). Such phototautomerism offers ample fundamental insights and can be specified with a barrierless process, a barrier induced, or a reversible process. − On the other hand, the diversification in the ESIPT mechanism renders different emission properties in terms of single, dual, and even multiple emissions that can be fine-tuned by varying the functionality, offering the versatility in applications such as in sensing, − bioimaging, − organic lasing, − and light-emitting diodes. ,,, …”

Section: Introductionmentioning

confidence: 99%

Chapter Open for the Excited-State Intramolecular Thiol Proton Transfer in the Room-Temperature Solution

et al. 2021

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We report here, for the first time, the experimental observation on the excited-state intramolecular proton transfer (ESIPT) reaction of the thiol proton in room-temperature solution. This phenomenon is demonstrated by a derivative of 3-thiolflavone (3TF), namely, 2-(4-(diethylamino)phenyl)-3mercapto-4H-chromen-4-one (3NTF), which possesses an SH•••O intramolecular H-bond (denoted by the dashed line) and has an S 1 absorption at 383 nm. Upon photoexcitation, 3NTF exhibits a distinctly red emission maximized at 710 nm in cyclohexane with an anomalously large Stokes shift of 12 230 cm −1 . Upon methylation on the thiol group, 3MeNTF, lacking the thiol proton, exhibits a normal Stokes-shifted emission at 472 nm. These, in combination with the computational approaches, lead to the conclusion of thiol-type ESIPT unambiguously. Further time-resolved study renders an unresolvable (<180 fs) ESIPT rate for 3NTF, followed by a tautomer emission lifetime of 120 ps. In sharp contrast to 3NTF, both 3TF and 3-mercapto-2-(4-(trifluoromethyl)phenyl)-4Hchromen-4-one (3FTF) are non-emissive. Detailed computational approaches indicate that all studied thiols undergo thermally favorable ESIPT. However, once forming the proton-transferred tautomer, the lone-pair electrons on the sulfur atom brings nonnegligible nπ* contribution to the S 1 ′ state (prime indicates the proton-transferred tautomer), for which the relaxation is dominated by the non-radiative deactivation. For 3NTF, the extension of π-electron delocalization by the diethylamino electron-donating group endows the S 1 ′ state primarily in the ππ* configuration, exhibiting the prominent tautomer emission. The results open a new chapter in the field of ESIPT, covering the non-canonical sulfur intramolecular H-bond and its associated ESIPT at ambient temperature.

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Section: Introductionmentioning

confidence: 99%

Chapter Open for the Excited-State Intramolecular Thiol Proton Transfer in the Room-Temperature Solution

et al. 2021

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“…Fu et al reported dual‐function theranostic micelles of amphiphilic triblock PCs that allow the possible targeted drug release and simultaneous ratiometric fluorescence sensing in response to H 2 O 2 . In this case, the disassembly and fluorescence behaviors of micelles are highly influenced by the structural features of the H 2 O 2 ‐reactive core‐forming HPO blocks . Moreover, Phan et al developed a new pH‐/temperature‐sensitive, biocompatible, biodegradable, and injectable hydrogel based on PEG‐ b ‐PACU copolymers for the sustained delivery of human growth hormone.…”

Section: Applicationsmentioning

confidence: 99%

Nanocomposites of Polymeric Biomaterials Containing Carbonate Groups: An Overview

Taraghi

Paszkiewicz

Grȩbowicz

et al. 2017

Macro Materials & Eng

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The modification of biomaterials using nanoadditives can lead to the development of novel materials for a wide variety of biomedical applications such as drug administration systems, tissue engineering, bioresistance coatings, and biomedical instruments. Moreover, a further improvement of mechanical and thermal properties of aforementioned biomaterials while maintaining their dimensional stability is a goal of major scientific researches. Aliphatic polycarbonates (APCs) containing carbonate groups such as poly(trimethylene carbonate), poly(propylene carbonate), poly(ethylene carbonate), poly(dimethyl trimethylene carbonate), etc., have become much more interesting compared to other biodegradable materials due to their unique physical and chemical properties. This review presents the effect of applying different kinds of nanoparticles (NPs) on the mechanical, thermal, and viscoelastic properties as well as dimensional stability and biocompatibility of APCs. The dispersion process of nanofillers within polymer matrices has been divided into two groups, solution and melt mixing techniques. Moreover, synthesis procedures of APC loaded NPs for drug delivery systems and electrospinning of nanofiber mats have also been reviewed. In order to clarify the effect of NPs on the overall characteristics of the APC biomaterials, the detailed mechanism of improving process have been extensively discussed.

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“…By introducing host-guest interactions in C3Ms, the stability against salt and competing cyclodextrin could be adjusted by finely tuning the charge of the adamantane guest (15). Here, we selected ferrocene as guest for its well-known 1:1 inclusion complex with β-CD, with an association constant (k a ) around 4.1 10 3 M −1 (in its reduced form) (21)(22)(23)(24)(25)(26) and for its responsivity towards mild oxidants, such as FeCl 3 , AgNO 3 , I 2 (27)(28)(29) or H 2 O 2 (16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35). The oxidation reaction of ferrocene to ferrocenium (Fc + ) causes consequently the dissociation of the Fc + from the β-CD (k a 15 M −1 ).…”

Section: Introductionmentioning

confidence: 99%

Oxidant-responsive ferrocene-based cyclodextrin complex coacervate core micelles

Facciotti

Saggiomo

Hurne

et al. 2019

Supramolecular Chemistry

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Coacervate-core micelles are considered promising materials for several applications, from catalysis to drug delivery. However, oxidant-responsive coacervate-core micelles, able to undergo structural changes upon specific oxidation stimuli, are not well reported. Here, we present a novel ferrocene-dipicolinic acid derivative as redox-responsive subcomponent to be incorporated in cyclodextrin-based coacervate core micelles, C4Ms, with tuneable core structure and responsiveness towards H 2 O 2 treatment. The Fc-C4Ms are formed combining three orthogonal supramolecular interactions, namely (i) metal-to-ligand coordination between europium(III) ions and dipicolinic acid molecules, (ii) host-guest interaction between beta cyclodextrins and ferrocenes and (iii) electrostatic coacervation interaction. The micelle stability against oxidation can be controlled by varying three main parameters: (a) the core-unit structure, from monomeric metal complexes to supramolecular oligomers, (b) the H 2 O 2 equivalents and c) the ratio between redoxresponsive and non-redox-responsive bislinker. The H 2 O 2 -responsive ferrocene-based systems might have an interesting application, e.g. reactive oxygen species-mediated drug delivery.

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Tuning of hydrogen peroxide-responsive polymeric micelles of biodegradable triblock polycarbonates as a potential drug delivery platform with ratiometric fluorescence signaling

Abstract: Two micelles of amphiphilic triblock polycarbonates with different H2O2-reactive core-forming blocks manifest disparate H2O2-induced disaggregation behaviors of micelles.

Cited by 27 publications

References 87 publications

Chapter Open for the Excited-State Intramolecular Thiol Proton Transfer in the Room-Temperature Solution

Chapter Open for the Excited-State Intramolecular Thiol Proton Transfer in the Room-Temperature Solution

Nanocomposites of Polymeric Biomaterials Containing Carbonate Groups: An Overview

Oxidant-responsive ferrocene-based cyclodextrin complex coacervate core micelles

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