One-pot one-step synthesis of a photo-cleavable cross-linker via Passerini reaction for fabrication of responsive polymeric particles

Deveci, Gözde; Kahveci, Muhammet U.

doi:10.1007/s00289-018-2449-0

Cited by 7 publications

(5 citation statements)

References 38 publications

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“…In a recent study, PMMA-based photo-responsive microspheres and nanospheres were prepared using acrylate cross linkers that were made with two o-nitrobenzylester moieties. The formulation showed photo response at 366 nm, suggesting its wide range of application in constructing drug delivery and imaging formulations [ 192 ]. Another widely used linker to design photo-responsive systems is coumarin.…”

Section: Stimuli-responsive Polymeric Nanocarriers For Drug and Gmentioning

confidence: 99%

Stimuli-Responsive Polymeric Nanocarriers for Drug Delivery, Imaging, and Theragnosis

et al. 2020

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In the past few decades, polymeric nanocarriers have been recognized as promising tools and have gained attention from researchers for their potential to efficiently deliver bioactive compounds, including drugs, proteins, genes, nucleic acids, etc., in pharmaceutical and biomedical applications. Remarkably, these polymeric nanocarriers could be further modified as stimuli-responsive systems based on the mechanism of triggered release, i.e., response to a specific stimulus, either endogenous (pH, enzymes, temperature, redox values, hypoxia, glucose levels) or exogenous (light, magnetism, ultrasound, electrical pulses) for the effective biodistribution and controlled release of drugs or genes at specific sites. Various nanoparticles (NPs) have been functionalized and used as templates for imaging systems in the form of metallic NPs, dendrimers, polymeric NPs, quantum dots, and liposomes. The use of polymeric nanocarriers for imaging and to deliver active compounds has attracted considerable interest in various cancer therapy fields. So-called smart nanopolymer systems are built to respond to certain stimuli such as temperature, pH, light intensity and wavelength, and electrical, magnetic and ultrasonic fields. Many imaging techniques have been explored including optical imaging, magnetic resonance imaging (MRI), nuclear imaging, ultrasound, photoacoustic imaging (PAI), single photon emission computed tomography (SPECT), and positron emission tomography (PET). This review reports on the most recent developments in imaging methods by analyzing examples of smart nanopolymers that can be imaged using one or more imaging techniques. Unique features, including nontoxicity, water solubility, biocompatibility, and the presence of multiple functional groups, designate polymeric nanocues as attractive nanomedicine candidates. In this context, we summarize various classes of multifunctional, polymeric, nano-sized formulations such as liposomes, micelles, nanogels, and dendrimers.

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Section: Stimuli-responsive Polymeric Nanocarriers For Drug and Gmentioning

confidence: 99%

Stimuli-Responsive Polymeric Nanocarriers for Drug Delivery, Imaging, and Theragnosis

et al. 2020

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“…Notably, the photodegradable groups involved in these carriers are o -nitrobenzyl ester and coumarin, which can be degraded under UV and visible illumination and whose light-responsive wavelengths can be modulated through the substitution of the aldehyde moieties. Deveci et al [ 32 ] achieved the synthesis of a light cleavable acrylate-based crosslinker featuring o -nitrobenzyl ester units through a singular step using the P-3CR. Subsequently, they produced poly(methyl methacrylate) microspheres and nanospheres utilizing the crosslinker via suspension and miniemulsion polymerization.…”

Section: Introductionmentioning

confidence: 99%

A Facile Synthetic Approach to UV-Degradable Hydrogels

Li,

Wang,

Jiang

et al. 2023

Polymers

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Light-degradable hydrogels have a wide range of application prospects in the field of biomedicine. However, the provision of a facile synthetic approach to light-degradable hydrogels under mild conditions remains a challenge for researchers. To surmount this challenge, a facile synthetic approach to UV-degradable hydrogels is demonstrated in this manuscript. Initially, an UV-degradable crosslinker (UVDC) having o-nitrobenzyl ester groups was synthesized in a single step through the employment of the Passerini three-component reaction (P-3CR). Both 1H NMR and MS spectra indicated the successful synthesis of high-purity UVDC, and it was experimentally demonstrated that the synthesized UVDC was capable of degradation under 368 nm light. Furthermore, this UVDC was mixed with 8-arm PEG-thiol (sPEG20k-(SH)8) to promptly yield an UV-degradable hydrogel through a click reaction. The SEM image of the fabricated hydrogel exhibits the favorable crosslinking network of the hydrogel, proving the successful synthesis of the hydrogel. After continuous 368 nm irradiation, the hydrogel showed an obvious gel-sol transition, which demonstrates that the hydrogel possesses a desirable UV-degradable property. In summary, by utilizing solely a two-step reaction devoid of catalysts and hazardous raw materials, UV-degradable hydrogels can be obtained under ambient conditions, which greatly reduces the difficulty of synthesizing light-degradable hydrogels. This work extends the synthetic toolbox for light-degradable hydrogels, enabling their accelerated development.

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“…Depending on the substituents of the tetrazole, the required wavelength for the photoreaction can be readily fine tuned within the UV- and the visible-light range. − Thus, the polymer can be modified with various functionalities in a precise fashion by adjusting the respective wavelength. While such a strategy is appealing, the synthetic approach toward light-responsive polymers is challenging and possible only in a multistep fashion, often accompanied by complex monomer or polymer synthesis. ,− …”

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confidence: 99%

“…Therefore, peak deconvolution of the SEC trace was conducted, 45,46 giving the actual M n of P4 (Figure S6 in the SI). On the other hand, 3,4,5-trifluoroaniline (TFA) was employed, evidencing the photochemical postmodification of P2 via 1 H and 19 F NMR spectroscopy (Figures S7−S8 in the SI), affording the respective polymer P5 (refer to Scheme 1). Since both a UVand a vis-sensitive tetrazole moiety are incorporated into P3, the postmodification can be conducted in a λ-orthogonal manner.…”

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confidence: 99%

“…First, P3 was irradiated at λ em = 410−420 nm to exclusively modify the vis-responsive units (P6) with TFA, while subsequent exposure to UV light (λ max = 320 nm) in the presence of mPEG-Mal led to the modification of the UVresponsive units (P7) (refer to Figure 2A). The successful λorthogonal modification can be clearly detected via 1 H and 19 F NMR analysis (Figure 2B Possibly, hydrogen bonding and coiling effects might be responsible due to the peptide-mimicking structures of the polymers. Due to the modification of P6 with a second polymer (mPEG-Mal), the successful photoreaction yielding P7 should be evident via SEC analysis.…”

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confidence: 99%

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Passerini Multicomponent Reactions Enabling Self-Reporting Photosensitive Tetrazole Polymers

2021

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We introduce the synthesis of photosensitive tetrazole monomers via Passerini multicomponent reactions (MCRs). We exploit the MCR's tolerance toward various functional groups under mild, catalyst-free conditions in a onepot reaction setup to generate tetrazole-containing monomers featuring a methacrylic moiety, which enables their subsequent reversible addition−fragmentation chain transfer (RAFT) polymerization. By employing tetrazoles with either a 4-methoxy phenyl or a pyrene substituent, further modifications of the polymers in a wavelength-orthogonal, self-reporting fashion upon irradiation with either UV or visible light become possible.

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One-pot one-step synthesis of a photo-cleavable cross-linker via Passerini reaction for fabrication of responsive polymeric particles

Cited by 7 publications

References 38 publications

Stimuli-Responsive Polymeric Nanocarriers for Drug Delivery, Imaging, and Theragnosis

Stimuli-Responsive Polymeric Nanocarriers for Drug Delivery, Imaging, and Theragnosis

A Facile Synthetic Approach to UV-Degradable Hydrogels

Passerini Multicomponent Reactions Enabling Self-Reporting Photosensitive Tetrazole Polymers

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