Imine bond formation: A novel concept to incorporate peptide drugs in self-emulsifying drug delivery systems (SEDDS)

Dizdarević, Aida; Efiana, Nuri Ari; Phan, Thi Nhu Quynh; Matuszczak, Barbara; Bernkop‐Schnürch, Andreas

doi:10.1016/j.ejpb.2019.06.002

Cited by 12 publications

(9 citation statements)

References 31 publications

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“…However, in addition to antimicrobials, cinnamaldehyde has also shown some special advantages in the biomedical field, such as promoting cellular ROS production and inhibiting MDR strains. Moreover, cinnamaldehyde can also be conveniently applied to synthesize prodrugs with other drugs (e.g., Polymyxin B [ 99 ]) and stimuli-responsive polymers for drug delivery due to its high reactivity. Therefore, this review will focus on the applications of cinnamaldehyde-contained polymers in the biomedical field.…”

Section: The Applications In the Biomedical Fieldmentioning

confidence: 99%

Cinnamaldehyde-Contained Polymers and Their Biomedical Applications

Zhang

Liu

et al. 2023

Polymers

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Cinnamaldehyde, a natural product that can be extracted from a variety of plants of the genus Cinnamomum, exhibits excellent biological activities including antibacterial, antifungal, anti-inflammatory, and anticancer properties. To overcome the disadvantages (e.g., poor water solubility and sensitivity to light) or enhance the advantages (e.g., high reactivity and promoting cellular reactive oxygen species production) of cinnamaldehyde, cinnamaldehyde can be loaded into or conjugated with polymers for sustained or controlled release, thereby prolonging the effective action time of its biological activities. Moreover, when cinnamaldehyde is conjugated with a polymer, it can also introduce environmental responsiveness to the polymer through the form of stimuli-sensitive linkages between its aldehyde group and various functional groups of polymers. The environmental responsiveness provides the great potential of cinnamaldehyde-conjugated polymers for applications in the biomedical field. In this review, the strategies for preparing cinnamaldehyde-contained polymers are summarized and their biomedical applications are also reviewed.

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Section: The Applications In the Biomedical Fieldmentioning

confidence: 99%

Cinnamaldehyde-Contained Polymers and Their Biomedical Applications

Zhang

Liu

et al. 2023

Polymers

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“…At the same time, the molecule polarity (log P) was increased 69-fold. The release of polymyxin ranged from 45% to 81% within 16 h [130].…”

Section: Conjugatesmentioning

confidence: 99%

Polymyxin Delivery Systems: Recent Advances and Challenges

Dubashynskaya

Skorik

2020

Pharmaceuticals

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Polymyxins are vital antibiotics for the treatment of multiresistant Gram-negative ESKAPE pathogen infections. However, their clinical value is limited by their high nephrotoxicity and neurotoxicity, as well as their poor permeability and absorption in the gastrointestinal tract. This review focuses on various polymyxin delivery systems that improve polymyxin bioavailability and reduce drug toxicity through targeted and controlled release. Currently, the most suitable systems for improving oral, inhalation, and parenteral polymyxin delivery are polymer particles, liposomes, and conjugates, while gels, polymer fibers, and membranes are attractive materials for topical administration of polymyxin for the treatment of infected wounds and burns. In general, the application of these systems protects polymyxin molecules from the negative effects of both physiological and pathological factors while achieving higher concentrations at the target site and reducing dosage and toxicity. Improving the properties of polymyxin will be of great interest to researchers who are focused on developing antimicrobial drugs that show increased efficacy and safety.

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“…48,49 Dynamic covalent bonds are particularly attractive for the field of drug delivery, because these bonds can be broken under environment stimuli providing controlled drug release. 50 The most popular dynamic covalent bonds include hydrazone, 10,51 oxime, 52 imine, 53,54 disulfide, 55,56 boronate ester 57−59 etc. Recently, we have shown that lipophilic hydrazide LipoHD encapsulated inside NEs can form in situ dynamic hydrazone bonds with ketones, which ensure efficient capture of model cargo dye NRK and ketone drug doxorubicin.…”

Section: ■ Introductionmentioning

confidence: 99%

“…To realize an in situ reaction with an aldehyde, one could exploit dynamic covalent chemistry, which deals with dynamic bonds that form and disrupt reversibly under environmental control. , Dynamic covalent chemistry was successfully applied for designing intelligent materials with self-healing and adaptive properties. , Dynamic covalent bonds are particularly attractive for the field of drug delivery, because these bonds can be broken under environment stimuli providing controlled drug release . The most popular dynamic covalent bonds include hydrazone, , oxime, imine, , disulfide, , boronate ester − etc. Recently, we have shown that lipophilic hydrazide LipoHD encapsulated inside NEs can form in situ dynamic hydrazone bonds with ketones, which ensure efficient capture of model cargo dye NRK and ketone drug doxorubicin .…”

Section: Introductionmentioning

confidence: 99%

Controlled Release and Capture of Aldehydes by Dynamic Imine Chemistry in Nanoemulsions: From Delivery to Detoxification

Liu

Anton

Niko

et al. 2022

ACS Appl. Bio Mater.

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Current biomedical applications of nanocarriers are focused on drug delivery, where encapsulated cargo is released in the target tissues under the control of external stimuli. Here, we propose a very different approach, where the active toxic molecules are removed from biological tissues by the nanocarrier. It is based on the drug-sponge concept, where specific molecules are captured by the lipid nanoemulsion (NE) droplets due to dynamic covalent chemistry inside their oil core. To this end, we designed a highly lipophilic amine (LipoAmine) capable of reacting with a free cargo-aldehyde (fluorescent dye and 4-hydroxynonenal toxin) directly inside lipid NEs, yielding a lipophilic imine conjugate well encapsulated in the oil core. The formation of imine bonds was first validated using a push-pull pyrene aldehyde dye, which changes its emission color during the reaction. The conjugate formation was independently confirmed by mass spectrometry. As a result, LipoAmine-loaded NEs spontaneously loaded cargo-aldehydes, yielding formulations stable against leakage at pH 7.4, which can further release the cargo in a low pH range (4–6) in solutions and living cells. Using fluorescence microscopy, we showed that LipoAmine NEs can extract pyrene aldehyde dye from cells as well as from an epithelial tissue (chicken skin). Moreover, successful extraction from cells was also achieved for a highly toxic aliphatic aldehyde 4-hydroxynonenal, which allowed obtaining the proof of concept for detoxification of living cells. Taken together, these results show that the dynamic imine chemistry inside NEs can be used to develop detoxification platforms.

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Imine bond formation: A novel concept to incorporate peptide drugs in self-emulsifying drug delivery systems (SEDDS)

Cited by 12 publications

References 31 publications

Cinnamaldehyde-Contained Polymers and Their Biomedical Applications

Cinnamaldehyde-Contained Polymers and Their Biomedical Applications

Polymyxin Delivery Systems: Recent Advances and Challenges

Controlled Release and Capture of Aldehydes by Dynamic Imine Chemistry in Nanoemulsions: From Delivery to Detoxification

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