2,2′Dithiodinicotinyl ligands: Key to more reactive thiomers

Menzel, Claudia; Silbernagl, Jennifer; Laffleur, Flavia; Leichner, Christina; Jelkmann, Max; Huck, Christian W.; Hussain, Shah; Bernkop‐Schnürch, Andreas

doi:10.1016/j.ijpharm.2016.03.010

Cited by 19 publications

(2 citation statements)

References 28 publications

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“…This augmented reactivity responds to the electron-withdrawing effect of the π-deficient ring, which promotes the lysis of asymmetric disulfide linkages, so that the formation of more stable disulfides, with electron-donating groups, is favorable. Hence, the thioamide 2-mercaptopyridine, 2-MNA, or 6-MNAm can be easily cleaved off [72].…”

Section: Thiol Oxidation and Disulfide Bond Formation: In Situ Gelling Propertiesmentioning

confidence: 99%

Thiolated-Polymer-Based Nanoparticles as an Avant-Garde Approach for Anticancer Therapies—Reviewing Thiomers from Chitosan and Hyaluronic Acid

Grosso

de-Paz

2021

Pharmaceutics

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Thiomers (or thiolated polymers) have broken through as avant-garde approaches in anticancer therapy. Their distinguished reactivity and properties, closely linked to their final applications, justify the extensive research conducted on their preparation and use as smart drug-delivery systems (DDSs). Multiple studies have demonstrated that thiomer-rich nanoformulations can overcome major drawbacks found when administering diverse active pharmaceutical ingredients (APIs), especially in cancer therapy. This work focuses on providing a complete and concise review of the synthetic tools available to thiolate cationic and anionic polymers, in particular chitosan (CTS) and hyaluronic acid (HA), respectively, drawing attention to the most successful procedures. Their chemical reactivity and most relevant properties regarding their use in anticancer formulations are also discussed. In addition, a variety of NP formation procedures are outlined, as well as their use in cancer therapy, particularly for taxanes and siRNA. It is expected that the current work could clarify the main synthetic strategies available, with their scope and drawbacks, as well as provide some insight into thiomer chemistry. Therefore, this review can inspire new research strategies in the development of efficient formulations for the treatment of cancer.

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Section: Thiol Oxidation and Disulfide Bond Formation: In Situ Gelling Propertiesmentioning

confidence: 99%

Thiolated-Polymer-Based Nanoparticles as an Avant-Garde Approach for Anticancer Therapies—Reviewing Thiomers from Chitosan and Hyaluronic Acid

Grosso

de-Paz

2021

Pharmaceutics

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“…For the analysis of the amount of immobilized −SH groups of these thiolated chitosans, Ellman’s reagent optionally with previous reduction of disulfide bonds with borohydride or iodometric titration can be used . Phadungcharoen et al, for instance, have conducted the Ellman’s assay via smartphone, providing an easy, fast, and reliable analysis of thiolated polymers without access to sophisticated equipment. …”

Section: Chitosan: Its Chemistry and Thiolationmentioning

confidence: 99%

Thiolated Chitosans: A Multi-talented Class of Polymers for Various Applications

2020

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Various properties of chitosan can be customized by thiolation for very specific needs in a wide range of application areas. Since the discovery of thiolated chitosans, many studies have proven their advantageous characteristics, such as adhesion to biological surfaces, adjustable cross-linking and swelling behavior, controllable drug release, permeation as well as cellular uptake enhancement, inhibition of efflux pumps and enzymes, complexation of metal ions, antioxidative properties, and radical scavenging activity. Simultaneously, these polymers remain biodegradable without increased toxicity. Within this Review, an overview about the different possibilities to covalently attach sulfhydryl ligands to the polymeric backbone of chitosan is given, and the resulting versatile physiochemical properties are discussed in detail. Furthermore, the broad spectrum of applications for thiolated chitosans in science and industry, ranging from their most advanced use in pharmaceutical and medical science over wastewater treatment to the impregnation of textiles, is addressed.

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