Entirely S-Protected Thiolated Silicone: A Novel Hydrophobic Mucoadhesive and Skin Adhesive

Fürst, Andrea; Baus, Randi Angela; Lupo, Noemi; Bernkop‐Schnürch, Andreas

doi:10.1016/j.xphs.2019.04.003

Cited by 11 publications

(9 citation statements)

References 31 publications

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“…Mucoadhesion is a complex process that involves in the case of thiomers, non-covalent and covalent interactions [ 22 ]. In this regard, the interpenetration of polymeric chains is of particular importance, since a higher degree of interpenetration will certainly lead to increased non-covalent/covalent interactions of polymers with mucus resulting in higher mucoadhesion.…”

Section: Discussionmentioning

confidence: 99%

“…Rheological investigations were performed to determine the viscoelasticity of s -protected thiolated PAA conjugates as described previously by our research group [ 22 ]. Experiments were performed using Haake Mars Rheometer (Thermo Scientific™ HAAKE™ MARS™ rheometer, Thermo Fisher Scientific, Karlsruhe, Germany; Rotor C35/1°, D = 35 mm) with shear stress at a range of 0.5–500 Pa.…”

Section: Methodsmentioning

confidence: 99%

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Less Reactive Thiol Ligands: Key towards Highly Mucoadhesive Drug Delivery Systems

et al. 2020

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As less reactive s-protected thiomers can likely interpenetrate the mucus gel layer to a higher extent before getting immobilized via disulfide bond formation with mucins, it was the aim of this study to develop a novel type of s-protected thiomer based on the less reactive substructure cysteine-N-acetyl cysteine (Cys-NAC) in order to obtain improved mucoadhesive properties. For this purpose, two types of s-protected thiomers, polyacrylic acid-cysteine-mercaptonicotinic acid (PAA-Cys-MNA) and polyacrylic acid-cysteine-N-acetyl cysteine (PAA-Cys-NAC), were synthesized and characterized by Fourier-transform infrared spectroscopy (FT-IR) and the quantification of attached disulfide ligands. The viscosity of both products was measured in the presence of NAC and mucus. Both thiomers were also evaluated regarding swelling behavior, tensile studies and retention time on the porcine intestinal mucosa. The FT-IR spectra confirmed the successful attachment of Cys-MNA and Cys-NAC ligands to PAA. The number of attached sulfhydryl groups was in the range of 660–683 µmol/g. The viscosity of both s-protected thiomers increased due to the addition of increasing amounts of NAC. The viscosity of the mucus increased in the presence of 1% PAA-Cys-MNA and PAA-Cys-NAC 5.6- and 10.9-fold, respectively, in comparison to only 1% PAA. Both s-protected thiomers showed higher water uptake than unmodified PAA. The maximum detachment force (MDF) and the total work of adhesion (TWA) increased in the case of PAA-Cys-MNA up to 1.4- and 1.6-fold and up to 2.4- and 2.8-fold in the case of PAA-Cys-NAC. The retention of PAA, PAA-Cys-MNA, and PAA-Cys-NAC on porcine intestinal mucosa was 25%, 49%, and 76% within 3 h, respectively. The results of this study provide evidence that less reactive s-protected thiomers exhibit higher mucoadhesive properties than highly reactive s-protected thiomers.

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Less Reactive Thiol Ligands: Key towards Highly Mucoadhesive Drug Delivery Systems

et al. 2020

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“…In the silicone-MPA spectrum at the 1015 cm −1 wave number, a doublet of Si–O–Si stretching vibrations occurred that end at ca. 800 cm −1 , where the vibrations of the –CH 3 group and Si–C stretching vibrations can be observed [ 32 , 33 ].…”

Section: Resultsmentioning

confidence: 99%

“…Despite the data found in the literature concerning the great potential of thiolated silicon oils as bioadhesive substances, they have various shortcomings such as a cationic nature and limited stability against oxidation [ 32 ]. Polycations, despite their versatile and widespread use as drug delivery systems, are known to be hemotoxic via interacting with a cell membrane since overall polyanionic barriers disturb the membrane structure and function.…”

Section: Discussionmentioning

confidence: 99%

Thiolated Silicone Oils as New Components of Protective Creams in the Prevention of Skin Diseases

et al. 2021

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This work investigates the possibility of using thiolated silicone oils as new components in protective creams and their impact on the efficacy of these products. Thiolated silicone oils were synthesized by amide bond formation between primary amino groups of poly17dimethylsiloxane-co-(3-aminopropyl)-methylsiloxane] and carboxylic groups of thiol ligand (3-mercaptopropionic acid) with carbodiimide as a coupling agent. To evaluate and compare the properties of these kinds of thiomers, three different emulsion o/w types were obtained. Emulsion E1 contained methyl silicone oil, E2 poly[dimethylsiloxane-co-(3-aminopropyl)-methylsiloxane], and E3 thiolated silicone oil (silicone-MPA), respectively. Physicochemical properties, including pH, conductivity, droplet size distribution, viscosity, and stability, were assessed. The efficacy of barrier creams in the prevention of occupational skin diseases depends on their mechanical and rheological properties. Thus, the method which imitates the spreadability conditions on the skin and how structure reconstruction takes places was performed. We also investigated textural profile, bioadhesion, protection against water and detergents, and water vapor permeability. Emulsion E3 was characterized by beneficial occlusion, spreadability, and adhesion properties. These features with prolonged residence time on the skin can make designed barrier creams more preferable for consumers.

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“…The mucoadhesive properties of thiolated synthetic polymers have been studied, also. Synthetic polymer backbones for this purpose include: poly(acrylic acid) [ 68 , 69 ], poly(methacrylate) [ 70 ], poly(acrylamide) [ 71 ], silicone oil [ 72 , 73 ], poly(ethylene glycol) (PEG) [ 74 , 75 ], poly(aspartamide) [ 76 ], and poly(allylamine) [ 77 ]. Thiolation of both hydrophobic and hydrophilic polymers generally increases mucoadhesivity [ 2 ].…”

Section: Reaction Types and Applicationsmentioning

confidence: 99%

Thiol- and Disulfide-Based Stimulus-Responsive Soft Materials and Self-Assembling Systems

Beaupre

Weiss

2021

Molecules

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Entirely S-Protected Thiolated Silicone: A Novel Hydrophobic Mucoadhesive and Skin Adhesive

Cited by 11 publications

References 31 publications

Less Reactive Thiol Ligands: Key towards Highly Mucoadhesive Drug Delivery Systems

Less Reactive Thiol Ligands: Key towards Highly Mucoadhesive Drug Delivery Systems

Thiolated Silicone Oils as New Components of Protective Creams in the Prevention of Skin Diseases

Thiol- and Disulfide-Based Stimulus-Responsive Soft Materials and Self-Assembling Systems

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