Influence of diisocyanate reactivity and water solubility on the formation and the mechanical properties of gelatin-based networks in water

2013 ◽  
Vol 1569 ◽  
pp. 15-20 ◽  
Author(s):  
Tim Gebauer ◽  
Axel T. Neffe ◽  
Andreas Lendlein
Keyword(s):  
Mechanical Properties ◽  
Ethyl Ester ◽  
Water Solubility ◽  
Network Formation ◽  
Gelation Time ◽  
High Water ◽  
Toluene Diisocyanate ◽  
Limiting Factor ◽  
Inhomogeneous Materials ◽  
Solubility In Water

ABSTRACTGelatin can be covalently crosslinked in aqueous solution by application of diisocyanates like L-lysine diisocyanate ethyl ester in order to form hydrogels. Reaction of isocyanate groups with water is however a limiting factor in hydrogel network formation and can strongly influence the outcome of the crosslinking process. Here, diisocyanates with different water solubility and reactivity were applied for the formation of gelatin-based hydrogel networks and the mechanical properties of the hydrogels were investigated to gain a better understanding of starting material/ hydrogel property relations. L-Lysin diisocyanate ethyl ester (LDI), 2,4-toluene diisocyanate (TDI), 1,4-butane diisocyanate (BDI), and isophorone diisocyanate (IPDI) were selected, having different solubility in water ranging from 10-4 to 10-2 mol·L-1. BDI and LDI were estimated to have average reactive isocyanates groups, whereas TDI is highly reactive and IPDI has low reactivity. Formed hydrogels showed different morphologies and were partially very inhomogeneous. Gelation time (1 to 50 minutes), water uptake (300 to 900 wt.-%), and mechanical properties determined by tensile tests (E-moduli 35 to 370 kPa) and rheology (Shear moduli 4.5 to 19.5 kPa) showed that high water solubility as well as high reactivity leads to the formation of poorly crosslinked or inhomogeneous materials. Nevertheless, diisocyanates with lower solubility in water and low reactivity are able to form stable, homogeneous hydrogel networks with gelatin in water.

scholarly journals New Active Pharmaceutical Ingredient-Ionic Liquids (API-ILs) Derived from Indomethacin and Mebendazole

Proceedings ◽  
2018 ◽  
Vol 9 (1) ◽  
pp. 48 ◽  
Author(s):  
◽  
Emilia Tojo
Keyword(s):  
Ionic Liquids ◽  
Water Solubility ◽  
Methanesulfonic Acid ◽  
Active Pharmaceutical Ingredient ◽  
High Water ◽  
Solubility In Water ◽  
Pharmaceutical Ingredients ◽  
Low Toxicity ◽  
Low Solubility ◽  
High Water Solubility

The transformation of two solid Active Pharmaceutical Ingredients (APIs) into new ionic liquids (IL)s that incorporate APIs (API-ILs) is reported. The structures of the APIs (indomethacin and mebendazole) were selected by their susceptibility to being transformed into API-ILs (either to form the cation or the anion) and their limited bioavailability due to their low solubility in water. The counterions, such as those derived from 2-dimethylaminoethanol (DMEA), tetramethylguanidine (TMG), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,4-diazabicyclo[2.2.2] (TED), <i>p</i>-toluensulfonic acid, glycolic acid, methanesulfonic acid, and saccharin, were carefully chosen, aiming for high biocompatibility, low toxicity, and high water solubility. The synthesis was carried out by direct treatment of the API with the corresponding selected acid or base. Finally, the solubility in water of all the synthesized salts was determined.

scholarly journals An Approach to the Use of Glycol Alkoxysilane–Polysaccharide Hybrids in the Conservation of Historical Building Stones

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 938
Author(s):  
Miguel Meléndez-Zamudio ◽  
Ileana Bravo-Flores ◽  
Eulalia Ramírez-Oliva ◽  
Antonio Guerra-Contreras ◽  
Gilberto Álvarez-Guzmán ◽  
...  
Keyword(s):  
Water Solubility ◽  
High Water ◽  
Water Soluble ◽  
Building Stones ◽  
Historical Building ◽  
Solubility In Water ◽  
Angle Measurements ◽  
Historical Monuments ◽  
Contact Angle Measurements ◽  
Stone Consolidants

Stone consolidants have been widely used to protect historical monuments. Consolidants and hydrophobic formulations based on the use of tetraethoxysilane (TEOS) and alkylalkoxysilanes as precursors have been widely applied, despite their lack of solubility in water and requirement to be applied in organic media. In the search for a “greener” alternative based on silicon that has potential use in this field, the use of tetrakis(2-hydroxyethyl)silane (THEOS) and tris(2-hydroxyethyl)methyl silane (MeTHEOS) as precursors, due their high water solubility and stability, is proposed in this paper. It is already known that THEOS and MeTHEOS possess remarkable compatibility with different natural polysaccharides. The investigated approach uses the water-soluble silanes THEOS–chitosan and MeTHEOS–chitosan as a basis for obtaining hybrid consolidants and hydrophobic formulations for the conservation of siliceous and calcareous stones. In the case of calcareous systems, their incompatibility with alkoxysilanes is known and is expected to be solved by the developed hybrid consolidant. Their application in the conservation of building stones from historical and archeological sites from Guanajuato, México was studied. The evaluation of the consolidant and hydrophobic formulation treatment was mainly conducted by determining the mechanical properties and contact angle measurements with satisfactory results in terms of the performance and compatibility with the studied stones.

scholarly journals Formulation and Characterization of an Effervescent Hydrogen-Generating Tablet

2021 ◽  
Vol 14 (12) ◽  
pp. 1327
Author(s):  
Moritz Rosch ◽  
Kurt Lucas ◽  
Jozef Al-Gousous ◽  
Ulrich Pöschl ◽  
Peter Langguth
Keyword(s):  
Mechanical Properties ◽  
Oral Delivery ◽  
Water Solubility ◽  
Hydrogen Generation ◽  
High Water ◽  
Sweet Taste ◽  
Dry Granulation ◽  
Medical Gas ◽  
And Oxidative Stress

Hydrogen, as a medical gas, is a promising emerging treatment for many diseases related to inflammation and oxidative stress. Molecular hydrogen can be generated through hydrogen ion reduction by a metal, and magnesium-containing effervescent tablets constitute an attractive formulation strategy for oral delivery. In this regard, saccharide-based excipients represent an important class of potential fillers with high water solubility and sweet taste. In this study, we investigated the effect of different saccharides on the morphological and mechanical properties and the disintegration of hydrogen-generating effervescent tablets prepared by dry granulation. Mannitol was found to be superior to other investigated saccharides and promoted far more rapid hydrogen generation combined with acceptable mechanical properties. In further product optimization involving investigation of lubricant effects, adipic acid was selected for the optimized tablet, due to regulatory considerations.

Tailoring of Mechanical Properties of Diisocyanate Crosslinked Gelatin-Based Hydrogels

2013 ◽  
Vol 1569 ◽  
pp. 3-8 ◽  
Author(s):  
Axel T. Neffe ◽  
Tim Gebauer ◽  
Andreas Lendlein
Keyword(s):  
Mechanical Properties ◽  
Network Formation ◽  
Polymer Network ◽  
Polymeric Materials ◽  
Toluene Diisocyanate ◽  
Crosslinking Reaction ◽  
Young’S Moduli ◽  
Physical Interactions ◽  
Reaction In Water ◽  
Full Conversion

ABSTRACTPolymer network formation is an important tool for tailoring mechanical properties of polymeric materials. One option to synthesize a network is the addition of bivalent crosslinkers reacting with functional groups present in a polymer. In case of polymer network syntheses based on biopolymers, performing such a crosslinking reaction in water is sometimes necessary in view of the solubility of the biopolymer, such as gelatin, and can be beneficial to avoid potential contamination of the formed material with organic solvents in view of applications in biomedicine. In the case of applying diisocyanates for the crosslinking in water, it is necessary to show that the low molecular weight bifunctional crosslinker has fully reacted, while tailoring of the mechanical properties of the resulting hydrogels is possible despite the complex reaction mechanism. Here, the formation of gelatin-based hydrogel networks with the diisocyanates 2,4-toluene diisocyanate, 1,4-butane diisocyanate, and isophorone diisocyanate is presented. It is shown that extensive washing of materials is required to ensure full conversion of the diisocyanates. The use of different diisocyanates gives hydrogels covering a large range of Young’s moduli (12-450 kPa). The elongations at break (up to 83%) as well as the maximum tensile strengths (up to 410 kPa) of the hydrogels described here are much higher than for lysine diisocyanate ethyl ester crosslinked gelatin reported before. Rheological investigations suggest that the network formation in some cases is due to physical interactions and entanglements rather than covalent crosslink formation.

Are we ready to replace dimercaprol (BAL) as an arsenic antidote?

1997 ◽  
Vol 16 (8) ◽  
pp. 460-465 ◽  
Author(s):  
Harald Mückter ◽  
Bernhard Lieb ◽  
Franz-Xaver Reich ◽  
Göran Hunder ◽  
Udo Walther ◽  
...  
Keyword(s):  
Water Solubility ◽  
Therapeutic Index ◽  
High Water ◽  
Experimental Models ◽  
Limiting Factor ◽  
Arsenic Poisoning ◽  
High Therapeutic Index ◽  
Low Toxicity ◽  
Epithelial Barriers ◽  
Exchange Resins

1 Dimercaprol (BAL), 2,3-dimercaptopropanesulpho nate sodium (DMPS) and meso-2,3-dimercaptosucci nic acid (DMSA) are effective arsenic antidotes, but the question which one is preferable for optimal therapy of arsenic poisoning is still open to discussion. Major drawbacks of BAL include (a) its low therapeutic index, (b) its tendency to redistribute arsenic to brain and testes, for example, (c) the need for (painful) intramuscular injection and (d) its unpleasant odour. 2 The newer antidotes DMPS and DMSA feature low toxicity and high therapeutic index. They can be given orally or intravenously due to their high water solubility. While these advantages make it likely that DMPS and DMSA will replace BAL for the treatment of chronic arsenic poisoning, acute intoxication - espe cially with lipophilic organoarsenicals - may pose a problem for the hydrophilic antidotes, because their ionic nature can adversely affect intracellular avail ability. 3 This article focuses on aspects dealing with the power of BAL, DMPS, and DMSA to mobilize tissue-bound arsenic in various experimental models, such as monolayers of MDCK (=Madin-Darby canine kidney) cells from dog kidney, isolated perfused liver from guinea-pigs, and perfused jejunal segments from rat small intestine. 4 The results show that hydrophilic DMPS and DMSA may fail to rapidly and completely remove arsenic that has escaped from the extracellular space across tight epithelial barriers. However, owing to their low toxicity, which allows larger doses to be applied, and the potential modification of their pharmacokinetics by means of inert oral anion-exchange resins, DMPS and DMSA may advantageously replace BAL when ever intervention time is not critical. With severe intoxication by organic arsenicals, when the point-of- no-return is a limiting factor, BAL may still have a place as an arsenic antidote.

scholarly journals Synthesis of morpholinium salts based on chloroacylated derivatives of dihydroquercetin

2019 ◽  
Vol 59 (7) ◽  
pp. 37-42
Author(s):  
Anton O. Pozdeev ◽  
◽  
Alexander M. Koroteev ◽  
Sofia N. Pimankina ◽  
Mikhail P. Koroteev ◽  
...  
Keyword(s):  
Water Solubility ◽  
Biological Activities ◽  
High Water ◽  
Water Soluble ◽  
Synthetic Approach ◽  
Solubility In Water ◽  
Natural Amino Acids ◽  
Synthetic Approaches ◽  
Derivatives Of ◽  
Low Solubility

The flavonoid dihydroquercetin and its esterified derivatives possess various biological activities and are widely used as dietary supplements and in pharmacology. A significant disadvantage of this flavonoid is its low solubility in water at ordinary temperatures of up to 0.03%, which negatively affects its biological activity. Nature overcomes this problem by glycosylation, sulfation, and phosphorylation. In chemistry and pharmacology to overcome this problem, there are several synthetic approaches. For dihydroquercetin (DHQ) is the inclusion of DHQ in the cyclodextrin matrix or the formation of a complex of DHQ with basic natural amino acids. In this paper, a method is proposed for obtaining water-soluble morpholinium salts based on chloroacylated derivatives of DHQ. The acylation reaction was carried out in dioxane, pyridine was used as an acceptor of choric hydrogen. The target compounds were obtained with a yield of 68-79%. As a result, chlorinated derivatives based on DHQ and its acyl and benzyl derivatives were synthesized. These derivatives in the interaction with morpholine form its salts, which, as it turned out, have a high water solubility. Pentamorpholine salt of DHQ had the highest solubility in water, up to 6.5% at room temperature, which is 200 times more soluble than the original DHQ. The proposed synthetic approach to increase the water solubility of acyl derivatives of DHQ can be extended using other nitrogenous bases and other haloacyl derivatives of DHQ.

Hydrogels as Antibacterial Biomaterials

2018 ◽  
Vol 24 (8) ◽  
pp. 843-854 ◽  
Author(s):  
Weiguo Xu ◽  
Shujun Dong ◽  
Yuping Han ◽  
Shuqiang Li ◽  
Yang Liu
Keyword(s):  
Mechanical Properties ◽  
Drug Delivery ◽  
Tissue Engineering ◽  
Water Content ◽  
Oxygen Permeability ◽  
Structural Diversity ◽  
High Water ◽  
Clinical Applications ◽  
High Water Content ◽  
Biomedical Field

Hydrogels, as a class of materials for tissue engineering and drug delivery, have high water content and solid-like mechanical properties. Currently, hydrogels with an antibacterial function are a research hotspot in biomedical field. Many advanced antibacterial hydrogels have been developed, each possessing unique qualities, namely high water swellability, high oxygen permeability, improved biocompatibility, ease of loading and releasing drugs and structural diversity. In this article, an overview is provided on the preparation and applications of various antibacterial hydrogels. Furthermore, the prospects in biomedical researches and clinical applications are predicted.

scholarly journals Anti-Inflammatory Properties of Injectable Betamethasone-Loaded Tyramine-Modified Gellan Gum/Silk Fibroin Hydrogels

Biomolecules ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1456
Author(s):  
Isabel Matos Oliveira ◽  
Cristiana Gonçalves ◽  
Myeong Eun Shin ◽  
Sumi Lee ◽  
Rui Luis Reis ◽  
...  
Keyword(s):  
Rheumatoid Arthritis ◽  
Mechanical Properties ◽  
Silk Fibroin ◽  
Therapeutic Efficacy ◽  
Composite Structures ◽  
Gelation Time ◽  
Polymeric Materials ◽  
Gellan Gum ◽  
Traditional Use

Rheumatoid arthritis is a rheumatic disease for which a healing treatment does not presently exist. Silk fibroin has been extensively studied for use in drug delivery systems due to its uniqueness, versatility and strong clinical track record in medicine. However, in general, natural polymeric materials are not mechanically stable enough, and have high rates of biodegradation. Thus, synthetic materials such as gellan gum can be used to produce composite structures with biological signals to promote tissue-specific interactions while providing the desired mechanical properties. In this work, we aimed to produce hydrogels of tyramine-modified gellan gum with silk fibroin (Ty–GG/SF) via horseradish peroxidase (HRP), with encapsulated betamethasone, to improve the biocompatibility and mechanical properties, and further increase therapeutic efficacy to treat rheumatoid arthritis (RA). The Ty–GG/SF hydrogels presented a β-sheet secondary structure, with gelation time around 2–5 min, good resistance to enzymatic degradation, a suitable injectability profile, viscoelastic capacity with a significant solid component and a betamethasone-controlled release profile over time. In vitro studies showed that Ty–GG/SF hydrogels did not produce a deleterious effect on cellular metabolic activity, morphology or proliferation. Furthermore, Ty–GG/SF hydrogels with encapsulated betamethasone revealed greater therapeutic efficacy than the drug applied alone. Therefore, this strategy can provide an improvement in therapeutic efficacy when compared to the traditional use of drugs for the treatment of rheumatoid arthritis.

scholarly journals Generation of Photopolymerized Microparticles Based on PEGDA Using Microfluidic Devices. Part 1. Initial Gelation Time and Mechanical Properties of the Material

Micromachines ◽  
2021 ◽  
Vol 12 (3) ◽  
pp. 293
Author(s):  
José M. Acosta-Cuevas ◽  
José González-García ◽  
Mario García-Ramírez ◽  
Víctor H. Pérez-Luna ◽  
Erick Omar Cisneros-López ◽  
...  
Keyword(s):  
Mechanical Properties ◽  
Gelation Time ◽  
Mesh Size ◽  
Microfluidic Devices ◽  
Future Generation ◽  
Mechanical Tests ◽  
Continuous Systems ◽  
Polyethylene Glycol Diacrylate ◽  
Glycol Diacrylate ◽  
Close Relationship

Photopolymerized microparticles are made of biocompatible hydrogels like Polyethylene Glycol Diacrylate (PEGDA) by using microfluidic devices are a good option for encapsulation, transport and retention of biological or toxic agents. Due to the different applications of these microparticles, it is important to investigate the formulation and the mechanical properties of the material of which they are made of. Therefore, in the present study, mechanical tests were carried out to determine the swelling, drying, soluble fraction, compression, cross-linking density (Mc) and mesh size (ξ) properties of different hydrogel formulations. Tests provided sufficient data to select the best formulation for the future generation of microparticles using microfluidic devices. The initial gelation times of the hydrogels formulations were estimated for their use in the photopolymerization process inside a microfluidic device. Obtained results showed a close relationship between the amount of PEGDA used in the hydrogel and its mechanical properties as well as its initial gelation time. Consequently, it is of considerable importance to know the mechanical properties of the hydrogels made in this research for their proper manipulation and application. On the other hand, the initial gelation time is crucial in photopolymerizable hydrogels and their use in continuous systems such as microfluidic devices.

Sign in / Sign up

Export Citation Format

Share Document