Synthesis and hydrolytic degradation of a random copolymer derived from 1,4-dioxan-2-one and glycolide

2004 ◽  
Vol 42 (13) ◽  
pp. 2558-2566 ◽  
Author(s):  
Narayan Bhattarai ◽  
Wen Ying Jiang ◽  
Hak Yong Kim ◽  
Douck Rae Lee ◽  
Soo Jin Park
Keyword(s):  
Hydrolytic Degradation ◽  
Random Copolymer

Development of HPLC Method for the Purity Test by Design of Experiments and Determination of Activation Energy of Hydrolytic Degradation Reactions of Sofosbuvir

2020 ◽  
Vol 16 (7) ◽  
pp. 976-987
Author(s):  
Jakub Petřík ◽  
Jakub Heřt ◽  
Pavel Řezanka ◽  
Filip Vymyslický ◽  
Michal Douša
Keyword(s):  
Activation Energy ◽  
Design Of Experiments ◽  
Mobile Phase ◽  
Hydrolytic Degradation ◽  
Isoconversional Method ◽  
Hplc Method ◽  
Organic Modifier ◽  
Calculation Methods ◽  
Degradation Reactions

Background: The present study was focused on the development of HPLC method for purity testing of sofosbuvir by the Design of Experiments and determination of the activation energy of hydrolytic degradation reactions of sofosbuvir using HPLC based on the kinetics of sofosbuvir degradation. Methods: Following four factors for the Design of Experiments were selected, stationary phase, an organic modifier of the mobile phase, column temperature and pH of the mobile phase. These factors were examined in two or three level experimental design using Modde 11.0 (Umetrics) software. The chromatographic parameters like resolution, USP tailing and discrimination factor were calculated and analysed by partial least squares. The chromatography was performed based on Design of Experiments results with the mobile phase containing ammonium phosphate buffer pH 2.5 and methanol as an organic modifier. Separation was achieved using gradient elution on XBridge BEH C8 at 50 °C and a flow rate of 0.8 mL/min. UV detection was performed at 220 nm. The activation energy of hydrolytic degradation reactions of sofosbuvir was evaluated using two different calculation methods. The first method is based on the slope of dependence of natural logarithm of the rate constant on inverted thermodynamic temperature and the second approach is the isoconversional method. Results and Conclusion: Calculated activation energies were 77.9 ± 1.1 kJ/mol for the first method and 79.5 ± 3.2 kJ/mol for the isoconversional method. The results can be considered to be identical, therefore both calculation methods are suitable for the determination of the activation energy of degradation reactions.

scholarly journals Quadruple Hydrogen Bond-Containing A-AB-A Triblock Copolymers: Probing the Influence of Hydrogen Bonding in the Central Block

Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4705
Author(s):  
Boer Liu ◽  
Xi Chen ◽  
Glenn A. Spiering ◽  
Robert B. Moore ◽  
Timothy E. Long
Keyword(s):  
Hydrogen Bonding ◽  
Self Assembly ◽  
Microphase Separation ◽  
Triblock Copolymers ◽  
Random Copolymer ◽  
Thermomechanical Properties ◽  
Structure Property ◽  
Scanning Calorimetry ◽  
Central Block ◽  
Quadruple Hydrogen Bonding

This work reveals the influence of pendant hydrogen bonding strength and distribution on self-assembly and the resulting thermomechanical properties of A-AB-A triblock copolymers. Reversible addition-fragmentation chain transfer polymerization afforded a library of A-AB-A acrylic triblock copolymers, wherein the A unit contained cytosine acrylate (CyA) or post-functionalized ureido cytosine acrylate (UCyA) and the B unit consisted of n-butyl acrylate (nBA). Differential scanning calorimetry revealed two glass transition temperatures, suggesting microphase-separation in the A-AB-A triblock copolymers. Thermomechanical and morphological analysis revealed the effects of hydrogen bonding distribution and strength on the self-assembly and microphase-separated morphology. Dynamic mechanical analysis showed multiple tan delta (δ) transitions that correlated to chain relaxation and hydrogen bonding dissociation, further confirming the microphase-separated structure. In addition, UCyA triblock copolymers possessed an extended modulus plateau versus temperature compared to the CyA analogs due to the stronger association of quadruple hydrogen bonding. CyA triblock copolymers exhibited a cylindrical microphase-separated morphology according to small-angle X-ray scattering. In contrast, UCyA triblock copolymers lacked long-range ordering due to hydrogen bonding induced phase mixing. The incorporation of UCyA into the soft central block resulted in improved tensile strength, extensibility, and toughness compared to the AB random copolymer and A-B-A triblock copolymer comparisons. This study provides insight into the structure-property relationships of A-AB-A supramolecular triblock copolymers that result from tunable association strengths.

scholarly journals Synthesis, Characterization and Bactericidal Activity of a 4-Ammoniumbuthylstyrene-Based Random Copolymer

Polymers ◽  
2021 ◽  
Vol 13 (7) ◽  
pp. 1140
Author(s):  
Silvana Alfei ◽  
Gabriella Piatti ◽  
Debora Caviglia ◽  
Anna Maria Schito
Keyword(s):  
Antibacterial Activity ◽  
Bactericidal Activity ◽  
Antimicrobial Agents ◽  
Water Solubility ◽  
Physicochemical Characterization ◽  
Random Copolymer ◽  
Water Soluble ◽  
Cationic Polymers ◽  
Severe Infections

The growing resistance of bacteria to current chemotherapy is a global concern that urgently requires new and effective antimicrobial agents, aimed at curing untreatable infection, reducing unacceptable healthcare costs and human mortality. Cationic polymers, that mimic antimicrobial cationic peptides, represent promising broad-spectrum agents, being less susceptible to develop resistance than low molecular weight antibiotics. We, thus, designed, and herein report, the synthesis and physicochemical characterization of a water-soluble cationic copolymer (P5), obtained by copolymerizing the laboratory-made monomer 4-ammoniumbuthylstyrene hydrochloride with di-methyl-acrylamide as uncharged diluent. The antibacterial activity of P5 was assessed against several multi-drug-resistant clinical isolates of both Gram-positive and Gram-negative species. Except for strains characterized by modifications of the membrane charge, most of the tested isolates were sensible to the new molecule. P5 showed remarkable antibacterial activity against several isolates of genera Enterococcus, Staphylococcus, Pseudomonas, Klebsiella, and against Escherichia coli, Acinetobacter baumannii and Stenotrophomonas maltophilia, displaying a minimum MIC value of 3.15 µM. In time-killing and turbidimetric studies, P5 displayed a rapid non-lytic bactericidal activity. Due to its water-solubility and wide bactericidal spectrum, P5 could represent a promising novel agent capable of overcoming severe infections sustained by bacteria resistant the presently available antibiotics.

Synthesis and Properties of Biodegradable Liquid Crystalline Poly(ester-Urethane)s Based on Poly(L-Lactic Acid)

2013 ◽  
Vol 652-654 ◽  
pp. 459-462
Author(s):  
Ya Tong Guo ◽  
Zhu Zheng ◽  
Zhen Qi Hou ◽  
Jie Du
Keyword(s):  
Phase Transition ◽  
Thermal Stability ◽  
Lactic Acid ◽  
Physical Properties ◽  
Liquid Crystalline ◽  
Degradation Rate ◽  
Hydrolytic Degradation ◽  
Hexamethylene Diisocyanate ◽  
Solution Polymerization ◽  
Phase Transition Temperatures

A series of biodegradable segmented liquid crystalline poly(ester-urethane)s were prepared by solution polymerization of poly(L-lactic acid) (PLLA), mesogenic diol prepolymer poly(butylene terephthaloyldioxy dibenzoates) (MD), and hexamethylene diisocyanate (HDI). The MD content was varied from 0 to 40 mol% so that the effects of the mesogen content on the thermal and physical properties, and hydrolytic degradation were examined respectively. It was found that introducing mesogens units could increase the thermal stability and the elastic properties, while reduced the phase transition temperatures and the hydrolytic degradation rate.

scholarly journals Highly absorbent hydrogels comprised from interpenetrated networks of alginate–polyurethane for biomedical applications

2021 ◽  
Vol 32 (6) ◽  
Author(s):  
Jesús A. Claudio-Rizo ◽  
Nallely Escobedo-Estrada ◽  
Sara L. Carrillo-Cortes ◽  
Denis A. Cabrera-Munguía ◽  
Tirso E. Flores-Guía ◽  
...  
Keyword(s):  
Biomedical Applications ◽  
Degradation Rate ◽  
High Capacity ◽  
Hydrolytic Degradation ◽  
Absorption Capacity ◽  
Amide Bonds ◽  
E Coli ◽  
Swelling Capacity ◽  
And Storage ◽  
Potential Area

AbstractDeveloping new approaches to improve the swelling, degradation rate, and mechanical properties of alginate hydrogels without compromising their biocompatibility for biomedical applications represents a potential area of research. In this work, the generation of interpenetrated networks (IPN) comprised from alginate–polyurethane in an aqueous medium is proposed to design hydrogels with tailored properties for biomedical applications. Aqueous polyurethane (PU) dispersions can crosslink and interpenetrate alginate chains, forming amide bonds that allow the structure and water absorption capacity of these novel hydrogels to be regulated. In this sense, this work focuses on studying the relation of the PU concentration on the properties of these hydrogels. The results indicate that the crosslinking of the alginate with PU generates IPN hydrogels with a crystalline structure characterized by a homogeneous smooth surface with high capacity to absorb water, tailoring the degradation rate, thermal decomposition, and storage module, not altering the native biocompatibility of alginate, providing character to inhibit the growth of E. coli and increasing also its hemocompatibility. The IPN hydrogels that include 20 wt.% of PU exhibit a reticulation index of 46 ± 4%, swelling capacity of 545 ± 13% at 7 days of incubation at physiological pH, resistance to both acidic and neutral hydrolytic degradation, mechanical improvement of 91 ± 1%, and no cytotoxicity for monocytes and fibroblasts growing for up to 72 h of incubation. These results indicate that these novel hydrogels can be used for successful biomedical applications in the design of wound healing dressings.

scholarly journals Effect of Moisture Content on the Processing and Mechanical Properties of a Biodegradable Polyester

Polymers ◽  
2021 ◽  
Vol 13 (10) ◽  
pp. 1616
Author(s):  
Vincenzo Titone ◽  
Antonio Correnti ◽  
Francesco Paolo La Mantia
Keyword(s):  
Mechanical Properties ◽  
Tensile Strength ◽  
Moisture Content ◽  
Mechanical Testing ◽  
Hydrolytic Degradation ◽  
Slight Reduction ◽  
Biodegradable Polyester ◽  
Molding Process ◽  
Elongation At Break ◽  
Effect Of Moisture

This work is focused on the influence of moisture content on the processing and mechanical properties of a biodegradable polyester used for applications in injection molding. The pellets of the biodegradable polyester were exposed under different relative humidity conditions at a constant temperature before being compression molded. The compression-molded specimens were again placed under the above conditions before the mechanical testing. With all these samples, it is possible to determine the effect of moisture content on the processing and mechanical properties separately, as well as the combined effect of moisture content on the mechanical properties. The results obtained showed that the amount of absorbed water—both before processing and before mechanical testing—causes an increase in elongation at break and a slight reduction of the elastic modulus and tensile strength. These changes have been associated with possible hydrolytic degradation during the compression molding process and, in particular, with the plasticizing action of the moisture absorbed by the specimens.

scholarly journals Comprehensive Hydrolytic Degradation Study of a New Poly(ester-amide) Used for Total Meniscus Replacement

2021 ◽  
pp. 109617
Author(s):  
Catherine E. Miles ◽  
Mariana R.N. Lima ◽  
Fatima Buevich ◽  
Christine Gwin ◽  
N.Sanjeeva Murthy ◽  
...  
Keyword(s):  
Hydrolytic Degradation ◽  
Degradation Study ◽  
Meniscus Replacement

scholarly journals Self-Crosslinked Ellipsoidal Poly(Tannic Acid) Particles for Bio-Medical Applications

Molecules ◽  
2021 ◽  
Vol 26 (9) ◽  
pp. 2429
Author(s):  
Nurettin Sahiner
Keyword(s):  
Tannic Acid ◽  
Hydrolytic Degradation ◽  
Single Step ◽  
Trolox Equivalent Antioxidant Capacity ◽  
Total Phenol Content ◽  
Frap Assay ◽  
E Coli ◽  
Gram Positive Bacteria ◽  
Trolox Equivalent ◽  
Free Media

Self-crosslinking of Tannic acid (TA) was accomplished to obtain poly(tannic acid) (p(TA)) particles in single step, surfactant free media using sodium periodate (NaIO4) as an oxidizing agent. Almost monodisperse p(TA) particles with 981 ± 76 nm sizes and −22 ± 4 mV zeta potential value with ellipsoidal shape was obtained. Only slight degradation of p(TA) particles with 6.8 ± 0.2% was observed at pH 7.4 in PBS up to 15 days because of the irreversible covalent formation between TA units, suggesting that hydrolytic degradation is independent from the used amounts of oxidation agents. p(TA) particles were found to be non-hemolytic up to 0.5 mg/mL concentration and found not to affect blood clotting mechanism up to 2 mg/mL concentration. Antioxidant activity of p(TA) particles was investigated by total phenol content (TPC), ferric reducing antioxidant potential (FRAP), trolox equivalent antioxidant capacity (TEAC), total flavanoid content (TFC), and Fe (II) chelating activity. p(TA) particles showed strong antioxidant capability in comparison to TA molecules, except FRAP assay. The antibacterial activity of p(TA) particles was investigated by micro-dilution technique on E. coli as Gram‑negative and S. aureus as Gram-positive bacteria and found that p(TA) particles are more effective on S. aureus with over 50% inhibition at 20 mg/mL concentration attained.

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