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Keywords = aminolyzation

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19 pages, 10032 KiB  
Article
Synthesis, Characterization, and Enzyme Conjugation of Polycaprolactone Nanofibers for Tissue Engineering
by Chandana B. Shivakumar, Nithya Rani Raju, Pruthvi G. Ramu, Prashant M. Vishwanath, Ekaterina Silina, Victor Stupin and Raghu Ram Achar
Pharmaceutics 2025, 17(8), 953; https://doi.org/10.3390/pharmaceutics17080953 - 23 Jul 2025
Viewed by 400
Abstract
Background/Objectives: A nanostructured membrane of polycaprolactone (a synthetic polymer) was synthesized using an electrospinning technique aiming to enhance its hydrophilicity and rate of degradation by surface modification via aminolysis. Since polycaprolactone nanofibrous films are naturally hydrophobic and with slow degradation, which restricts [...] Read more.
Background/Objectives: A nanostructured membrane of polycaprolactone (a synthetic polymer) was synthesized using an electrospinning technique aiming to enhance its hydrophilicity and rate of degradation by surface modification via aminolysis. Since polycaprolactone nanofibrous films are naturally hydrophobic and with slow degradation, which restricts their use in biological systems, amino groups were added to the fiber surface using the aminolysis technique, greatly increasing the wettability of the membranes. Methods: Polycaprolactone nanofibrous membranes were synthesized via the electrospinning technique and surface modification by aminolysis. Trypsin, pepsin, and pancreatin were conjugated onto the aminolyzed PNF surface to further strengthen biocompatibility by enhancing the hydrophilicity, porosity, and biodegradation rate. SEM, FTIR, EDX, and liquid displacement method were performed to investigate proteolytic efficiency and morphological and physical characteristics such as hydrophilicity, porosity, and degradation rates. Results: Enzyme activity tests, which showed a zone of clearance, validated the successful enzyme conjugation and stability over a wide range of pH and temperatures. Scanning electron microscopy (SEM) confirms the smooth morphology of nanofibers with diameters ranging from 150 to 950 nm. Fourier transform infrared spectroscopy (FTIR) revealed the presence of O–H, C–O, C=O, C–N, C–H, and O–H functional groups. Energy-dispersive X-ray (EDX) elemental analysis indicates the presence of carbon, oxygen, and nitrogen atoms owing to the presence of peptide and amide bonds. The liquid displacement technique and contact angle proved that Pepsin-PNFs possess notably increased porosity (88.50% ± 0.31%) and hydrophilicity (57.6° ± 2.3 (L), 57.9° ± 2.5 (R)), respectively. Pancreatin-PNFs demonstrated enhanced enzyme activity and degradation rate on day 28 (34.61%). Conclusions: These enzyme-conjugated PNFs thus show improvements in physicochemical properties, making them ideal candidates for various biomedical applications. Future studies must aim for optimization of enzyme conjugation and in vitro and in vivo performance to investigate the versatility of these scaffolds. Full article
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12 pages, 2884 KiB  
Article
The Production and Characterization of an Aminolyzed Polyhydroxyalkanoate Membrane and Its Cytocompatibility with Osteoblasts
by Qiulan Luo, Fuming Zou, Dongjuan Yang, Yongping Huang, Dajie Xian, Ying Nie, Zhenxia Zhang, Yuzhong Zheng, Yaqun Liu, Fei Zhou, Peikui Yang, Yuting Jiang, Xianjing Huang and Xianghui Zou
Molecules 2025, 30(4), 950; https://doi.org/10.3390/molecules30040950 - 18 Feb 2025
Viewed by 551
Abstract
Polyhydroxyalkanoates (PHAs), recognized as a medical biomaterial, have been proven to promote cell proliferation and tissue repair. PHA has a variety of forms: PHB, PHV, PHHx, and PHBHHx, etc. In this study, PHBHHx was selected as the precursor to fabricate biopolyester films. Specifically, [...] Read more.
Polyhydroxyalkanoates (PHAs), recognized as a medical biomaterial, have been proven to promote cell proliferation and tissue repair. PHA has a variety of forms: PHB, PHV, PHHx, and PHBHHx, etc. In this study, PHBHHx was selected as the precursor to fabricate biopolyester films. Specifically, a novel type of biopolyester film was generated through an ammonolysis cross-linking reaction in conjunction with polyamidoamine dendrimer G2.0 (PAMAM). The properties of the resultant biopolyester films were comprehensively evaluated, encompassing surface characteristics, amino group content, and water contact angle. The drug-loading properties and compatibility with osteoblasts of the biopolyester films were also determined. The findings revealed that following aminolysis, the biopolyester film surface exhibited enhanced roughness and an enlarged surface area. Moreover, as the aminolysis duration extended, the hydrophilicity and drug-loading efficiency were significantly augmented. Post-aminolysis, the PHBHHx membrane exhibited a more favorable environment for the adhesion and proliferation of osteoblasts. Overall, the biopolyester film developed in this study provides novel insights and materials for tissue engineering, especially bone tissue repair. Full article
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15 pages, 4394 KiB  
Article
Surface Heparinization of a Magnesium-Based Alloy: A Comparison Study of Aminopropyltriethoxysilane (APTES) and Polyamidoamine (PAMAM) Dendrimers
by Masoumeh Ebrahimi, Atefeh Solouk, Ali Davoodi, Somaye Akbari, Masoumeh Haghbin Nazarpak and Alireza Nouri
J. Funct. Biomater. 2022, 13(4), 296; https://doi.org/10.3390/jfb13040296 - 13 Dec 2022
Cited by 2 | Viewed by 1870
Abstract
Magnesium (Mg)-based alloys are biodegradable metallic biomaterials that show promise in minimizing the risks of permanent metallic implants. However, their clinical applications are restricted due to their rapid in vivo degradation and low surface hemocompatibilities. Surface modifications are critically important for controlling the [...] Read more.
Magnesium (Mg)-based alloys are biodegradable metallic biomaterials that show promise in minimizing the risks of permanent metallic implants. However, their clinical applications are restricted due to their rapid in vivo degradation and low surface hemocompatibilities. Surface modifications are critically important for controlling the corrosion rates of Mg-based alloys and improving their hemocompatibilities. In the present study, two heparinization methods were developed to simultaneously increase the corrosion resistance and hemocompatibility of the AZ31 Mg alloy. In the first method, the surface of the AZ31 alloy was modified by alkali–heat treatment and then aminolyzed by 3-amino propyltriethoxy silane (APTES), a self-assembly molecule, and heparin was grafted onto the aminolyzed surface. In the second method, before heparinization, polyamidoamine dendrimers (PAMAM4-4) were grafted onto the aminolyzed surface with APTES to increase the number of surface functional groups, and heparinization was subsequently performed. The presence of a peak with a wavelength of about 1560 cm−1 in the FTIR spectrum for the sample modified with APTES and dendrimers indicated aminolysis of the surface. The results indicated that the corrosion resistance of the Mg alloy was significantly improved as a result of the formation of a passive layer following the alkali–heat treatment. The results obtained from a potentiodynamic polarization (PDP) test showed that the corrosion current in the uncoated sample decreased from 25 µA to 3.7 µA in the alkali–heat-treated sample. The corrosion current density was reduced by 14 and 50 times in samples treated with the self-assembly molecules, APTES and dendrimers, respectively. After heparinization, the clotting time for pristine Mg was greatly improved. Clotting time increased from 480 s for the pristine Mg sample to 630 s for the APTES- and heparin-modified samples and to 715 s for the PAMAM- and heparin-modified samples. Cell culture data showed a slight improvement in the cell-supporting behavior of the modified samples. Full article
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21 pages, 5383 KiB  
Article
Immobilization of Gelatin on Fibers for Tissue Engineering Applications: A Comparative Study of Three Aliphatic Polyesters
by Oliwia Jeznach, Dorota Kołbuk, Tobias Reich and Paweł Sajkiewicz
Polymers 2022, 14(19), 4154; https://doi.org/10.3390/polym14194154 - 4 Oct 2022
Cited by 8 | Viewed by 2677
Abstract
Immobilization of cell adhesive proteins on the scaffold surface has become a widely reported method that can improve the interaction between scaffold and cells. In this study, three nanofibrous scaffolds obtained by electrospinning of poly(caprolactone) (PCL), poly(L-lactide-co-caprolactone) (PLCL) 70:30, or poly(L-lactide) (PLLA) were [...] Read more.
Immobilization of cell adhesive proteins on the scaffold surface has become a widely reported method that can improve the interaction between scaffold and cells. In this study, three nanofibrous scaffolds obtained by electrospinning of poly(caprolactone) (PCL), poly(L-lactide-co-caprolactone) (PLCL) 70:30, or poly(L-lactide) (PLLA) were subjected to chemical immobilization of gelatin based on aminolysis and glutaraldehyde cross-linking, as well as physisorption of gelatin. Two sets of aminolysis conditions were applied to evaluate the impact of amine group content. Based on the results of the colorimetric bicinchoninic acid (BCA) assay, it was shown that the concentration of gelatin on the surface is higher for the chemical modification and increases with the concentration of free NH2 groups. XPS (X-ray photoelectron spectroscopy) analysis confirmed this outcome. On the basis of XPS results, the thickness of the gelatin layer was estimated to be less than 10 nm. Initially, hydrophobic scaffolds are completely wettable after coating with gelatin, and the time of waterdrop absorption was correlated with the surface concentration of gelatin. In the case of all physically and mildly chemically modified samples, the decrease in stress and strain at break was relatively low, contrary to strongly aminolyzed PLCL and PLLA samples. Incubation testing performed on the PCL samples showed that a chemically immobilized gelatin layer is more stable than a physisorbed one; however, even after 90 days, more than 60% of the initial gelatin concentration was still present on the surface of physically modified samples. Mouse fibroblast L929 cell culture on modified samples indicates a positive effect of both physical and chemical modification on cell morphology. In the case of PCL and PLCL, the best morphology, characterized by stretched filopodia, was observed after stronger chemical modification, while for PLLA, there was no significant difference between modified samples. Results of metabolic activity indicate the better effect of chemical immobilization than of physisorption of gelatin. Full article
(This article belongs to the Special Issue Advanced Polymeric Biomaterials for Tissue Engineering II)
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17 pages, 5835 KiB  
Article
New Imidazolium Ionic Liquids from Recycled Polyethylene Terephthalate Waste for Curing Epoxy Resins as Organic Coatings of Steel
by Ayman M. Atta, Hamad A. Al-Lohedan, Abdelrahman O. Ezzat and Nourah I. Sabeela
Coatings 2020, 10(11), 1139; https://doi.org/10.3390/coatings10111139 - 23 Nov 2020
Cited by 11 | Viewed by 3073
Abstract
Imidazolium ionic liquid (IIL) was prepared from aminolysis of polyethylene terephthalate (PET) waste with pentaethylenehexamine (PEHA) to apply as hardener of epoxy resin. Its purified chemical structures, thermal stability, and thermal characteristics were identified as well as amino phthalamide aminolyzed products. The thermal, [...] Read more.
Imidazolium ionic liquid (IIL) was prepared from aminolysis of polyethylene terephthalate (PET) waste with pentaethylenehexamine (PEHA) to apply as hardener of epoxy resin. Its purified chemical structures, thermal stability, and thermal characteristics were identified as well as amino phthalamide aminolyzed products. The thermal, thermomechanical, and mechanical properties of the cured epoxy resins with different weight percentages of IIL were investigated to optimize the best weight ratio to obtain homogeneous networks. The adhesion, durability, and corrosion resistance of the cured epoxy resins on the steel surfaces were tested to confirm that the best weight ratio of epoxy: IL was 2:1. This ratio achieved higher adhesion strength and salt spray resistance to seawater extended to 1500 h. Full article
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11 pages, 3915 KiB  
Article
Cationic Nanocylinders Promote Angiogenic Activities of Endothelial Cells
by Jung Bok Lee, Daniel A. Balikov, Jae Won Yang, Ki Seok Kim, Hun Kuk Park, Jeong Koo Kim, Il Keun Kwon, Leon M. Bellan and Hak-Joon Sung
Polymers 2016, 8(1), 15; https://doi.org/10.3390/polym8010015 - 14 Jan 2016
Cited by 51 | Viewed by 6982
Abstract
Polymers have been used extensively taking forms as scaffolds, patterned surface and nanoparticle for regenerative medicine applications. Angiogenesis is an essential process for successful tissue regeneration, and endothelial cell–cell interaction plays a pivotal role in regulating their tight junction formation, a hallmark of [...] Read more.
Polymers have been used extensively taking forms as scaffolds, patterned surface and nanoparticle for regenerative medicine applications. Angiogenesis is an essential process for successful tissue regeneration, and endothelial cell–cell interaction plays a pivotal role in regulating their tight junction formation, a hallmark of angiogenesis. Though continuous progress has been made, strategies to promote angiogenesis still rely on small molecule delivery or nuanced scaffold fabrication. As such, the recent paradigm shift from top-down to bottom-up approaches in tissue engineering necessitates development of polymer-based modular engineering tools to control angiogenesis. Here, we developed cationic nanocylinders (NCs) as inducers of cell–cell interaction and investigated their effect on angiogenic activities of human umbilical vein endothelial cells (HUVECs) in vitro. Electrospun poly (l-lactic acid) (PLLA) fibers were aminolyzed to generate positively charged NCs. The aninolyzation time was changed to produce two different aspect ratios of NCs. When HUVECs were treated with NCs, the electrostatic interaction of cationic NCs with negatively charged plasma membranes promoted migration, permeability and tubulogenesis of HUVECs compared to no treatment. This effect was more profound when the higher aspect ratio NC was used. The results indicate these NCs can be used as a new tool for the bottom-up approach to promote angiogenesis. Full article
(This article belongs to the Special Issue Polymers Applied in Tissue Engineering)
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14 pages, 218 KiB  
Article
Synthesis and Antimicrobial Activity of Some New Pyrimidinone and Oxazinone Derivatives Fused with Thiophene Rings Using 2-Chloro-6-ethoxy-4-acetylpyridine as Starting Material
by Aisha S. M. Hossan, Hanaa M. A. Abu-Melha, Mohamed A. Al-Omar and Abd El-Galil E. Amr
Molecules 2012, 17(11), 13642-13655; https://doi.org/10.3390/molecules171113642 - 19 Nov 2012
Cited by 54 | Viewed by 7252
Abstract
A series of pyridines, pyrimidinones, oxazinones and their derivatives were synthesized as antimicrobial agents using citrazinic acid (2,6-dihydroxyisonicotinic acid) as a starting material. α,β-Unsaturated ketones 3ac were condensed with cyanothio-acetamide in the presence of ammonium acetate to give 2-cyanopyridinethiones 4a [...] Read more.
A series of pyridines, pyrimidinones, oxazinones and their derivatives were synthesized as antimicrobial agents using citrazinic acid (2,6-dihydroxyisonicotinic acid) as a starting material. α,β-Unsaturated ketones 3ac were condensed with cyanothio-acetamide in the presence of ammonium acetate to give 2-cyanopyridinethiones 4ac, which were reacted with ethyl chloroacetate to yield the corresponding cyano esters 5ac. The esters 5ac were cyclized by action of sodium methoxide to aminoesters 6ac, which were aminolyzed with ammonia to corresponding aminoamide derivatives 7a-c. Also, the esters 6ac were hydrolyzed with NaOH to the corresponding sodium salt 8ac, which were treated with acetic anhydride to afford 2-methyloxazinones 9ac. The latter compounds were treated with ammonium acetate to afford 2-methylpyrimidinones 10ac, followed by methylation with methyl iodide to yield 2,3-dimethyl-pyrimidinones 11ac. The antimicrobial screening showed that many of these compounds have good antibacterial and antifungal activities comparable to streptomycin and fusidic acid used as reference drugs. Full article
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