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Keywords = difluoroethylation

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16 pages, 7741 KB  
Article
Digital Light Processing of 19F MRI-Traceable Gelatin-Based Biomaterial Inks towards Bone Tissue Regeneration
by Anna Szabó, Kristyna Kolouchova, Laurens Parmentier, Vit Herynek, Ondrej Groborz and Sandra Van Vlierberghe
Materials 2024, 17(12), 2996; https://doi.org/10.3390/ma17122996 - 19 Jun 2024
Cited by 1 | Viewed by 2223
Abstract
Gelatin-based photo-crosslinkable hydrogels are promising scaffold materials to serve regenerative medicine. They are widely applicable in additive manufacturing, which allows for the production of various scaffold microarchitectures in line with the anatomical requirements of the organ to be replaced or tissue defect to [...] Read more.
Gelatin-based photo-crosslinkable hydrogels are promising scaffold materials to serve regenerative medicine. They are widely applicable in additive manufacturing, which allows for the production of various scaffold microarchitectures in line with the anatomical requirements of the organ to be replaced or tissue defect to be treated. Upon their in vivo utilization, the main bottleneck is to monitor cell colonization along with their degradation (rate). In order to enable non-invasive visualization, labeling with MRI-active components like N-(2,2-difluoroethyl)acrylamide (DFEA) provides a promising approach. Herein, we report on the development of a gelatin-methacryloyl-aminoethyl-methacrylate-based biomaterial ink in combination with DFEA, applicable in digital light processing-based additive manufacturing towards bone tissue regeneration. The fabricated hydrogel constructs show excellent shape fidelity in line with the printing resolution, as DFEA acts as a small molecular crosslinker in the system. The constructs exhibit high stiffness (E = 36.9 ± 4.1 kPa, evaluated via oscillatory rheology), suitable to serve bone regeneration and excellent MRI visualization capacity. Moreover, in combination with adipose tissue-derived stem cells (ASCs), the 3D-printed constructs show biocompatibility, and upon 4 weeks of culture, the ASCs express the osteogenic differentiation marker Ca2+. Full article
(This article belongs to the Section Biomaterials)
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15 pages, 3371 KB  
Article
Electrochemical Radical Tandem Difluoroethylation/Cyclization of Unsaturated Amides to Access MeCF2-Featured Indolo/Benzoimidazo [2,1-a]Isoquinolin-6(5H)-ones
by Yunfei Tian, Dongyu Guo, Luping Zheng, Shaolu Yang, Ningning Zhang, Weijun Fu and Zejiang Li
Molecules 2024, 29(5), 973; https://doi.org/10.3390/molecules29050973 - 22 Feb 2024
Cited by 3 | Viewed by 1921
Abstract
A metal-free electrochemical oxidative difluoroethylation of 2-arylbenzimidazoles was accomplished, which provided an efficient strategy for the synthesis of MeCF2-containing benzo[4,5]imidazo[2,1-a]-isoquinolin-6(5H)-ones. In addition, the method also enabled the efficient construction of various difluoroethylated indolo[2,1-a]isoquinolin-6(5H)-ones. [...] Read more.
A metal-free electrochemical oxidative difluoroethylation of 2-arylbenzimidazoles was accomplished, which provided an efficient strategy for the synthesis of MeCF2-containing benzo[4,5]imidazo[2,1-a]-isoquinolin-6(5H)-ones. In addition, the method also enabled the efficient construction of various difluoroethylated indolo[2,1-a]isoquinolin-6(5H)-ones. Notably, this electrochemical synthesis protocol proceeded well under mild conditions without metal catalysts or exogenous additives/oxidants added. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Synthesis)
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20 pages, 2912 KB  
Article
Synthesis of New Triazolopyrazine Antimalarial Compounds
by Daniel J. G. Johnson, Ian D. Jenkins, Cohan Huxley, Mark J. Coster, Kah Yean Lum, Jonathan M. White, Vicky M. Avery and Rohan A. Davis
Molecules 2021, 26(9), 2421; https://doi.org/10.3390/molecules26092421 - 21 Apr 2021
Cited by 9 | Viewed by 6157
Abstract
A radical approach to late-stage functionalization using photoredox and Diversinate chemistry on the Open Source Malaria (OSM) triazolopyrazine scaffold (Series 4) resulted in the synthesis of 12 new analogues, which were characterized by NMR, UV, and MS data analysis. The structures of [...] Read more.
A radical approach to late-stage functionalization using photoredox and Diversinate chemistry on the Open Source Malaria (OSM) triazolopyrazine scaffold (Series 4) resulted in the synthesis of 12 new analogues, which were characterized by NMR, UV, and MS data analysis. The structures of four triazolopyrazines were confirmed by X-ray crystal structure analysis. Several minor and unexpected side products were generated during these studies, including two resulting from a possible disproportionation reaction. All compounds were tested for their ability to inhibit the growth of the malaria parasite Plasmodium falciparum (3D7 and Dd2 strains) and for cytotoxicity against a human embryonic kidney (HEK293) cell line. Moderate antimalarial activity was observed for some of the compounds, with IC50 values ranging from 0.3 to >20 µM; none of the compounds displayed any toxicity against HEK293 at 80 µM. Full article
(This article belongs to the Special Issue Organic Synthesis in Drug Discovery)
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17 pages, 4645 KB  
Article
Internal Structure of Thermoresponsive Physically Crosslinked Nanogel of Poly[N-(2-hydroxypropyl)methacrylamide]-Block-Poly[N-(2,2-difluoroethyl)acrylamide], Prominent 19F MRI Tracer
by David Babuka, Kristyna Kolouchova, Ondrej Groborz, Zdenek Tosner, Alexander Zhigunov, Petr Stepanek and Martin Hruby
Nanomaterials 2020, 10(11), 2231; https://doi.org/10.3390/nano10112231 - 10 Nov 2020
Cited by 16 | Viewed by 3816
Abstract
Fluorine-19 MRI is a promising noninvasive diagnostic method. However, the absence of a nontoxic fluorine-19 MRI tracer that does not suffer from poor biodistribution as a result of its strong fluorophilicity is a constant hurdle in the widespread applicability of this otherwise versatile [...] Read more.
Fluorine-19 MRI is a promising noninvasive diagnostic method. However, the absence of a nontoxic fluorine-19 MRI tracer that does not suffer from poor biodistribution as a result of its strong fluorophilicity is a constant hurdle in the widespread applicability of this otherwise versatile diagnostic technique. The poly[N-(2-hydroxypropyl)methacrylamide]-block-poly[N-(2,2-difluoroethyl)acrylamide] thermoresponsive copolymer was proposed as an alternative fluorine-19 MRI tracer capable of overcoming such shortcomings. In this paper, the internal structure of self-assembled particles of this copolymer was investigated by various methods including 1D and 2D NMR, dynamic light scattering (DLS), small-angle X-ray scattering (SAXS) and small-angle neutron scattering (SANS). The elucidated structure appears to be that of a nanogel with greatly swollen hydrophilic chains and tightly packed thermoresponsive chains forming a network within the nanogel particles, which become more hydrophobic with increasing temperature. Its capacity to provide a measurable fluorine-19 NMR signal in its aggregated state at human body temperature was also investigated and confirmed. This capacity stems from the different fluorine-19 nuclei relaxation properties compared to those of hydrogen-1 nuclei. Full article
(This article belongs to the Special Issue Frontiers in Nanomaterials for Clinical Imaging and Selective Therapy)
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