Huayang Feng, Jürgen Linders, Miriam Cantore, Jonas Fabrizi, Annika Kirsten, Sascha Myszkowska, Eva Hillen, Florian Uteschil, Sebastian Buchholz, Andrea Hermsen, Maria Davila Garvin, Katja Bettina Ferenz, Christian Mayer
Perfluorodecalin (PFD)-filled capsules have been studied for over 15 years as artificial oxygen carriers. However, none of these capsules combines good biocompatibility, good mechanical stability and dispersion stability. Here we propose to use synthetic triblock peptides containing a central block of cysteine units as a cross-linking shell material for capsules with both good biocompatibility and stability. Together with outer aspartate units and inner phenylalanine units, the resulting amphiphilic triblock peptides can encapsulate PFD efficiently to prepare capsules with a suitable diameter, a certain mechanical strength, a large diffusion constant, fast gas exchange rates, and little cytotoxicity. Given the above advantages, these PFD-filled peptide capsules are very promising as potential artificial oxygen carriers.
{"title":"Cross-linked Triblock Peptide Capsules as Potential Oxygen Carriers","authors":"Huayang Feng, Jürgen Linders, Miriam Cantore, Jonas Fabrizi, Annika Kirsten, Sascha Myszkowska, Eva Hillen, Florian Uteschil, Sebastian Buchholz, Andrea Hermsen, Maria Davila Garvin, Katja Bettina Ferenz, Christian Mayer","doi":"10.1002/open.202300282","DOIUrl":"10.1002/open.202300282","url":null,"abstract":"<p>Perfluorodecalin (PFD)-filled capsules have been studied for over 15 years as artificial oxygen carriers. However, none of these capsules combines good biocompatibility, good mechanical stability and dispersion stability. Here we propose to use synthetic triblock peptides containing a central block of cysteine units as a cross-linking shell material for capsules with both good biocompatibility and stability. Together with outer aspartate units and inner phenylalanine units, the resulting amphiphilic triblock peptides can encapsulate PFD efficiently to prepare capsules with a suitable diameter, a certain mechanical strength, a large diffusion constant, fast gas exchange rates, and little cytotoxicity. Given the above advantages, these PFD-filled peptide capsules are very promising as potential artificial oxygen carriers.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-03-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/open.202300282","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140109520","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Dr. Yichuan Wang, Yuting Li, Dr. Olaf Fuhr, Dr. Martin Nieger, Dr. Zahid Hassan, Prof. Dr. Stefan Bräse
In this report, a new series of mono-, di-, tri-, and tetra-cationic pyridinium and vinyl pyridinium-modified [2.2]paracyclophanes as useful molecular tectons for supramolecular systems are described. Regioselective functionalization at specific positions, followed by resolution step and successive transformations through Pd-catalyzed Suzuki-Miyaura and Mizoroki-Heck cross-coupling chemistry furnish a series of modular PCP scaffolds. In our proof-of-concept study, on N-methylation, the PCPs bearing (cationic) pyridyl functionalities were demonstrated as useful molecular receptors in host-guest supramolecular assays. The PCPs on grafting with light-responsive azobenzene (−N=N−) functional core as side-groups impart photosensitivity that can be remotely transformed on irradiation, offering photo-controlled smart molecular functions. Furthermore, the symmetrical PCPs bearing bi-, and tetra-pyridyl functionalities at the peripheries have enormous potential to serve as ditopic and tetratopic 3D molecular tectons for engineering non-covalent supramolecular assemblies with new structural and functional attributes.
{"title":"Synthesis of Mono-, Di-, Tri-, and Tetra-cationic Pyridinium and Vinylpyridinium Modified [2.2]Paracyclophanes: Modular Receptors for Supramolecular Systems","authors":"Dr. Yichuan Wang, Yuting Li, Dr. Olaf Fuhr, Dr. Martin Nieger, Dr. Zahid Hassan, Prof. Dr. Stefan Bräse","doi":"10.1002/open.202400024","DOIUrl":"10.1002/open.202400024","url":null,"abstract":"<p>In this report, a new series of mono-, di-, tri-, and tetra-cationic pyridinium and vinyl pyridinium-modified [2.2]paracyclophanes as useful molecular tectons for supramolecular systems are described. Regioselective functionalization at specific positions, followed by resolution step and successive transformations through Pd-catalyzed Suzuki-Miyaura and Mizoroki-Heck cross-coupling chemistry furnish a series of modular PCP scaffolds. In our proof-of-concept study, on <i>N</i>-methylation, the PCPs bearing (cationic) pyridyl functionalities were demonstrated as useful molecular receptors in host-guest supramolecular assays. The PCPs on grafting with light-responsive azobenzene (−N=N−) functional core as side-groups impart photosensitivity that can be remotely transformed on irradiation, offering photo-controlled smart molecular functions. Furthermore, the symmetrical PCPs bearing bi-, and tetra-pyridyl functionalities at the peripheries have enormous potential to serve as ditopic and tetratopic 3D molecular tectons for engineering non-covalent supramolecular assemblies with new structural and functional attributes.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-03-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/open.202400024","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140109521","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Saponins are glycosides widely distributed in the plant kingdom and have many pharmacological activities. However, their tendency to bind to cell membranes can cause cell rupture, limiting their clinical use. In the previous study, aristatoside C and davisianoside B were isolated from Cephalaria species. Cytotoxicity assays showed that they are more active on A-549 cell lines than doxorubicin but caused hemolysis. In the current research, aristatoside C and davisianoside B were loaded to phytosomes called ALPs and DLPs respectively, and characterized for particle size, zeta potential, encapsulation efficiency, release kinetic, hemolytic activity, and cytotoxicity on A-549 cell line. DLPs maintained the cytotoxic activity of the free saponins against A-549 cells with IC50 of 9,64±0,02 μg/ml but dramatically reduced their hemolytic activity. Furthermore, temperature and time-dependent stability studies based on the size and zeta potential of ALPs and DLPs revealed that the phytosomes have sustained release properties over 2 weeks. Overall, DLPs displayed cytotoxicity against A-549 cells with minimal hemolysis and sustained release, highlighting their potential as nanotherapeutics for clinical applications.
皂苷是广泛分布于植物界的苷类化合物,具有多种药理活性。然而,它们与细胞膜结合的倾向会导致细胞破裂,从而限制了它们在临床上的应用。在之前的研究中,我们从头花科植物中分离出了 aristatoside C 和 davisianoside B。细胞毒性试验表明,与多柔比星相比,它们对 A-549 细胞株更有活性,但会引起溶血。目前的研究将阿里斯他苷 C 和戴维仙苷 B 分别载入名为 ALPs 和 DLPs 的植物体中,并对其粒径、ZETA电位、包封效率、释放动力学、溶血活性以及对 A-549 细胞株的细胞毒性进行了表征。DLPs保持了游离皂甙对A-549细胞的细胞毒活性,IC50为9,64±0,02 μg/ml,但大大降低了其溶血活性。此外,根据 ALPs 和 DLPs 的大小和 zeta 电位进行的温度和时间依赖性稳定性研究表明,植物体具有持续释放特性,释放时间超过 2 周。总之,DLPs对A-549细胞具有细胞毒性,溶血作用极小,且可持续释放,这凸显了它们作为纳米治疗药物在临床应用方面的潜力。
{"title":"Development and Characterization of Plant-derived Aristatoside C and Davisianoside B Saponin-loaded Phytosomes with Suppressed Hemolytic Activity.","authors":"Sebnem Ercelen, Bunyamin Bulkurcuoglu, Mustafa Oksuz, Ayse Nalbantsoy, Nazli Boke Sarikahya","doi":"10.1002/open.202300254","DOIUrl":"10.1002/open.202300254","url":null,"abstract":"<p><p>Saponins are glycosides widely distributed in the plant kingdom and have many pharmacological activities. However, their tendency to bind to cell membranes can cause cell rupture, limiting their clinical use. In the previous study, aristatoside C and davisianoside B were isolated from Cephalaria species. Cytotoxicity assays showed that they are more active on A-549 cell lines than doxorubicin but caused hemolysis. In the current research, aristatoside C and davisianoside B were loaded to phytosomes called ALPs and DLPs respectively, and characterized for particle size, zeta potential, encapsulation efficiency, release kinetic, hemolytic activity, and cytotoxicity on A-549 cell line. DLPs maintained the cytotoxic activity of the free saponins against A-549 cells with IC50 of 9,64±0,02 μg/ml but dramatically reduced their hemolytic activity. Furthermore, temperature and time-dependent stability studies based on the size and zeta potential of ALPs and DLPs revealed that the phytosomes have sustained release properties over 2 weeks. Overall, DLPs displayed cytotoxicity against A-549 cells with minimal hemolysis and sustained release, highlighting their potential as nanotherapeutics for clinical applications.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":null,"pages":null},"PeriodicalIF":2.3,"publicationDate":"2024-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140093494","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
This research article uses density functional theory (DFT) to study photoinduced borylation. This work examined the electron donor-acceptor complex (EDA) of bis(catecholato)diboron with different redox-active leaving groups and bis(pinacol)diboron with aryl N-hydroxyphthalimide. The results of these DFT studies show the complex ratio of B2cat2 and N, N-dimethylacetamide (DMA) should be 1 : 2 which is consistent with the experimental results in the literature. We further proposed a reaction mechanism and calculated the energies associated with each step.
{"title":"A Computational Study of Photoinduced Borylation for Selected Boron Sources","authors":"Ka Wa Fan, Hoi Ling Luk, Prof. David Lee Phillips","doi":"10.1002/open.202300285","DOIUrl":"10.1002/open.202300285","url":null,"abstract":"<p>This research article uses density functional theory (DFT) to study photoinduced borylation. This work examined the electron donor-acceptor complex (EDA) of bis(catecholato)diboron with different redox-active leaving groups and bis(pinacol)diboron with aryl N-hydroxyphthalimide. The results of these DFT studies show the complex ratio of B<sub>2</sub>cat<sub>2</sub> and N, N-dimethylacetamide (DMA) should be 1 : 2 which is consistent with the experimental results in the literature. We further proposed a reaction mechanism and calculated the energies associated with each step.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-03-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11230929/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140058767","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}