@article{GonzalezChavarriaDupratRoaetal.2020, author = {Gonzalez-Chavarria, Ivan and Duprat, Felix and Roa, Francisco J. and Jara, Nery and Toledo, Jorge R. and Miranda, Felipe and Becerra, Jose and Inostroza, Alejandro and Kelling, Alexandra and Schilde, Uwe and Heydenreich, Matthias and Paz, Cristian}, title = {Maytenus disticha extract and an isolated β-Dihydroagarofuran induce mitochondrial depolarization and apoptosis in human cancer cells by increasing mitochondrial reactive oxygen species}, series = {Biomolecules}, volume = {10}, journal = {Biomolecules}, number = {3}, publisher = {MDPI}, address = {Basel}, issn = {2218-273X}, doi = {10.3390/biom10030377}, pages = {15}, year = {2020}, abstract = {Maytenus disticha (Hook F.), belonging to the Celastraceae family, is an evergreen shrub, native of the central southern mountains of Chile. Previous studies demonstrated that the total extract of M. disticha (MD) has an acetylcholinesterase inhibitory activity along with growth regulatory and insecticidal activities. beta-Dihydroagarofurans sesquiterpenes are the most active components in the plant. However, its activity in cancer has not been analyzed yet. Here, we demonstrate that MD has a cytotoxic activity on breast (MCF-7), lung (PC9), and prostate (C4-2B) human cancer cells with an IC50 (mu g/mL) of 40, 4.7, and 5 mu g/mL, respectively, an increasing Bax/Bcl2 ratio, and inducing a mitochondrial membrane depolarization. The beta-dihydroagarofuran-type sesquiterpene (MD-6), dihydromyricetin (MD-9), and dihydromyricetin-3-O-beta-glucoside (MD-10) were isolated as the major compounds from MD extracts. From these compounds, only MD-6 showed cytotoxic activity on MCF-7, PC9, and C4-2B with an IC50 of 31.02, 17.58, and 42.19 mu M, respectively. Furthermore, the MD-6 increases cell ROS generation, and MD and MD-6 induce a mitochondrial superoxide generation and apoptosis on MCF-7, PC9, and C4-2B, which suggests that the cytotoxic effect of MD is mediated in part by the beta-dihydroagarofuran-type that induces apoptosis by a mitochondrial dysfunction.}, language = {en} } @misc{KruegerKellingLinkeretal.2019, author = {Krueger, Tobias and Kelling, Alexandra and Linker, Torsten and Schilde, Uwe}, title = {Crystal structures of three cyclohexane‑based γ‑spirolactams}, series = {Postprints der Universit{\"a}t Potsdam Mathematisch-Naturwissenschaftliche Reihe}, journal = {Postprints der Universit{\"a}t Potsdam Mathematisch-Naturwissenschaftliche Reihe}, number = {738}, doi = {10.25932/publishup-43491}, url = {http://nbn-resolving.de/urn:nbn:de:kobv:517-opus4-434911}, pages = {9}, year = {2019}, abstract = {The title compounds, 2-azaspiro[4.5]deca-1-one, C₉H₁₅NO, (1a), cis-8-methyl-2-azaspiro[4.5]deca-1-one, C₁₀H₁₇NO, (1b), and trans-8-methyl-2-azaspiro[4.5]deca-1-one, C₁₀H₁₇NO, (1c), were synthesized from benzoic acids 2 in only 3 steps in high yields. Crystallization from n-hexane afforded single crystals, suitable for X-ray diffraction. Thus, the configurations, conformations, and interesting crystal packing effects have been determined unequivocally. The bicyclic skeleton consists of a lactam ring, attached by a spiro junction to a cyclohexane ring. The lactam ring adopts an envelope conformation and the cyclohexane ring has a chair conformation. The main difference between compound 1b and compound 1c is the position of the carbonyl group on the 2-pyrrolidine ring with respect to the methyl group on the 8-position of the cyclohexane ring, which is cis (1b) or trans (1c). A remarkable feature of all three compounds is the existence of a mirror plane within the molecule. Given that all compounds crystallize in centrosymmetric space groups, the packing always contains interesting enantiomer-like pairs. Finally, the structures are stabilized by intermolecular N-H···O hydrogen bonds.}, language = {en} } @misc{KirsteBrietzkeHoldtetal.2019, author = {Kirste, Matthias and Brietzke, Thomas Martin and Holdt, Hans-J{\"u}rgen and Schilde, Uwe}, title = {The crystal structure of 1,12-diazaperylene, C₁₈H₁₀N₂}, series = {Postprints der Universit{\"a}t Potsdam Mathematisch-Naturwissenschaftliche Reihe}, journal = {Postprints der Universit{\"a}t Potsdam Mathematisch-Naturwissenschaftliche Reihe}, number = {752}, issn = {1866-8372}, doi = {10.25932/publishup-43650}, url = {http://nbn-resolving.de/urn:nbn:de:kobv:517-opus4-436501}, pages = {3}, year = {2019}, abstract = {C₁₈H₁₀N₂, monoclinic, P2₁/c (no. 14), a=7.9297(9) {\AA}, b=11.4021(14) {\AA}, c=13.3572(15) {\AA}, β=105.363(8)°, V =1164.5(2) {\AA}³, Z =4, Rgt(F)=0.0325, wRref(F²)=0.0774, T =210(2) K.}, language = {en} } @article{KirsteBrietzkeHoldtetal.2019, author = {Kirste, Matthias and Brietzke, Thomas Martin and Holdt, Hans-J{\"u}rgen and Schilde, Uwe}, title = {The crystal structure of 1,12-diazaperylene, C₁₈H₁₀N₂}, series = {Zeitschrift f{\"u}r Kristallographie - New Crystal Structures}, volume = {234}, journal = {Zeitschrift f{\"u}r Kristallographie - New Crystal Structures}, number = {6}, publisher = {De Gruyter}, address = {Berlin}, issn = {2196-7105}, doi = {10.1515/NCRS-2019-0385}, pages = {1255 -- 1257}, year = {2019}, abstract = {C₁₈H₁₀N₂, monoclinic, P2₁/c (no. 14), a=7.9297(9) {\AA}, b=11.4021(14) {\AA}, c=13.3572(15) {\AA}, β=105.363(8)°, V =1164.5(2) {\AA}³, Z =4, Rgt(F)=0.0325, wRref(F²)=0.0774, T =210(2) K.}, language = {en} } @article{KruegerKellingLinkeretal.2019, author = {Krueger, Tobias and Kelling, Alexandra and Linker, Torsten and Schilde, Uwe}, title = {Crystal structures of three cyclohexane‑based γ‑spirolactams}, series = {BMC Chemistry}, volume = {13}, journal = {BMC Chemistry}, number = {69}, publisher = {Springer International Publishing}, address = {Basel}, issn = {2661-801X}, doi = {10.1186/s13065-019-0586-7}, pages = {9}, year = {2019}, abstract = {The title compounds, 2-azaspiro[4.5]deca-1-one, C₉H₁₅NO, (1a), cis-8-methyl-2-azaspiro[4.5]deca-1-one, C₁₀H₁₇NO, (1b), and trans-8-methyl-2-azaspiro[4.5]deca-1-one, C₁₀H₁₇NO, (1c), were synthesized from benzoic acids 2 in only 3 steps in high yields. Crystallization from n-hexane afforded single crystals, suitable for X-ray diffraction. Thus, the configurations, conformations, and interesting crystal packing effects have been determined unequivocally. The bicyclic skeleton consists of a lactam ring, attached by a spiro junction to a cyclohexane ring. The lactam ring adopts an envelope conformation and the cyclohexane ring has a chair conformation. The main difference between compound 1b and compound 1c is the position of the carbonyl group on the 2-pyrrolidine ring with respect to the methyl group on the 8-position of the cyclohexane ring, which is cis (1b) or trans (1c). A remarkable feature of all three compounds is the existence of a mirror plane within the molecule. Given that all compounds crystallize in centrosymmetric space groups, the packing always contains interesting enantiomer-like pairs. Finally, the structures are stabilized by intermolecular N-H···O hydrogen bonds.}, language = {en} } @article{AlrefaiMondalWrucketal.2019, author = {Alrefai, Anas and Mondal, Suvendu Sekhar and Wruck, Alexander and Kelling, Alexandra and Schilde, Uwe and Brandt, Philipp and Janiak, Christoph and Schoenfeld, Sophie and Weber, Birgit and Rybakowski, Lawrence and Herrman, Carmen and Brennenstuhl, Katlen and Eidner, Sascha and Kumke, Michael Uwe and Behrens, Karsten and G{\"u}nter, Christina and M{\"u}ller, Holger and Holdt, Hans-J{\"u}rgen}, title = {Hydrogen-bonded supramolecular metal-imidazolate frameworks: gas sorption, magnetic and UV/Vis spectroscopic properties}, series = {Journal of Inclusion Phenomena and Macrocyclic Chemistry}, volume = {94}, journal = {Journal of Inclusion Phenomena and Macrocyclic Chemistry}, number = {3-4}, publisher = {Springer}, address = {Dordrecht}, issn = {1388-3127}, doi = {10.1007/s10847-019-00926-6}, pages = {155 -- 165}, year = {2019}, abstract = {By varying reaction parameters for the syntheses of the hydrogen-bonded metal-imidazolate frameworks (HIF) HIF-1 and HIF-2 (featuring 14 Zn and 14 Co atoms, respectively) to increase their yields and crystallinity, we found that HIF-1 is generated in two different frameworks, named as HIF-1a and HIF-1b. HIF-1b is isostructural to HIF-2. We determined the gas sorption and magnetic properties of HIF-2. In comparison to HIF-1a (Brunauer-Emmett-Teller (BET) surface area of 471m(2) g(-1)), HIF-2 possesses overall very low gas sorption uptake capacities [BET(CO2) surface area=85m(2) g(-1)]. Variable temperature magnetic susceptibility measurement of HIF-2 showed antiferromagnetic exchange interactions between the cobalt(II) high-spin centres at lower temperature. Theoretical analysis by density functional theory confirmed this finding. The UV/Vis-reflection spectra of HIF-1 (mixture of HIF-1a and b), HIF-2 and HIF-3 (with 14 Cd atoms) were measured and showed a characteristic absorption band centered at 340nm, which was indicative for differences in the imidazolate framework.}, language = {en} } @article{SardarianInalooModarresiAlametal.2019, author = {Sardarian, Ali Reza and Inaloo, Iman Dindarloo and Modarresi-Alam, Ali Reza and Kleinpeter, Erich and Schilde, Uwe}, title = {Metal-Free Regioselective Monocyanation of Hydroxy-, Alkoxy-, and Benzyloxyarenes by Potassium Thiocyanate and Silica Sulfuric Acid as a Cyanating Agent}, series = {The journal of organic chemistry}, volume = {84}, journal = {The journal of organic chemistry}, number = {4}, publisher = {American Chemical Society}, address = {Washington}, issn = {0022-3263}, doi = {10.1021/acs.joc.8b02191}, pages = {1748 -- 1756}, year = {2019}, abstract = {A novel and efficient metal- and solvent-free regioselective para-C-H cyanation of hydroxy-, alkoxy-, and benzyloxyarene derivatives has been introduced, using nontoxic potassium thiocyanate as a cyanating reagent in the presence of silica sulfuric acid (SSA). The desired products are obtained in good to high yields without any toxic byproducts.}, language = {en} } @article{LeeHwangSchildeetal.2018, author = {Lee, Hui-Chun and Hwang, Jongkook and Schilde, Uwe and Antonietti, Markus and Matyjaszewski, Krzysztof and Schmidt, Bernhard V. K. J.}, title = {Toward ultimate control of radical polymerization}, series = {Chemistry of materials : a publication of the American Chemical Society}, volume = {30}, journal = {Chemistry of materials : a publication of the American Chemical Society}, number = {9}, publisher = {American Chemical Society}, address = {Washington}, issn = {0897-4756}, doi = {10.1021/acs.chemmater.8b00546}, pages = {2983 -- 2994}, year = {2018}, abstract = {Herein, an approach via combination of confined porous textures and reversible deactivation radical polymerization techniques is proposed to advance synthetic polymer chemistry, i.e., a connection of metal-organic frameworks (MOFs) and activators regenerated by electron transfer atom transfer radical polymerization (ARGET ATRP). Zn-2(benzene-1,4-dicarboxylate)2(1,4-diazabicyclo[2.2.2]-octane) [Zn-2(bdc)(2)(dabco)] is utilized as a reaction environment for polymerization of various methacrylate monomers (methyl, ethyl, benzyl, and isobornyl methacrylate) in a confined nanochannel, resulting in polymers with control over dispersity, end functionalities, and tacticity with respect to distinct molecular size. To refine and reconsolidate the compartmentation effect on polymer regularity, initiator-functionalized Zn MOF was synthesized via cocrystallization with an initiator-functionalized ligand, 2-(2-bromo-2-methylpropanamido)-1,4-benzenedicarboxylate (Brbdc), in different ratios (10\%, 20\%, and 50\%). Through the embedded initiator, surface-initiated ARGET ATRP was directly initiated from the walls of the nanochannels. The obtained polymers had a high molecular weight up to 392 000. Moreover, a significant improvement in end-group functionality and stereocontrol was observed, entailing polymers with obvious increments in isotacticity. The results highlight a combination of MOFs and ATRP that is a promising and universal methodology to prepare various polymers with high molecular weight exhibiting well-defined uniformity in chain length and microstructure as well as the preserved chain-end functionality.}, language = {en} } @misc{GrunwaldKellingHoldtetal.2017, author = {Grunwald, Nicolas and Kelling, Alexandra and Holdt, Hans-J{\"u}rgen and Schilde, Uwe}, title = {The crystal structure of 1,1′-bisisoquinoline, C18H12N2}, url = {http://nbn-resolving.de/urn:nbn:de:kobv:517-opus4-401952}, pages = {3}, year = {2017}, abstract = {C18H12N2, tetragonal, I41/a (no. 88), a=13.8885(6) {\AA}, c=13.6718(6) {\AA}, V =2637.2(3) {\AA}3, Z =8, Rgt(F)=0.0295, wRref(F2)=0.0854, T =210 K. CCDC no.: 631823}, language = {en} } @article{GrunwaldKellingHoldtetal.2017, author = {Grunwald, Nicolas and Kelling, Alexandra and Holdt, Hans-J{\"u}rgen and Schilde, Uwe}, title = {The crystal structure of 1,1′-bisisoquinoline, C18H12N2}, series = {Zeitschrift f{\"u}r Kristallographie : international journal for structural, physical and chemical aspects of crystalline materials. New crystal structures}, volume = {232}, journal = {Zeitschrift f{\"u}r Kristallographie : international journal for structural, physical and chemical aspects of crystalline materials. New crystal structures}, number = {5}, publisher = {de Gruyter}, address = {Berlin}, doi = {10.1515/ncrs-2017-0088}, pages = {839 -- 841}, year = {2017}, abstract = {C18H12N2, tetragonal, I41/a (no. 88), a=13.8885(6) {\AA}, c=13.6718(6) {\AA}, V =2637.2(3) {\AA}3, Z =8, Rgt(F)=0.0295, wRref(F2)=0.0854, T =210 K. CCDC no.: 631823}, language = {en} }