Novel Nucleolipids of Pyrimidine beta-D-Ribonucleosides: Combinatorial Synthesis, Spectroscopic Characterization, and Cytostatic/Cytotoxic Activities
DC Element | Wert | Sprache |
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dc.contributor.author | Knies, Christine | |
dc.contributor.author | Hammerbacher, Katharina | |
dc.contributor.author | Bonaterra, Gabriel A. | |
dc.contributor.author | Kinscherf, Ralf | |
dc.contributor.author | Rosemeyer, Helmut | |
dc.date.accessioned | 2021-12-23T16:06:56Z | - |
dc.date.available | 2021-12-23T16:06:56Z | - |
dc.date.issued | 2016 | |
dc.identifier.issn | 16121872 | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/7625 | - |
dc.description.abstract | Four series of nucleolipids with either uridine, 5-methyluridine, 5-fluorouridine, and 6-azauridine as -D-ribonucleoside component have been prepared in a combinatorial (not parallel!) manner (see Formulae). All compounds have been characterized by elemental analyses, ESI mass spectrometry as well as by H-1-, and C-13-NMR, and UV spectroscopy. A selection of eight nucleolipids with different lipophilizing moieties, based on earlier findings, as well as of 5-fluorouridine as control were first tested on their cytotoxic effect towards PMA-differentiated human THP-1 macrophages. Those compounds which did not exhibit a significant inhibitory effect on the survival of the macrophages were next tested on their cytostatic/cytotoxic effect towards the human astrocytoma/oligodendroglioma GOS-3 cells as well as against the rat malignant neuroectodermal BT4Ca cell line. Additionally, induction of apoptosis of the cell lines was evaluated. It turned out that particularly a combined lipophilization of the nucleosides by an 2,3-O-ethyl levulinate residue plus a farnesyl moiety at N(3) of the pyrimidine moiety of the corresponding nucleolipids leads to an active compound with the highest probability. | |
dc.description.sponsorship | Bundesministerium fur Wirtschaft [FKZ: KF 2369401 S B9, FKZ 2369501 SB9]; The authors thank Mrs. Marianne Gather Steckhan for the NMR measurements, Dr. Stefan Walter for ESI mass spectra, Mrs. Anja Schuster for the elemental analyses. Mrs. Petra Boesel for formulae drawings, Mrs. Andrea Cordes, Mrs. Elke Volck-Badouin, Mrs. Janina Meyer, Mrs. Julia ThomBen, Mrs. Tatjana Abakumov, Mrs. Katharina Goertemaker, Mrs. Johanna Schmidtmann, for valuable technical assistance, and Prof. Dr. Evelyn Lescrinier for valuable discussions. We also gratefully acknowledge financial support by the Bundesministerium fur Wirtschaft (FKZ: KF 2369401 S B9 and FKZ 2369501 SB9). Moreover, we thank Prof. Dr. Uwe Beginn for excellent laboratory facilities. | |
dc.language.iso | en | |
dc.publisher | WILEY-V C H VERLAG GMBH | |
dc.relation.ispartof | CHEMISTRY & BIODIVERSITY | |
dc.subject | 5-FLUOROURIDINE | |
dc.subject | ACETAL DERIVATIVES | |
dc.subject | ADENOSINE | |
dc.subject | Biochemistry & Molecular Biology | |
dc.subject | BT4Ca | |
dc.subject | BUILDING-BLOCKS | |
dc.subject | CARCINOMA CELLS | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Multidisciplinary | |
dc.subject | Combinatorial synthesis | |
dc.subject | Cytostatic | |
dc.subject | cytotoxic activity | |
dc.subject | DRUG | |
dc.subject | GOS-3 | |
dc.subject | IDENTIFICATION | |
dc.subject | IMMOBILIZATION | |
dc.subject | LIPOPHILIZATION | |
dc.subject | Nucleolipids | |
dc.subject | NUCLEOSIDES | |
dc.subject | THP-1 | |
dc.title | Novel Nucleolipids of Pyrimidine beta-D-Ribonucleosides: Combinatorial Synthesis, Spectroscopic Characterization, and Cytostatic/Cytotoxic Activities | |
dc.type | journal article | |
dc.identifier.doi | 10.1002/cbdv.201500158 | |
dc.identifier.isi | ISI:000370739300003 | |
dc.description.volume | 13 | |
dc.description.issue | 2 | |
dc.description.startpage | 160 | |
dc.description.endpage | 180 | |
dc.contributor.researcherid | AAV-7164-2021 | |
dc.identifier.eissn | 16121880 | |
dc.publisher.place | POSTFACH 101161, 69451 WEINHEIM, GERMANY | |
dcterms.isPartOf.abbreviation | Chem. Biodivers. | |
crisitem.author.dept | Institut für Chemie neuer Materialien | - |
crisitem.author.deptid | institute11 | - |
crisitem.author.parentorg | FB 05 - Biologie/Chemie | - |
crisitem.author.grandparentorg | Universität Osnabrück | - |
crisitem.author.netid | RoHe783 | - |
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geprüft am 07.06.2024