Nucleolipids of Canonical Purine ss-d-Ribo-Nucleosides: Synthesis and Cytostatic/Cytotoxic Activities Toward Human and Rat Glioblastoma Cells

DC FieldValueLanguage
dc.contributor.authorKnies, Christine
dc.contributor.authorHammerbacher, Katharina
dc.contributor.authorBonaterra, Gabriel A.
dc.contributor.authorKinscherf, Ralf
dc.contributor.authorRosemeyer, Helmut
dc.date.accessioned2021-12-23T16:10:36Z-
dc.date.available2021-12-23T16:10:36Z-
dc.date.issued2016
dc.identifier.issn21911363
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/9312-
dc.description.abstractWe report on the synthesis of two series of canonical purine ss-d-ribonucleoside nucleolipids derived from inosine and adenosine, which have been characterized by elemental analyses, electrospray ionization mass spectrometry (ESI MS) as well as by H-1 and (CNMR)-C-13, and pH-dependent UV/Vis spectroscopy. A selection of the novel nucleolipids with different lipophilic moieties were first tested on their cytotoxic effect toward human macrophages. Compounds without a significant inhibitory effect on the viability of the macrophages were tested on their cytostatic/cytotoxic effect toward human astrocytoma/oligodendroglioma GOS-3 cells as well as against the rat malignant neuroectodermal BT4Ca cell line. In order to additionally investigate the potential molecular mechanisms involved in the cytotoxic effects of the derivatives on GOS-3 or BT4Ca cells, we evaluated the induction of apoptosis and observed the particular activity of the nucleolipid ethyl 3-{4-hydroxymethyl-2-methyl-6-[6-oxo-1-(3,7,11-trimethyl-dodeca-2,6,1 0-trienyl)-1,6-dihydro-purin-9-yl]-tetrahydro-furo[3,4-d][1,3]dioxol -2-yl}propionate (8c) toward both human and rat glioblastoma cell lines invitro.
dc.description.sponsorshipBundesministerium fur Wirtschaft, Germany [FKZ: KF 2369401 SB9, FKZ 2369501 SB9]; The authors thank the following University of Osnabruck and Marburg members: Marianne Gather Steckhan for the NMR measurements, Dr. Stefan Walter for HR ESI MS, Anja Schuster for the elemental analyses, Petra Basel for formulae drawings, Henning Eickmeier and Holger Heine for the preparation of Figure 3 (Univerity of Osnabruck); Andrea Cordes, Elke Volck-Badouin (University of Marburg); Diana Yudin and Anna Diestel (University of Osnabruck) for valuable technical assistance; as well as Ellen Essen and Gabriella Stauch (University of Marburg) for preparation of the manuscript. The authors also gratefully acknowledge financial support by the Bundesministerium fur Wirtschaft, Germany (FKZ: KF 2369401 SB9 and FKZ 2369501 SB9). Moreover, the authors thank Prof. Dr. Uwe Beginn for excellent laboratory facilities at the University of Osnabruck.
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.relation.ispartofCHEMISTRYOPEN
dc.subjectADENOSINE-DEAMINASE
dc.subjectAFFINITY RESINS
dc.subjectANALOGS
dc.subjectantitumor agents
dc.subjectCARCINOMA CELLS
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectCOLON
dc.subjectcytotoxicity
dc.subjectDERIVATIVES
dc.subjectglioblastomas
dc.subjectIDENTIFICATION
dc.subjectINOSINE
dc.subjectketal lipophilicity
dc.subjectLIPOPHILIZATION
dc.subjectnucleolipids
dc.subjectOLIGONUCLEOTIDES
dc.subjectprenylation
dc.titleNucleolipids of Canonical Purine ss-d-Ribo-Nucleosides: Synthesis and Cytostatic/Cytotoxic Activities Toward Human and Rat Glioblastoma Cells
dc.typejournal article
dc.identifier.doi10.1002/open.201500197
dc.identifier.isiISI:000374711500006
dc.description.volume5
dc.description.issue2
dc.description.startpage129
dc.description.endpage141
dc.contributor.researcheridAAV-7164-2021
dc.publisher.placePOSTFACH 101161, 69451 WEINHEIM, GERMANY
dcterms.isPartOf.abbreviationChemistryOpen
dcterms.oaStatusgold, Green Published
crisitem.author.deptInstitut für Chemie neuer Materialien-
crisitem.author.deptidinstitute11-
crisitem.author.parentorgFB 05 - Biologie/Chemie-
crisitem.author.grandparentorgUniversität Osnabrück-
crisitem.author.netidRoHe783-
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