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

Autor(en): Knies, Christine
Hammerbacher, Katharina
Bonaterra, Gabriel A.
Kinscherf, Ralf
Rosemeyer, Helmut 
Stichwörter: ADENOSINE-DEAMINASE; AFFINITY RESINS; ANALOGS; antitumor agents; CARCINOMA CELLS; Chemistry; Chemistry, Multidisciplinary; COLON; cytotoxicity; DERIVATIVES; glioblastomas; IDENTIFICATION; INOSINE; ketal lipophilicity; LIPOPHILIZATION; nucleolipids; OLIGONUCLEOTIDES; prenylation
Erscheinungsdatum: 2016
Volumen: 5
Ausgabe: 2
Startseite: 129
Seitenende: 141
We 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.
ISSN: 21911363
DOI: 10.1002/open.201500197

Show full item record

Google ScholarTM