Nucleophilic additions on α,β-unsaturated keto-nucleosides: preparation of 2-amino-2-deoxy- and 2-thio-hexopyranos-4-ulose nucleosides

Herscovici, Jean; Argoullon, Jean-Michel; Egron, Marie-José; Antonakis, Kostas

doi:10.1016/0008-6215(83)88294-9

Cited by 9 publications

(3 citation statements)

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“…The chemical synthesis and physical properties of ketonucleosides and keto-C-glycosides were reported earlier (7,(13)(14)(15)(16)(17)31). Chemical structures are described in Figure 1.…”

Section: Chemicalsmentioning

confidence: 97%

“…In an effort to design drugs that can overcome common mechanisms of resistance and are suitable for clinical development, we have investigated the design and synthesis of novel nucleoside analogs distinct from gemcitabine or its parent compound, 1-␤-D-arabinofuranosylcytosine. We have previously reported the chemical synthesis (4,6,14,15) and biological activity of unsaturated ketonucleosides in various cellular models (3,13). We have shown that these compounds interact with the sulfhydryl (SH) group of cellular proteins and enzymes (13).…”

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confidence: 99%

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Antiproliferative and Apoptotic Activities of Ketonucleosides and Keto-C-Glycosides against Non-Small-Cell Lung Cancer Cells with Intrinsic Drug Resistance

Paterson

Uriel

Egron

et al. 1998

Antimicrob Agents Chemother

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We compared the biological activity of a new group of keto-C-glycosides to that of a narrow spectrum of unsaturated ketonucleosides in a panel of non-small-cell lung cancer (NSCLC) cells with various levels of intrinsic resistance to standard chemotherapy drugs. Unlike cisplatin, etoposide, adriamycin, or taxol, for which a significant difference in the cytotoxic effect was observed between sensitive cell lines (H460, H125, and MGH4) and drug-resistant cell lines (H661, MGH7, and FADU), nucleoside analogs were equally cytotoxic in NSCLC cell lines, with compound 92 being 10-fold more active than compound 43, 44, 81, or 161, while compound 3 was the least active. Apoptotic measurements with flow cytometric analysis of terminal uridine deoxynucleotide nick end-labeled cells revealed that the cytotoxic activity of these nucleosides correlated with their potency to induce apoptosis. Compound 92 triggered death in cells with wild-type p53, mutated p53, or p53 gene deletion. Our findings suggest that keto-C-glycosides may be promising alternative anticancer agents which merit further studies in in vivo cancer models refractory to standard chemotherapy drugs.

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“…The chemical synthesis and physical properties of ketonucleosides and keto-C-glycosides were reported earlier (7,(13)(14)(15)(16)(17)31). Chemical structures are described in Figure 1.…”

Section: Chemicalsmentioning

confidence: 97%

mentioning

confidence: 99%

Antiproliferative and Apoptotic Activities of Ketonucleosides and Keto-C-Glycosides against Non-Small-Cell Lung Cancer Cells with Intrinsic Drug Resistance

Paterson

Uriel

Egron

et al. 1998

Antimicrob Agents Chemother

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“…Ειδικότερα, νουκλεοζίτες με διακλαδισμένη αλυσίδα στο τμήμα του σακχάρου, καθώς και νουκλεοζίτες που φέρουν αμινοσάκχαρα, λήφθηκαν από τους κετονουκλεοζίτες με απευθείας πυρηνόφιλη προσθήκη (Antonakis and Egron 1973, Halmos and Antonakis 1975, Herscovici et al 1983, Antonakis 1989.…”

Section: κετο-πυρανονουκλεοζίτεςunclassified

Βιοδραστικοί Ακόρεστοι Κετονουκλεοζίτες

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ChemInform Abstract: NUCLEOPHILIC ADDITIONS ON α,β‐UNSATURATED KETONUCLEOSIDES: PREPARATION OF 2‐AMINO‐2‐DEOXY‐ AND 2‐THIOHEXOPYRANOS‐4‐ULOSE NUCLEOSIDES

Herscovici¹,

Argoullon²,

Egron³

et al. 1983

Chemischer Informationsdienst

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Nucleophilic additions on α,β-unsaturated keto-nucleosides: preparation of 2-amino-2-deoxy- and 2-thio-hexopyranos-4-ulose nucleosides

Cited by 9 publications

References 10 publications

Antiproliferative and Apoptotic Activities of Ketonucleosides and Keto-C-Glycosides against Non-Small-Cell Lung Cancer Cells with Intrinsic Drug Resistance

Antiproliferative and Apoptotic Activities of Ketonucleosides and Keto-C-Glycosides against Non-Small-Cell Lung Cancer Cells with Intrinsic Drug Resistance

Βιοδραστικοί Ακόρεστοι Κετονουκλεοζίτες

ChemInform Abstract: NUCLEOPHILIC ADDITIONS ON α,β‐UNSATURATED KETONUCLEOSIDES: PREPARATION OF 2‐AMINO‐2‐DEOXY‐ AND 2‐THIOHEXOPYRANOS‐4‐ULOSE NUCLEOSIDES

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