title: Design, synthesis, and bioactivity of putative tubulin ligands with adamantane core.
abstract: Several adamantane-based taxol mimetics were synthesized and found to be cytotoxic at micromolar concentrations and to cause tubulin aggregation. The extent of the aggregation is maximal for N-benzoyl-(2R,3S)-phenylisoseryloxyadamantane (5) and is very sensitive to the structural modifications. A hybrid compound (15), combining adamantane-based taxol mimetic with colchicine was synthesized and found to possess both microtubule depolymerizing and microtubule bundling activities in A549 human lung carcinoma cells.
authors: Department of Chemistry, M. V. Lomonosov Moscow State University, 119992 Moscow, Russian Federation. olgaz@org.chem.msu.ru
authors: Olga N
authors: ON
authors: Zefirova
authors: Evgeniya V
authors: EV
authors: Nurieva
authors: Heiko
authors: H
authors: Lemcke
authors: Andrei A
authors: AA
authors: Ivanov
authors: Dmitrii V
authors: DV
authors: Shishov
authors: Dieter G
authors: DG
authors: Weiss
authors: Sergei A
authors: SA
authors: Kuznetsov
authors: Nikolay S
authors: NS
authors: Zefirov
mesh_terms: D000218:Adamantane / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001921:Brain / Q000378:metabolism; D002417:Cattle; D003078:Colchicine / Q000494:pharmacology; D020650:Combinatorial Chemistry Techniques; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008870:Microtubules / Q000378:metabolism; D018716:Molecular Mimicry; D017239:Paclitaxel / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014404:Tubulin / Q000737:chemistry / Q000378:metabolism*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D014404:Tubulin; D017239:Paclitaxel; D000218:Adamantane; D003078:Colchicine