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Design and Synthesis of Glycoside Inhibitors of Glioma and Melanoma Growth

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Isabel García-Álvarez,^† Guillermo Corrales,^† Ernesto Doncel-Pérez,^‡^§ Ana Muñoz, Manuel Nieto-Sampedro,*^‡^§ and Alfonso Fernández-Mayoralas*^†

Instituto de Qumica Orgnica General, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain, Hospital Nacional de Parapljicos, SESCAM, 45071 Toledo, Spain, Instituto Cajal, CSIC, Avda. Doctor Arce 37, 28002 Madrid, Spain, and Laboratorios FAES FARMA, SA, Mximo Aguirre 14, Leioa, Vizcaya

J. Med. Chem., 2007, 50 (2), pp 364–373

DOI: 10.1021/jm0611556

Publication Date (Web): December 22, 2006

†

Instituto de Química Orgánica General, CSIC.

‡

Instituto Cajal, CSIC.

Hospital Nacional de Parapléjicos, SESCAM.

Laboratorios FAES FARMA, SA.

To whom correspondence should be addressed. A.F.-M.: phone, 34 91 562 29 00; fax, 34 91 564 48 53; e-mail, mayoralas@iqog.csic.es. M.N.-S.: phone, 34 91 585 47 20; fax, 34 91 585 47 54; e-mail, mns@cajal.csic.es

Abstract

An N-acetylglucosaminide derivative with a pentaerythritol substituent at position C-6 was previously synthesized and shown to inhibit neural tumor growth. Now, we report the preparation of a series of new synthetic compounds introducing systematic changes in the nature, polarity, and size of the sugar substituents. The antimitotic activity of the new compounds was tested on cultured rat (C6) and human (U-373) glioma lines and on a human melanoma line (A-375). The antimitotic and antitumoral activity of the new compounds on glioma cell lines increased up to 2 orders of magnitude with respect to the parent compound or was abolished, permitting a detailed structure−function analysis of the new antitumorals. One of the glycosides inhibited melanoma division with an ID₅₀ below the micromolar range.

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Published In Issue January 25, 2007
Received October 5, 2006

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Article

Design and Synthesis of Glycoside Inhibitors of Glioma and Melanoma Growth

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Recommend & Share

Related Content

Central Neural Tumor Destruction by Controlled Release of a Synthetic Glycoside Dispersed in a Biodegradable Polymeric Matrix

Carbohydrate Dependent Targeting of Cancer Cells by Bleomycin−Microbubble Conjugates

Total Synthesis of the Potent Anticancer Aglaia Metabolites (−)-Silvestrol and (−)-Episilvestrol and the Active Analogue (−)-4′-Desmethoxyepisilvestrol

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