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Indole-based analogs of melatonin: in vitro antioxidant and cytoprotective activities (2004)

Mor, Marco ; Silva, Claudia ; Vacondio, Federica ; [et al.]

Oxford, UK : Munksgaard International Publishers

Journal of pineal research 36 (2004), S. 0

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ISSN: 1600-079X

Source: Blackwell Publishing Journal Backfiles 1879-2005

Topics: Medicine

Notes: Abstract: The known neuroprotective actions of melatonin could be due to its antioxidant or radical scavenging activity, or they could be due to specific interactions of the indole with its receptors. A study of structure–activity relationships may provide useful information when a validated macromolecular target has not been (or is not) identified. A set of indole derivatives, with changes in the 5-methoxy and acylamino groups, the side chain position and the lipophilic/hydrophilic balance, were selected and tested for their in vitro antioxidant potency in the ABTS (2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid disodium salt) and thiobarbituric acid reactive substances (TBARS) assays and for their cytoprotective activity against kainate excitotoxicity on cerebellar cell cultures. No quantitative model was able to relate the potencies obtained in the two antioxidant assays, probably because they are related to different physico-chemical properties. However, the lipophilicity of the compounds and the antioxidant potency in the TBARS assay were linearly correlated. This may be due to improved access to the lipidic substrate, where the antioxidant action occurs. In the cytoprotection assay, most compounds showed potencies comparable with or lower than melatonin. An exception was N-[2-(5-methoxy-1H-indol-2-yl)ethyl]acetamide (12), yielding, at 50 μm, percentages of cell vitality higher than 75%, while melatonin EC50 was 333 μm. No correlation was observed between cytoprotective and antioxidant potencies, nor with MT1 or MT2 receptor affinity. Compound 12 is a low-affinity antagonist at melatonin membrane receptors, and one of the most potent compounds in the antioxidant assays; its cytoprotective potency and the absence of agonist activity at melatonin membrane receptors make it a valid candidate for further investigations.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1046/j.1600-079X.2003.00102.x

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Electron impact ionization and fast atom bombardment mass spectrometry of some 3,3-dimethyl-1-(isoxazol-3-yl)triazenes, a new class of potential anticancer agents (1995)

Orsatti, Laura ; Seraglia, Roberta ; Traldi, Pietro ; [et al.]

Chichester : Wiley-Blackwell

Biological Mass Spectrometry 30 (1995), S. 1567-1573

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ISSN: 1076-5174

Keywords: Chemistry ; Analytical Chemistry and Spectroscopy

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology , Physics

Notes: A series of 3,3-dimethyl-1-(isoxazol-3-yl)triazenes, potential anticancer agents, were studied by electron impact (EI) ionization and fast atom bombardment mass spectrometry. Their behaviour was compared with that of dacarbazine, 5-(3,3-dimethyl-1-triazenyl)-(1H)-imidazole-4-carboxamide, which is employed in the treatment of several neoplastic conditions. An interesting EI-generated decomposition pathway was observed, consisting in the primary formation of [NH2CH3]+ cations, involved in the metabolic pathway of triazenes, as the alkylating agent responsible for the anticancer properties of the drug. A higher thermodynamic stability of the examined compounds than decarbazine was observed, which reasonably reflects the higher chemical stability.

Additional Material: 3 Ill.