Structural characterization and cytotoxicity studies of different forms of a combretastatin A4 analogue
| Autor: | Amanda Laura Ibiapino, Tiago Rodrigues, Laysa Pires de Figueiredo, Daniel N. do Amaral, Eliezer J. Barreiro, Fabio Furlan Ferreira, Letícia S. Ferraz, Lídia Moreira Lima |
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| Rok vydání: | 2017 |
| Předmět: |
Combretum caffrum
biology Stereochemistry Angiogenesis Melanoma Organic Chemistry 010402 general chemistry 010403 inorganic & nuclear chemistry biology.organism_classification medicine.disease 01 natural sciences 0104 chemical sciences Analytical Chemistry Inorganic Chemistry chemistry.chemical_compound chemistry Anhydrous medicine Viability assay Cytotoxicity Spectroscopy Powder diffraction Derivative (chemistry) |
| Zdroj: | Journal of Molecular Structure. 1147:226-234 |
| ISSN: | 0022-2860 |
| DOI: | 10.1016/j.molstruc.2017.06.093 |
| Popis: | It is well known that combretastatin A4 (CA-4), which is a natural stilbene isolated from Combretum caffrum, is used to inhibit angiogenesis. However, depending on the dose administered to the patient, it can cause some side-effects. Herein, we present the synthesis and structural characterization of a novel N-acylhydrazone derivative – LASSBio-1735 – a CA-4 analogue. LASSBio-1735 has displayed in vitro antiproliferative activity against HL-60 (human leukemia), SF-295 (human glioblastoma), MDA-MB435 (melanoma) and HCT-8 (ileocecal adenocarcinoma) tumor cells. We found different hydration levels in two batches of the as-synthesized compound. As a consequence, we could successfully determine the crystal structures – by using X-ray powder diffraction data and a simulated annealing procedure – of the anhydrous and hydrated forms. The effects on cell viability of anhydrous and hydrated forms of LASSBio-1735 were comparatively evaluated in different tumor cell lines, and the hydrated form exhibited higher cytotoxicity in human leukemia K562 cells. These findings lead us to perform a quantitative phase analysis on one of the samples and may shed some light on the search for possible new solvates and/or hydrates. |
| Databáze: | OpenAIRE |
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