Phenolic esters with potential anticancer activity - the structural variable

Machado, Nelson; Calheiros, Rita; Fiuza, Sónia M.; Borges, Fernanda; Gaspar, Alexandra; Garrido, Jorge; Marques, M. P. M.

doi:10.1007/s00894-007-0174-y

Cited by 21 publications

(23 citation statements)

References 32 publications

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“…The present results are in perfect agreement with the ones obtained for cinnamic acid [43] and its analogues, such as hydroxycinnamic acid and its ester or amide derivatives [44][45][46][47][48][49]. In particular, the conformational preferences of naturally occurring hydroxycinnamic acids differing in the ring substitution pattern is strongly dependent on the number, type and relative orientation of these substituents (hydroxyl and/or methoxyl groups).…”

Section: Discussionsupporting

confidence: 90%

“…However, both geometries should be taken into consideration for structural, chemical and biological studies regarding hydroxycinnamic acids since they are the most populated ones at room temperature. In di-and tri substituted compounds a stabilising intramolecular H-bond is formed, which is known to be energetically favourable in this kind of phenolic systems [44][45][46][47][48][49]57], and is therefore essential for the interpretation of their structure-activity relationships (SAR's).…”

Section: Discussionmentioning

confidence: 99%

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Conformational behaviour of biologically active ferulic acid derivatives

Calheiros¹,

Borges²,

Marques³

2009

Journal of Molecular Structure: THEOCHEM

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a b s t r a c tThe conformational behaviour of several biologically relevant hydroxycinnamic systems -ferulic acid and its methyl, ethyl, propyl and butyl esters -was studied by quantum mechanical calculations, at the DFT level. A full geometry optimisation was carried out, as well as a Fourier analysis of the main internal rotations within these molecules. The geometrical preferences of these compounds result from a balance between the stabilising resonance and hydrogen bonding effects and the destabilising non-bonding repulsions, the most stable conformers displaying an s-cis conformation and hydroxyl/methoxyl substituent groups coplanar to the aromatic ring. The results thus obtained allow a better understanding of the well recognised in vitro and in vivo antioxidant and growth-inhibiting properties of this type of phenolic systems.

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Section: Discussionsupporting

confidence: 90%

Section: Discussionmentioning

confidence: 99%

Conformational behaviour of biologically active ferulic acid derivatives

Calheiros¹,

Borges²,

Marques³

2009

Journal of Molecular Structure: THEOCHEM

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“…For all the caffeates under study, a new band was detected in the solutions at about 1700 cm −1 , as compared to the spectra of the solid compounds [16] (Tables 1, and 2, and Tables S1 and S2, in Supporting Information). This is ascribed to the C O stretching vibration of the monomer, not involved in intermolecular Hbonding, which explains the expected shift to high wavenumbers (calculated value ca 1720 cm −1 [16,20] ) relative to the ν C O of the H-bonded carbonyl in the dimeric species (ca 1660-1680 cm −1 in the solid. [16] ) Actually, while the dimeric species is expected to be largely predominant in the solid, dilution is responsible for the presence of an increasing monomer population, giving rise to Raman bands due to the free carbonyl group (not implicated in intermolecular H-bonds).…”

Section: Dft Calculationsmentioning

confidence: 82%

Antioxidant phenolic esters with potential anticancer activity: solution equilibria studied by Raman spectroscopy

Machado

Calheiros

Gaspar

et al. 2008

J Raman Spectroscopy

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The solution Raman pattern of a series of structurally related hydroxycinnamic and hydroxybenzoicesters (caffeates and gallates) with potential antioxidant/anticancer activity was studied, for different biologically significant concentrations. The spectra were assigned with the help of theoretical calculations in the light of previously reported experimental data for these compounds in the solid state. Evidence of the formation of dimeric entities in solution, via (C) O· · ·H(O) and/or (C) O· · ·H(C) intermolecular hydrogen bonds, was obtained. The dimer-to-monomer equilibrium, which influences the antioxidant activity of this kind of systems, was monitored through Raman titration experiments.

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“…pH, temperature, ionic strength or exposure to drugs). 22,27,28 Following previous studies by the authors on dietary polyphenolic compounds -both regarding their structural and conformational preferences 17,[29][30][31][32][33][34][35][36][37][38][39][40] and their chemopreventive and/or chemotherapeutic properties towards several cancer cells -the present work reports the effect of daidzein on the biochemical profile of two human breast cancer cell lines: MCF-7 (estrogendependent, ER + ) and MDA-MB-231 (estrogen-independent, ER -). The results thus obtained are expected to help establishing an accurate balance between DAID´s antioxidant and prooxidant capacities, aiming at a prospective use against breast cancer: either as a chemopreventive agent (sole or in combination with other flavones) or as an adjuvant in chemotherapy (coupled with conventional drugs such as tamoxifen, paclitaxel, docetaxel, methotrexate, gemcitabine or doxorubicin 41,42 and cisplatin.…”

Section: A Introductionmentioning

confidence: 99%

Raman microspectroscopy for probing the impact of a dietary antioxidant on human breast cancer cells

et al. 2016

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Breast cancer is the second most common type of cancer worldwide and the most frequent among women, being the fifth cause of death from neoplastic disease. Since this is an oxidative-stress related neoplasia, it is largely preventable. A dietary isoflavone abundant in soybean -daidzein -was currently investigated as to its chemopreventive and/or chemotherapeutic properties towards the human MDA-MB-231 (metastatic, estrogen-unresponsive) and MCF-7 (estrogen-responsive) breast cancer cell lines. Biological assays for evaluation of antitumour and anti-invasive activities were combined with state-of-theart vibrational microspectroscopy techniques. At 50 and 100 µM concentrations and 48 h incubation time, daidzein was found to induce a marked decrease in cell viability (ca. 50%) for MDA-MB-231 and MCF-7 cells (respectively ca. 50% and 42%) and 40% inhibition of cell migration 48 h. MicroRaman analysis of fixed cells upon exposure to this isoflavone unveiled its metabolic impact on both cell lines. Multivariate data analysis (unsupervised PCA) led to a clear discrimination between control and DAID-exposed cells, with distinctive effects on their biochemical profile, particularly regarding DNA, lipids and protein components, in a cell-dependent way. This is the first reported study on the impact of dietary antioxidants on cancer cells by microRaman techniques. A IntroductionCancer is one of the major causes of morbidity and mortality worldwide, closely following cardiovascular disorders. Breast carcinoma, in particular, is an important public health problem since it is the second most lethal cancer among women worldwide: according to the World Health Organisation (WHO), it affects 28% of the women in Europe 1 , being the second most lethal cancer type in Portugal (16%). 2 Epidemiological evidence has demonstrated a clear difference in breast cancer incidence between eastern and western countries, asian women being the least affected, which can be closely related to dietary habits.Phytochemicals, secondary plant metabolites widespread in fruits, vegetables, cereals and beverages such as tea, coffee and wine, and very abundant in a mediterranean diet, are an abundant source of dietary antioxidants known to significantly decrease the harmful effect of oxidative species, thus being promising chemopreventive agents towards carcinogenesis. [3][4][5][6] Actually, several studies have established a direct relationship between the intake of polyphenols and the prevention of oxidative stress-induced diseases, namely neurodegenerative and cardiovascular disorders, and some types of cancer. 7,8 The isoflavone daidzein (DAID), in particular, is the second most abundant component of soybean (following genistein), a growingly consumed food product, which renders this isoflavone a very suitable target of study regarding its potential health beneficial effects. In addition, it exhibits structural and functional similarities to the endogenous hormone estrogen 9 (Fig. 1). Since some breast cancers are estrogen-dependent (ER + ), DAID may...

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Phenolic esters with potential anticancer activity - the structural variable

Cited by 21 publications

References 32 publications

Conformational behaviour of biologically active ferulic acid derivatives

Conformational behaviour of biologically active ferulic acid derivatives

Antioxidant phenolic esters with potential anticancer activity: solution equilibria studied by Raman spectroscopy

Raman microspectroscopy for probing the impact of a dietary antioxidant on human breast cancer cells

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