The modulation of the DNA-damaging effect of polycyclic aromatic agents by xanthines

Kapuściński, Jan; Ardelt, Barbara; Piosik, Jacek; Zdunek, Malgorzata; Darzynkiewicz, Zbigniew

doi:10.1016/s0006-2952(01)00904-2

Cited by 31 publications

(11 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Systems falling outside of the typical range of enthalpies are those close to zero value, i.e. ΔH h = −624 J/mol for CAF-MPTP [126], presumably due to minimal overlap of aromatic moieties in the hetero-complex, and for the CAF-quinacrine mustard system with ΔH h = −486 J/mol [124], which is difficult to interpret so far.…”

Section: International Reviews In Physical Chemistry 23mentioning

confidence: 96%

“…However, the first reports about a decrease/ increase in the toxicity of antitumor aromatic drugs in the presence of caffeine (for reviews see [19,43]) appeared at the end of the 1970s and early 1980s, which stimulated investigations into the mechanism of the action of caffeine and other methylxanthines. The hetero-association with xanthines (termed the 'interceptor' action) had been first suggested as the principal factor altering the biological activity of the drugs [52,120,121] and carcinogens [122,123], which was supported later on by numerous in vitro studies [121,[124][125][126][127][128]. The search for other aromatic interceptor molecules resulted in discovering the interceptor effect of chlorophylline (CHL) [41,44] and riboflavin [vitamin B2 (RBF) or its analogue, flavin-mononucleotide (FMN)] [129][130][131].…”

Section: Hetero-association Of Aromatic Drugs With Aromatic Interceptmentioning

confidence: 99%

“…Hetero-association in Drug-xanthine systems has been extensively studied by NMR, UV-vis, Fluorescence spectroscopies, titration microcalorimetry, partitioning in waterorganic mixture, molecular modelling and other techniques for the following aromatic drugs: daunomycin (DAU) [127,[133][134][135][136], doxorubicin (DOX) [33,42,127,[137][138][139], actinomycin D (AMD) and its derivatives [133,[140][141][142][143], benzene and its derivatives [122,144], novantrone/mitoxantrone (NOV) [42, 127, 135-137, 145, 146], nogalamycin (NOG) [138], norfloxacin (NOR) [135,136,147], camptothecins [139,148,149], quinoxaline [84], chloroquine [84], DAPI [150], phenothiazines [121,151,152], riboflavin [135,[153][154][155], porphyrins [156,157], acridine mutagens [53,54,124,125,[133][134]…”

Section: Drug-xanthine Systemmentioning

confidence: 99%

“…The chromophores of the drug and xanthine in the majority of cases are oriented in a way to maximise the area of their overlap (i.e. the longitudinal axes of the chromophores of the drug and xanthine molecules tend to be parallel) [42,124,125,133,135,137,139,159], except for the cases of THP-NOV [135] and, probably, CAF-DOX [139] systems in which the longitudinal axes are nearly orthogonal (the CAF-DOX seems to be the only system for which the early [42,137] and recent [139] calculations of the structure of 1:1 hetero-complex disagree with respect to the angle of orientation of CAF to the DOX chromophore). The key difficulty in structural modelling of drug-xanthine systems is that the xanthine molecule allows at least two possible orientations differing by 180º in the complex with the drug [133,137,139], which sometimes cannot be reliably discriminated by experiment or in structural modelling.…”

Section: Drug-xanthine Systemmentioning

confidence: 99%

See 3 more Smart Citations

Hetero-association of aromatic molecules in aqueous solution

Evstigneev

2014

International Reviews in Physical Chemistry

View full text Add to dashboard Cite

Knowledge of the physical chemistry of small molecules complexation (the hetero-association) in aqueous solution is increasingly important in view of the rapidly emerging branch of supramolecular chemistry dealing with the formation of heterogeneous polymeric structures having specific functional roles. In this paper, the 50-year history of scientific studies of hetero-association of heterocyclic aromatic molecules in aqueous solution has been reviewed. Some important correlations of structural and thermodynamic parameters of complexation have been reported based on large data-set of hetero-association parameters accumulated to date. The fundamental problem of 'energetic composition' of π-stacking is extensively discussed. The review has shown that there are some gaps in our understanding of heteroassociation, which provides a challenge for further studies in this area.

show abstract

Section: International Reviews In Physical Chemistry 23mentioning

confidence: 96%

Section: Hetero-association Of Aromatic Drugs With Aromatic Interceptmentioning

confidence: 99%

Section: Drug-xanthine Systemmentioning

confidence: 99%

Section: Drug-xanthine Systemmentioning

confidence: 99%

See 2 more Smart Citations

Hetero-association of aromatic molecules in aqueous solution

Evstigneev

2014

International Reviews in Physical Chemistry

View full text Add to dashboard Cite

show abstract

“…It has been previously reported that methylxanthines are able to protect cells against the cytostatic and cytotoxic effects of some aromatic compounds by reduction of their mutagenic activity [2, 3]. Caffeine and other methylxanthines can form stacking complexes with several aromatic compounds, like anticancer drugs [2, 4], fluorescence dyes [5–9], mutagens [10, 11], neurotoxins [12, 13] and others [14, 15]. The authors of papers cited above assumed that hetero-association of methylxanthines with these compounds may diminish their biological activity.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Study of Porphyrin-Caffeine Interactions

Makarska-Białokoz

2012

J Fluoresc

View full text Add to dashboard Cite

The association between water-soluble porphyrins: 4,4′,4″,4‴-(21 H ,23 H -porphine-5,10,15,20-tetrayl)tetrakis-(benzoic acid) (H 2 TCPP), 5,10,15,20-tetrakis(4-sulfonatophenyl)-21 H ,23 H -porphine (H 2 TPPS 4 ), 5,10,15,20-tetrakis[4-(trimethylammonio)phenyl]-21 H ,23 H -porphine tetra- p -tosylate (H 2 TTMePP), 5,10,15,20-tetrakis(1-methyl-4-pyridyl)-21 H ,23 H -porphine tetra- p -tosylate (H 2 TMePyP), the Cu(II) complexes of H 2 TTMePP and H 2 TMePyP, as well as chlorophyll a with caffeine (1,3,7-trimethylxanthine) has been studied analysing their absorption and emission spectra in aqueous (or acetone in case of chlorophyll a) solution. During the titration by caffeine the porphyrins absorption spectra undergo the evolution – the bathochromic effect can be observed as well as the hypochromicity of the Soret maximum. The association constants were calculated using curve-fitting procedure (K AC of the order of magnitude of 10 3 mol -1 ). Whereas the emission spectra point at the presence of the fluorescence quenching effect testifying for the partial inactivation of the porphyrin molecule. The fluorescence quenching constants were calculated from Stern-Volmer plots. The results obtained show that caffeine can interact with water-soluble porphyrins and through formation of stacking complexes is able to quench their ability to emission.

show abstract

An insight towards anticancer potential of major coffee constituents

et al. 2018

View full text Add to dashboard Cite

Cancer is a complex disease that transforms a normal cell into a malignant cell by disturbing different molecular mechanisms. Lately, plant‐derived bioactive products have gained prominent attention to serve as anti‐cancer agents. These natural anti‐neoplastic agents are believed to act as alternatives for the synthetic drugs or could be used to enhance the prospect of other drugs in reducing their dose, thus limiting their possible toxic effects. They could also counterbalance the other anti‐cancer drug‐induced adverse effects. Among natural plant‐derived products, coffee has been reported for its significant anti‐carcinogenic effects in the scientific literature. This article aims to highlight the anti‐cancer potential of different coffee components viz. caffeic acid, chlorogenic acids, caffeine (1,3,7‐trimethylxanthine), cafestol, ferulic acid, and kahweol together in a single article. Based on our article, it is quite clear that these bioactive components have important therapeutic potentials against cancerous cells. However, the lack of clinical data negates their use in humans. Therefore, more research is recommended to achieve the desired pharmaceutical value. We also implore assessing their safety and possible adverse effects prior to their progress into clinical trials. © 2018 BioFactors, 44(4):315–326, 2018

show abstract

The modulation of the DNA-damaging effect of polycyclic aromatic agents by xanthines

Cited by 31 publications

References 28 publications

Hetero-association of aromatic molecules in aqueous solution

Hetero-association of aromatic molecules in aqueous solution

Spectroscopic Study of Porphyrin-Caffeine Interactions

An insight towards anticancer potential of major coffee constituents

Contact Info

Product

Resources

About