Interaction between DNA and polycyclic aromatic hydrocarbons

Liquori, A. M.; Lerma, B. De; Ascoli, Franca; Botrê, Claudio; Trasciatti, M.

doi:10.1016/s0022-2836(62)80125-9

Cited by 93 publications

(30 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We assume that the binding ratio is low enough to set CfjICN << n in Eq. (1); then we obtain K' = cfj/cFcIy (2) When combined with the Beer-Lambert law for pyrene absorbance, Eq. (2) can be rearranged to the Benesi-Hildebrand equation23…”

Section: Spectral Methodsmentioning

confidence: 99%

Physical binding of pyrene and phenanthrene to native and denatured DNA: Measurements by spectral and coupled‐column liquid chromatography methods

Nelson

DeVoe

1984

Biopolymers

View full text Add to dashboard Cite

SynopsisThe physical (noncovalent) binding of pyrene and phenanthrene to calf-thymus DNA in aqueous NaCl solutions was measured by a spectral method (analysis of absorption spectra by Henesi-Hildebrand plots) and a coupled-column liquid chromatography method (equilibration of DNA solutions with solid hydrocarbon in a generator column and analysis of dissolved hydrocarbon by liquid chromatography). The measurements yielded values of an affinity constant K' = n K , where n is the apparent number of binding sites per nucleotide and K is the apparent binding constant. The affinity of native DNA for pyrene decreases monotonically with increasing NaCl concentration, whereas the affinity of heat-denatured DNA exhibits a maximum at 0.10M NaCl. K' for the binding of phenanthrene to native DNA is an order of magnitude lower than K' for pyrene. The molar enthalpy for the binding of pyrene to native DNA in 10 mM NaCl is (-34.0 f 1 .0) kJ niol-'. The spectral method data indicate that 50 is an upper limit for the average number of base pairs between intercalation sites for pyrene along the DNA helix and that only a fraction of these sites are hound a t the highest binding ratios.

show abstract

Section: Spectral Methodsmentioning

confidence: 99%

Physical binding of pyrene and phenanthrene to native and denatured DNA: Measurements by spectral and coupled‐column liquid chromatography methods

Nelson

DeVoe

1984

Biopolymers

View full text Add to dashboard Cite

show abstract

“…A number of polycyclic aromatic hydrocarbons (PAHs) and their derivatives in view of their planar ring system are known to intercalate with DNA resulting in the anticancer activity [7,8]. PAHs have the potential to disrupt the normal function of cellular DNA and could lead to mutagenesis, carcinogenesis and even cell death [9,10]. A variety of phenanthrene ring systems intercalate with DNA, giving rise to many drugs that possess chemotherapeutic activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and potential cytotoxic activity of new phenanthrylphenol-pyrrolobenzodiazepines

Kamal

Sreekanth

Kumar

et al. 2010

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

“…There is also some contribution from scattered light for which no correction is made, so that the true extent of quenching may be rather more than the recorded levels. The individual excitation and fluorescence peaks of free benzopyrene are a t 8-10 nm shorter wavelengths than those of the DNA-bound form [1,2,18,19]. …”

Section: Methodsmentioning

confidence: 99%

“…On raising the p H there is a rapid loss of dissolved hydrocarbon. Earlier studies of the effects of partial dilutiondenaturation [2] and heat-denaturation [8] and the increased binding observed a t very low ionic strength lead to the suggestion that hydrocarbon binding is favoured in less well ordered regions of the DNA and the present result is in accordance with this idea since the p H levels where solubilization is maximal correspond to those a t which limited flexible singlestranded regions are produced in the DNA [24] and where the effects are partially reversible on raising the pH.…”

Section: Effect Of Phmentioning

confidence: 99%

Influence of pH and Metal Ions on the Fluorescence of Polycyclic Hydrocarbons in Aqueous DNA Solution

Green¹

1970

European Journal of Biochemistry

View full text Add to dashboard Cite

The fluorescence of benzo [a]pyrene or perylene solubilized in DNA solutions of low ionic strength is strongly quenched either by addition of silver ions at a ratio Ag+:DNA phosphate <0.15 or by lowering the pH from 7.5 to 5. I n poly d(A-T) solutions the effects are much less marked than in DNA. Cu2+ ions are also effective quenchers in this system and Co2+ and Ni2+ have some activity but little effect is seen with Mn2+, Zn2+, Cd2+, Mg2+ or Na+ ions.The results establish that GC pairs play the dominant role in these quenching reactions and show that the DNA bases have a specific role in the DNA/hydrocarbon interaction. They also suggest that GC-containing sites are the major sites of physicochemical fixation of hydrocarbons to DNA.No gross difference in the general nature of the DNA binding sites was found for the carcinogenic benzo[a]pyrene and non carcinogenic perylene.Although polycyclic hydrocarbons were the first pure chemical compounds shown to posses carcinogenic activity, the way in which they induce heritable malignant changes in cells remains unknown. Unlike certain other classical chemical carcinogens (e.g. aromatic amines) all the metabolic derivatives which have so far been tested are less carcinogenic than the parent hydrocarbons so that it is likely that either the hydrocarbon itself or possibly a closely related species produced early in metabolism is the proximate carcinogen.A reaction such as intercalation of a hydrocarbon molecule between the bases of DNA assumes importance as a mechanism by which a chemically inert (but relatively planar) molecule could induce an alteration in a cell's inherited information. This could be direct (as in the case of acridines) but the reaction could also be the basis for the localization of a metabolically activated species in a biologically important site. It is now well established [l-61 that physical binding of polycyclic hydrocarbons to DNA does occur, characterized by their increased solubility in aqueous DNA solution, and an interesting distinction has been observed recently The nature of the physical binding of hydrocarbons to DNA is not proved beyond doubt, mainly because the low solubility of these hydrophobic molecules in aqueous media poses formidable problems. To attain concentrations a t which spectral measurements can be made it is necessary to work a t high DNA concentrations (approx. 1 mM P ) and low ionic strength [1-31 but even here, when the solubility of benzo [a]pyrene is increased 100-fold compared with that in water alone, the levels are still only 1-2 pM. The evidence obtained so far, (the requirement for some stacked or doublestranded structure for the reaction [1,8-lo] the spectral shifts [l, 2,5] and especially the orientation of the hydrocarbon molecules more or less perpendicular to the DNA helix axis [11,12]) is consistent with intercalation between the DNA base pairs. It seemed worthwhile to try to clarify further the nature of this physical DNA-hydrocarbon interaction. One property which might be expected is that the behaviour...

show abstract

Interaction between DNA and polycyclic aromatic hydrocarbons

Cited by 93 publications

References 26 publications

Physical binding of pyrene and phenanthrene to native and denatured DNA: Measurements by spectral and coupled‐column liquid chromatography methods

Physical binding of pyrene and phenanthrene to native and denatured DNA: Measurements by spectral and coupled‐column liquid chromatography methods

Synthesis and potential cytotoxic activity of new phenanthrylphenol-pyrrolobenzodiazepines

Influence of pH and Metal Ions on the Fluorescence of Polycyclic Hydrocarbons in Aqueous DNA Solution

Contact Info

Product

Resources

About