Molecular mechanisms of photosensitization XIII: a combined differential scanning calorimetry and DNA photosensitization study in non steroidal antiinflammatory drugs-DNA interaction.
A combined differential scanning calorimetry (DSC) and photosensitization study has been carried out on the interaction of several NSAID on DNA, both from calf thymus and pBR 322 plasmid. The investigated compounds were both non-steroidal anti-inflammatory drugs as well as compounds related to NSAIDs for structural similar properties, to find evidence for their ability to interact with DNA as a function of steric hindrance and polarity of the chemical structures. The considered NSAIDs were diflunisal (DFN, a salicylic derivative), naproxen (NAP), ketoprofen (KPF), suprofen (SPF) and tiaprofenic acid (TIA, arylpropionic acids). The structural criterion used was related to three different aromatic groups, biphenyl, naphthalene and benzophenone (BZP). In fact drug-DNA interaction can be revealed by variations of the enthalpies and temperatures of unfolding of DNA obtained by comparison of calorimetric peaks, where a decrease of the enthalpy is associated with the drug-DNA interaction, by engaging electrostatic bonds. Testing their ability in inducing DNA cleavage when UVA irradiated can evidence the photosensitizing properties of the drug. A good correlation was found between calorimetric and photosensitization studies. From the results obtained it can be reasonably supposed that the photocleavage depends only on the drug molecules bound to DNA.
Castelli
F
F
Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 8, 95125, Catania, Italy. fcastelli@dipchi.uncit.it
De Guidi
G
G
Giuffrida
S
S
Miano
P
P
Sortino
S
S
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry*; D001577:Benzophenones / Q000737:chemistry; D002152:Calorimetry, Differential Scanning; D002417:Cattle; D004247:DNA / Q000737:chemistry*; D004249:DNA Damage; D004269:DNA, Bacterial / Q000737:chemistry; D004278:DNA, Superhelical / Q000737:chemistry; D009690:Nucleic Acid Conformation; D010777:Photochemistry; D017319:Photosensitizing Agents / Q000737:chemistry*; D011422:Propionates / Q000737:chemistry; D013816:Thermodynamics; D014466:Ultraviolet Rays
D000894:Anti-Inflammatory Agents, Non-Steroidal; D001577:Benzophenones; D004269:DNA, Bacterial; D004278:DNA, Superhelical; D017319:Photosensitizing Agents; D011422:Propionates; C021270:tiaprofenic acid; C047723:benzophenone; D004247:DNA