ASSESSING THE PHARMACOLOGICAL POTENTIAL OF SYNTHETIC COLORANTS WITH PYRIDONE CORE

Azo dyes are known as structurally diverse class of organic compounds bearing one or more azo groups (–N=N–) as a bridge between organic residues of which at least one is an aromatic moiety. This group of synthetic dyes is obtained easily by the reaction of diazo coupling with high yield. The importance of azo dyes is reflected in the fact that they account for 60 % of the total number of the dye structures known to be manufactured and used in the coloration of textiles, leather, plastics and cosmetics. Aside from their traditional usage, azo dyes are known for their therapeutic properties and wide range of applications in biomedicine and pharmaceutical industry. Hereby, the present study aims to investigate the relationship between the chemical structure and pharmacological activity of four azo pyridone dyes taking into account the tautomeric form of dyes. The relationship was determined empirically using appropriate software packages as well as in vitro using the 2, 2’-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) method. The results of in silico prediction suggested that all investigated compounds possess good oral bioavailability, while the results of the ABTS assay indicate poor to excellent antioxidant activity depending on the substituent in the phenyl ring. Considering the broad applications of arylazo pyridone dyes, as well as the fact that their relative importance may increase in the future, results obtained in this study serve as a basis for further investigations.
Azo boje predstavljaju strukturno najraznovrsniju klasu organskih jedinjenja koja sadrže jednu ili više azo grupa (–N=N–) koje premošćavaju dva organska motiva od kojih je bar jedan aromatičan. Ova grupa sintetskih boja dobija se jednostavnom sintezom koja uključuje reakciju diazo-kuplovanja u visokom prinosu. Da su azo boje od neprocenjivog značaja u različitim granama industrije gde se primenjuju za nijansiranje tekstila, kože, plastike i kozmetičkih proizvoda, govori i činjenica da su zastupljene sa preko 60%. Pored tradicionalne primene, azo boje su poznate i po sve većoj upotrebu u biomedicini i farmaceutskoj industriji. Na osnovu navedeneg, cilj ovog rada je da se detaljnije ispita veza između hemijske strukture četiri azo piridonske boje i njihove farmakološke aktivnosti uzimajući u obzir tautomerni oblik boje. Ova veza određena je empirijski korišćenjem odgovarajućih softverskih paketa kao i in vitro određivanjem njihove antioksidativne aktivnosti primenom ABTS metode. Rezultati in silico predikcije pokazuju da sva ispitivana jedinjenja poseduju dobru oralnu bioraspoloživost i nisku do odličnu antioksidativnu aktivnost u zavisnosti od spupsptituenta u fenilnom jezgru. Uzimajući u obzir širok spektar primene arilazo piridonskih boja kao i činjenicu da će njihov značaj konstantno rasti, rezultati ostvareni u ovom radu predstavljaju interesantnu osnovu za buduća istraživanja.