Characterization, DNA Binding and Cleavage Activities of New Prodigiosin and Tambjamine Analogues and Their Cu²⁺ and Zn²⁺ Complexes

Abstract

Prodigiosins and tambjamines are natural compounds from bacterial and marine sources belonging to a family containing a common 4-methoxy-2,2'-bipyrrole core.These compounds have received a lot of interest due to their promising biological activities. Studies have suggested DNA as a potential therapeutic target for the natural prodigiosin and tambjamine due to their ability to facilitate oxidative DNA cleavage in the presence of Cu 2+ . Based on this we sought to study the metal binding activity of new prodigiosin and tambjamine analogues. A new prodigiosin analogue was synthesized and complexed with Cu 2+ . This revealed 1:1 complex formation between the tripyrrole and Cu 2+ that was confirmed by mass spectra and NMR spectra analysis. In addition in situ studies also revealed that our new analogues of prodigiosin cannot bind Zn 2+ when the methoxy group on ring B is replaced by an alkyl group or when one of the ring nitrogens is methylated.Our UV-Vis experiments with calf thymus DNA showed that prodigiosins and tambjamines bind DNA mainly through an external mode, suggesting that hydrogen bonding between the pyrrole ring nitrogens and the bases of DNA takes precedence over stacking interactions. For the new Cu 2+ complex synthesized however, we observed spectral changes that suggest intercalation into DNA.DNA cleavage experiments revealed that the prodigiosin-Cu complex is able to convert supercoiled DNA into its linear form. The data from the gel shift assays fit well to a first-order consecutive reaction model. In addition to preformed metal complexes, we showed DNA cleavage by in situ complexation of the ligands in the

Assessment of Binding Interaction to Salmon Sperm DNA of Two Antiviral Agents and Ecofriendly Nanoparticles: Comprehensive Spectroscopic Study

“…DNA) is attributed to light induction in chromophores resulting in dipoles interactions [50] [51]. Hyperchromicity is considered one of the important evaluators for the strength of DNA binding interaction, it represents the effect of ligand binding on DNA molecule compaction as a result of electrostatic interaction [52]. The hyperchromicity percentage was calculated according to the following equation [53] [54]: / × 100 (5) where, ε f , ε b correspond to the extinction coe cients of the free and bound forms of the complex.…”