Curcumin and Cyclocurcumin-based Derivatives as Potential Candidates for Photocontrolled Treatment

Resumen

Cyclocurcumin is a natural compound extracted from turmeric and showing an interestingsolvent-dependent photoswitching ability. The solvent-dependent photochemistry ofcyclocurcumin has been rationalized on the basis of a competition between π-π* and n-π*states.1 Furthermore, we have reported the synthesis of a biomimetic analogue showingenhanced photochemical properties and in particular presenting photoswitching capacity invarious media.2 In addition, molecular modeling and simulation, including density functionaland wavefunction based methods were used to explore the excited states potential energysurface landscape. We realize that with cyclocurcumin, the addition of a carbon-carbondouble bond to the core of the natural compound favors the population of the π-π* state,whatever the choice of the solvent, and hence leads to photoisomerization, with fluorescencereduced to only a minor channel comparing with natural derivative.3 In addition, the two-photon absorption (TPA) cross section is also strongly increased compared to the parentcompound, paving the way to the use in biologically oriented applications. Apart of that, weare also interested in the interaction between these systems and lipidic membranes as apotential photocontrolled way to destabilize it, which can yield in cellular apoptosis or vesicledrug delivery. Likewise, natural curcumin was studied as a potential photodynamic therapycandidate taking advantage of it larger TPA comparing with other used drugs.