Supramolecular photochemistry of drugs in biomolecular environments

Abstract

In this tutorial review we illustrate how the interaction of photoactive drugs/potential drugs with proteins or DNA in supramolecular complexes can determine the course of the reactions initiated by the drug absorbed photons, evidencing the mechanistic differences with respect to the solution conditions. We focus on photoprocesses, independent of oxygen, that lead to chemical modification of the biomolecules, with formation of new covalent bonds or cleavage of existing bonds. Representative systems are mainly selected from the literature of the last decade. The photoreactivity of some aryl propionic acids, (fluoro)quinolones, furocoumarins, metal coordination complexes, quinine-like compounds, naphthaleneimides and pyrenyl-peptides with proteins or DNA is discussed. The use of light for biomolecule photomodification, historically relevant to biological photosensitization processes and some forms of photochemotherapy, is nowadays becoming more and more important in the development of innovative methods in nanomedicine and biotechnology.

Light‐Tunable Generation of Singlet Oxygen and Nitric Oxide with a Bichromophoric Molecular Hybrid: a Bimodal Approach to Killing Cancer Cells

“…This sort of lifetimei ncreaseo ccurs quite commonly upon incorporation of chromophores into biological mediao rp rotein hosts, and is usually causedb yt he protection exertedb yt he host against external quenching impurities, or to ap erturbation of the ISC process to the ground state, or to both. [49] This spectroscopic and kinetic scenario is similar to those observed with model compound 2.H owever,i nt his case it was observedt hat the relative efficiency of population of the triplets tate (F T )w as~30 % lower than that of 1 (see Experimental Section). This finding explainst he lower quantum yield of 1 O 2 observed for model Table 1.…”

Photochemical behavior of biosupramolecular assemblies of photosensitizers, cucurbit[n]urils and albumins

“…6,11,[23][24][25] Additionally, albumins can penetrate the defective vascularity of tumors and be retained. 6 In spite of these advantages, when it comes to photoactive drugs, albumins modify the photochemistry of the drugs, 30,31 and often reduce the action of photosensitizers. [32][33][34][35] Moreover, there is no general strategy to release drugs from albumins.…”

A photochemical and theoretical study of the triplet reactivity of furano- and pyrano-1,4-naphthoquionones towards tyrosine and tryptophan derivatives

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