Photoactivable heterocyclic cages in a comparative release study of butyric acid as a model drug

Abstract

Aiming: at the improvement of the photorelease of butyric acid - a model carboxylic acid drug, a set of heteroaromatic compounds based on acridine, naphtho[2,1-b]pyran, 3H-benzopyran fused julolidine and thioxo-naphtho[2,1-b]pyran were evaluated as benzyl-type phototriggers, in comparison with the well-known o-nitrobenzyl group. The corresponding ester cages were irradiated in a photochemical reactor at 254, 300, 350 and 419 nm, in two solvent systems (methanol or acetonitrile in 80:20 mixtures with HEPES buffer). Photolysis studies showed that, for some of the cages, the release of the active molecule occurred with short irradiation times using 419 nm. Time-resolved fluorescence was used to elucidate their photophysical properties and determine the decay kinetics. Studies were also carried out to assess the suitability of using two-photon excitation to address these compounds, which is advantageous if their use in biological systems is to be considered

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

“…The (acridin-9-yl)methyl group ( 86 ) was introduced by Zhang and co-workers as a UV-activatable (λ max abs ≈ 355 nm, ε 360 ≈ 1 × 10 4 M –1 cm –1 ) PPG for alcohols 538 and was later used with carboxylic acids. 335 , 517 , 539 , 540 Its tail absorption in the visible range enabled photolysis at λ irr = 419 nm, albeit with low quantum efficiency (Φ r = 0.5–1.6 × 10 –4 ). 335 , 540 The photoreaction was proposed to proceed through an ion-pair intermediate.…”

S,S‐Chiral Linker Induced U Shape with a Syn‐facial Sensitizer and Photocleavable Ethene Group

“…Photoreleased molecules are of considerable interest not only in the field of photochemistry but also in site‐specific delivery applications . Current literature on sensitizer and drug photorelease has mainly focused on the use of direct UV, visible and near‐IR light to activate the release mechanisms.…”

Photoactivatable prodrugs of butyric acid based on new coumarin fused oxazole heterocycles

“…Our research has been involved in studies related with the design, synthesis and evaluation of lightsensitive moieties for the release of bioactive molecules, including butyric acid [1,2,[15][16][17][18][19][20].…”

“…Recently, we have reported on coumarin, benzocoumarin thio(benzo)coumarin, coumarin fused with julolidine and amino-substituted benzocoumarin cages [19][20][21]. Also, our studies with photoactive prodrugs of butyric acid were initiated with the use of naphthoxazoles and coumarin fused oxazoles; namely naphtho [2,3-d] [22].…”