Controlling Supramolecular Structures of Drugs by Light

Abstract

Controlling physicochemical properties of lightunresponsive drugs -by light, prima facie, a paradox approach. We expanded light control by ion-pairing light-unresponsive salicylate or Ibuprofen to photo-switchable azobenzene counterions thereby reversibly controlling supramolecular structures, hence the drugs' physicochemical and kinetic properties. The resulting ion-pairs photo-liquefied into room temperature ionic liquids under ultraviolet light. Aqueous solutions showed trans-cis dependent supramolecular structures under light with wormlike aggregates decomposing into small micelles and vice-versa. Light control allowed for permeation through membranes of cis-Ibuprofen ion pairs within 12 hours in contrast to the trans ion pairs requiring 72 hours. In conclusion, azobenzene ion-pairing expands light-control of physicochemical and kinetic properties to otherwise light-unresponsive drugs.

Leveraging bile solubilization of poorly water-soluble drugs by rational polymer selection

“…Long-lasting supersaturating systems and/or strategies increasing dissolution rates address pharmaceutical challenges of poorly water-soluble drugs (PWSD) [1], including salt design [2][3][4][5][6][7], nanoparticles [8,9] and, amorphous solid dispersions (ASD) [10,11] among other approaches [12][13][14][15][16][17] to obtain reproducible and adequate pharmacokinetics (PK). Polymer excipients used for drug formulation were traditionally referred to as "inert" [18][19][20] in spite of a role in e.g.…”

Electrospun PVP-Core/PHBV-Shell Fibers to Eliminate Tailing Off for an Improved Sustained Release of Curcumin

“…Sustained release refers to the continuous supply of drugs to the human body and is important for drug delivery systems. Unlike rapid or delayed release, sustained release provides a stable release rate to ensure a safe and stable drug concentration in the blood. − Sustained release systems have aroused great interests due to their good treatment efficiency by providing a constant delivery rate of drugs; moreover, these systems can achieve “few adverse reactions and one-time administration”. − …”

Azobenzene derivatives with activity against drug‐resistant Candida albicans and Candida auris

“…[24] Among others, antimicrobial substances were synthesized in which this azobenzene core was modified only by alkyl chains (Figure 1b) as well as amphiphilic cationic azobenzene derivatives (Figure 1c). [17][18][19][20] Three cationic amphiphilic azobenzene bromide salts (5a-c), which have already been investigated as photoliquefiable ionic crystals, [21,22] and two structurally similar compounds (5d,e) were synthesized and tested for their activity against different C. albicans and C. auris strains (Scheme 1). A phenyl ring was modified with a hydrophobic alkyloxy chain before the basic azobenzene structure was synthesized.…”

“…[19,20] This contribution is in light of these serious threats. Therefore, five cationic amphiphilic azobenzene bromide salts were synthesized according to syntheses known from the literature [21,22] and their activity was tested against C. albicans and C. auris, including fluconazole-resistant strains. Furthermore, their cytotoxicity and MIC values were determined, respectively.…”