A multifunctional β-cyclodextrin-conjugate photodelivering nitric oxide with fluorescence reporting

Abstract

This contribution reports the design, synthesis and photochemical properties of a novel cationic, water soluble, β-cyclodextrin (βCD) conjugate integrating an anthracene moiety and a nitroaniline derivative A c c e p t e d M a n u s c r i p t 2 βCD derivative represents an intriguing candidate for further studies in biopharmaceutical research addressed to multimodal therapeutic applications.

Nitric Oxide Photoreleasers with Fluorescent Reporting

“…[34] The same photocage and reporter components of dyad 3 have been also covalently joined by using a functional spacer such as a positively charged β-CD scaffold to obtain compound 5 (Figure 3). [35] The close spatial proximity between the two chromogenic units allows the fluorescence of the reporter to be quenched by FRET and restored after NO photorelease. This emission turn-on was accompanied by a lengthening of the fluorescence lifetime of the reporter after the irradiation (inset, Figure 3).…”

“…In fact, it makes the molecular construct fully soluble in water medium, provides many easily abstractable H atoms indispensable for the formation of the photoproduct after NO photorelease and also offers the possibility to accommodate additional hydrophobic guests within the β-CD cavity without affecting the photochemical and photophysical performances of 5. [35] Anthracene has been also used as both phototrigger and fluorescent reporter to simulate the NO release from the dyad 6 (Figure 4). [36] SPE and TPE excitation of anthracene leads to the release of the cupferron 7, which, in turn, spontaneously liberates NO.…”

Therapeutic Delivery of Nitric Oxide Utilizing Saccharide-Based Materials

“…Molecular structures of the fluorescent monomer (a) AN-β-CD and (b) β-CD-NOPD and the phototherapeutic β-CD polymer (c) AN-β-CD-NOPD, and the fluorescent monomer (d) FITC-β-CD and (e) β-CD-NOPD photodonor; preparation of nitroso-modified β-CD, (f) mono-SNO-β-CD and (g) multi-SNO-β-CD, and N -diazeniumdiolate modified β-CD, (h) mono-NONOate-β-CD and (i) multi-NONOate-β-CD. Panels a–c reprinted with permission from ref . Copyright 2017 Elsevier.…”

Programmed Synthesis of Hepta‐Differentiated β‐Cyclodextrin: 1 out of 117655 Arrangements

“…[4,5] Tabushi and Breslow showed that by the use of bridging disulfonyl chlorides with an appropriate geometry it was possible to make disulfonate esters of b-CD with some regioselectivity [4,5] and synthesized beautiful bis-heterofunctional CDs with enzyme-like activities and some enantioselectivity. [6] However,t his line of research slowly died out, most likely due to the difficult implementation of the poly-hetero-functionalization methods.D ifficulty linked to the moderate regioselectivities and subsequent tedious chromatographic separations.A ctually, even now,although alot of applications of CDs rely on their multi-functionalization, random functionalization is commonly used [7][8][9] instead of ar egioselective method which is apparently still seen as an arduous task. It is true that due to the presence of multiple equivalent OH groups random reaction of only the 7primary hydroxyls of b-CD,constituted of 7glucose units,with 7different reagents of equal reactivity statistically leads to am ixture of 117655 different molecules, ranging from 7molecules bearing 7times the same substituent to 720 molecules with 7d ifferent substituents.…”