Supramolecular Assembly Based on Sulfato-β-cyclodextrin for Hypoxia Cell Imaging

Abstract

Constructing hypoxia fluorescence probes is a developing research field, due to the hypoxic nature of many diseases, caused by an inadequate supply of oxygen. Herein, we reported a noncovalent hypoxia-responsive turn-on fluorescence probe, constructed by biocompatible sulfato-β-cyclodextrin (SCD), azobenzene derivative (1), and fluorochrome rhodamine 123 (Rho123). TEM image and dynamic light scattering (DLS) indicated that negatively multicharged SCD and positively charged 1 aggregated into nanoparticles with an average diameter of 53.8 nm through electrostatic interactions. The critical aggregation concentration (CAC) of 1 in the presence of SCD was obtained as 0.028 mM investigated by optical transmittance experiments quantitatively. The supramolecular assembly (SCD/1) works as both carrier and fluorescent quencher of Rho123. Verified by UV/vis absorption experiments, the azobenzene derivative 1 can be reduced efficiently by chemical reductant with a rate constant of 1.598 min–1. Florescence experiments showed that SCD/1 made a thoroughly quenching of Rho123 and 8-fold recovery of fluorescence intensity after reduced. Under hypoxia condition the azobenzene group of 1 was reduced by azo reductase, accompanying with the release and fluorescence recovery of Rho123. The noncovalent hypoxia-responsive ternary supramolecular assembly was used for hypoxia cell imaging.

Recent advances in the design of afterglow materials: mechanisms, structural regulation strategies and applications

“…Recently, supramolecular assembly strategies have been applied to exploit phosphorescent materials in aqueous solutions, with the approach relying on the fact that strong host-guest interactions can protect T 1 from quenchers and inhibit molecular motion in aqueous solutions. Supramolecular assembly strategies typically utilize water-soluble matrices such as CD 395,396 or CB. 397,398 As early as 1982, phosphorescence emission in the aqueous phase was realized based on CD (CD-RTP).…”

Recent Development of Supramolecular Cancer Theranostics Based on Cyclodextrins: A Review

“…Moreover, imaging time and excretion behavior can be optimized with tunable cavity sizes of CD [51][52][53][54]. Liu et al designed a hypoxia fluorescence probe composed of sulfato-β-CD, azobenzene derivative and green-fluorescent dye, which selfassembled by electronic interaction and hydrophobic interaction [55]. The system turns…”

“…Moreover, imaging time and excretion behavior can be optimized with tunable cavity sizes of CD [51][52][53][54]. Liu et al designed a hypoxia fluorescence probe composed of sulfato-β-CD, azobenzene derivative and green-fluorescent dye, which selfassembled by electronic interaction and hydrophobic interaction [55]. The system turns "off" by the supramolecular assembly skeleton to quench the fluorescence with the photoinduced electron transfer (PET) mechanism; the system turns "on" by fracture of the nitrogen-nitrogen double bond of the hypoxic-responsive azobenzene group through a reduction reaction to restore the fluorescence; hypoxic cell imaging was achieved by these fluorescence changes.…”

Noncovalent Bridged Bis(Coumarin‐24‐Crown‐8) Phosphorescent Supramolecular Switch

“…Supramolecular photoluminescence switch [ 1 ] was a current research hotspot, due to their wide applications in optoelectronic devices, [ 2 ] information encryption, [ 3 ] bioimaging, [ 4 ] and so on. [ 5 ] In the research progress of supramolecular photo‐switches, diarylethene derivatives and crown ethers were usually used as important building elements to constructed supramolecular assembly.…”