Chemiluminescent PEG‐PCL micelles for imaging hydrogen peroxide

Abstract

Hydrogen peroxide is one of the fundamental molecules of biology, regulating key cell signaling pathways and the development of numerous inflammatory diseases. There is therefore great interest in developing contrast agents that can detect hydrogen peroxide in vitro and in vivo. In this report, we present a new contrast agent for imaging hydrogen peroxide, termed the chemiluminescent poly(ethylene glycol)-b-poly(e-caprolactone) (PEGPCL) micelles (CPMs), which can detect hydrogen peroxide at nanomolar concentrations and chemiluminesce in the near IR range (676 nm) in the presence of hydrogen peroxide. The CPMs are composed of a PEG-PCL scaffold and have fluorescent dyes and peroxalate esters in their hydrophobic PCL core. The CPMs image hydrogen peroxide by undergoing a three-component chemiluminescent reaction involving a peroxalate ester, a fluorescent dye, and hydrogen peroxide. The CPMs also have a stealth PEG corona to enhance their circulation half life. The CPMs should find numerous applications for imaging hydrogen peroxide because of their nanomolar sensitivity, small size, and stealth pegylated surface.

Reduction of oxidative stress by p-hydroxybenzyl alcohol-containing biodegradable polyoxalate nanoparticulate antioxidant

“…In this study, the molar ratio of cyclohexanedimethanol to HBA was decided after the careful consideration of stability in aqueous environments and reactivity to H 2 O 2 [6,16]. It has been reported that the aromatic peroxalate compounds instantaneously react with H 2 O 2 specifically to decompose into carbon dioxide, and rapidly degrade under aqueous conditions via hydrolysis [6,23,24]. In contrast, polyoxalate with aliphatic peroxalate ester has low reactivity to H 2 O 2 and undergo slow hydrolytic degradation under aqueous conditions.…”

Chemiluminescent Nanomicelles for Imaging Hydrogen Peroxide and Self‐Therapy in Photodynamic Therapy

“…However, a major barrier to POCL-based systems application is that peroxalate derivatives are not so stable and inclined to hydrolyze in aqueous or protic solvents [15]. Therefore, the protection of peroxalate esters from hydrolysis is the key factor to peroxalate NPs, for example, the formation of minisize organic reactor in aqueous systems through copolymer micelles [16] or microemulsions [17]. Meanwhile, with the peroxalate esters and the fluorescent dyes together in the same phase, the energy transfer is expected to be improved [18].…”

Detection of Hydrogen Peroxide in vitro and in vivo Using Peroxalate Chemiluminescent Micelles

“…Previously, Dasari et al developed chemiluminescent micelles composed of polycaprolactone-co-polyethylene glycol (PCL-PEG) copolymer and diphenyl peroxalate which is more stable than bis(2,4,6-trichlorphenyl) oxalate in water. 16 Diphenyl peroxalate was encapsulated in the hydrophobic cores and thus protected from water hydrolysis. Diphenyl peroxalate has poor stability against water hydrolysis, but the encapsulation in the hydrophobic core of micelles increased its stability.…”