Ultraviolet Light- or pH-Triggered Nitric Oxide Release from a Water-Soluble Polymeric Scaffold

Abstract

To develop nitric oxide (NO)-releasing donors, we synthesized N-nitrosamine-functionalized water-soluble alternating copolymer as a macromolecular scaffold with a high half-life. A reversible addition–fragmentation chain transfer polymerization of maleic anhydride (MA) and styrene (S) using poly­(ethylene glycol) methyl ether (mPEG) containing macro-chain transfer agent (mPEG-CDP) (CDP = 4-cyano-(dodecylsulfanyl­thiocarbonyl)­sulfanyl pentanoic acid) produced the mPEG-b-P­(MA-alt-S) polymeric scaffold, which was further modified with NO binding motifs. NO detection performed by Griess assay and 1,2-diaminoanthraquinone demonstrated a controlled release of NO from the polymer in acidic pH or with 254 nm UV light.

Nitric Oxide Releasing Delivery Platforms: Design, Detection, Biomedical Applications, and Future Possibilities

“…108 Recently, we have developed N-nitrosamine-based NO donating water-soluble alternating copolymer, mPEG-b-P(MA-alt-S) (Figure 16A). 109 We prepared different varieties of aliphatic (P1NO, P2NO, and P3NO) and aromatic (P4NO) amine-conjugated NO donors by modifying the mPEG-b-P(MA-alt-S). We observed prolonged and spontaneous NO release from P4NO in acidic pH or under the exposure of UV light (254 nm) (Figure 16B,C).…”

“…They also reported that these scaffolds are toxic against human squamous carcinoma cells (A431), and the 2 mg/mL polymer solution could reduce the cell viability up to ∼40% upon 405 nm light exposure . Recently, we have developed N -nitrosamine-based NO donating water-soluble alternating copolymer, mPEG- b -P­(MA- alt -S) (Figure A) . We prepared different varieties of aliphatic (P1NO, P2NO, and P3NO) and aromatic (P4NO) amine-conjugated NO donors by modifying the mPEG- b -P­(MA- alt -S).…”

“…(C) Nitric oxide release from P4NO and M-NO under the UV light (254 nm) exposure. Reproduced with permission from ref . Copyright (2021) American Chemical Society.…”

Styrene‐Maleimide/Maleic Anhydride Alternating Copolymers: Recent Advances and Future Perspectives

“…Recently, our group has developed such polymeric NO carrier by modifying the mPEG containing S‐MA copolymer. [ 124 ] Various types of diamine compounds were introduced in the S‐MA backbone by post‐polymerization modification reactions ( Figure ). The study implied that the N ‐phenyl ethylenediamine conjugated copolymer (P4NO) exhibited a significant NO release in the presence of acidic pH or UV‐light (254 nm).…”

Nitric Oxide-Releasing Tryptophan-Based Poly(ester urea)s Electrospun Composite Nanofiber Mats with Antibacterial and Antibiofilm Activities for Infected Wound Healing

“…Nitric oxide (NO) has currently attracted widespread attention in killing planktonic bacteria and removing biofilms due to its broad-spectrum antibacterial properties. , The radical nature of NO allows it to diffuse freely across lipid membranes and interact with different macromolecules. , Hence, NO can react with EPS to destroy the integrity of the bacterial biofilm, inducing the gathered bacteria to transform into planktonic bacteria. , NO can also interact with hydrogen peroxide and superoxide free radicals in bacteria, causing the bacteria to die. − Moreover, researchers have shown that NO plays a critical role in physiological activity, such as angiogenesis, cell proliferation, collagen deposition, and wound repair . Although NO has shown excellent performance in treating infected wounds, its relatively short half-life limits its clinical application .…”