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Nitric‐Oxide‐Releasing aza‐BODIPY: A New Near‐Infrared J‐Aggregate with Multiple Antibacterial Modalities

Xinyao Bao, Shaoqiu Zheng, Lei Zhang, Aizong Shen, Guoying Zhang, Shiyong Liu, Jinming Hu

2022Angewandte Chemie15 citationsDOI

Abstract

Abstract The development of near‐infrared (NIR) J‐aggregates has received increasing attention due to their broad applications. Here, we report the nitrosation of an amine‐containing aza‐BODIPY precursor ( BDP‐NH 2 ), affording the first nitric oxide (NO)‐releasing NIR J‐aggregate ( BDP‐NO ). The introduction of N ‐nitrosamine moieties efficiently inhibits the aromatic interactions of BDP‐NH 2 , which instead promotes the formation of J‐aggregates within micellar nanoparticles with a remarkable bathochromic shift of ≈109 nm to the NIR window (820 nm). Interestingly, the NO release and photothermal conversion efficiency (PTCE) can be delicately tuned by the loading contents of BDP‐NO within micellar nanoparticles, thereby enabling multiple antibacterial modalities by exploring either NO release, photothermal therapy (PTT), or both. We demonstrate the combination of NO and PTT can elevate antibacterial activity while attenuating PTT‐associated inflammation for the in vivo treatment of MRSA infection.

Topics & Concepts

Photothermal therapyBathochromic shiftChemistryMicelleBODIPYNitric oxidePhotochemistryCombinatorial chemistryAmine gas treatingNitrosationIn vivoNanotechnologyOrganic chemistryMaterials scienceFluorescenceAqueous solutionBiologyQuantum mechanicsPhysicsBiotechnologyNanoplatforms for cancer theranosticsPerovskite Materials and ApplicationsLuminescence and Fluorescent Materials