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Expanded porphyrins: functional photoacoustic imaging agents that operate in the NIR-II region.


ABSTRACT: Photoacoustic imaging (PAI) relies on the use of contrast agents with high molar absorptivity in the NIR-I/NIR-II region. Expanded porphyrins, synthetic analogues of natural tetrapyrrolic pigments (e.g. heme and chlorophyll), constitute as potentially attractive platforms due to their NIR-II absorptivity and their ability to respond to stimuli. Here, we evaluate two expanded porphyrins, naphthorosarin (1) and octaphyrin (4), as stimuli responsive PA contrast agents for functional PAI. Both undergo proton-coupled electron transfer to produce species that absorb well in the NIR-II region. Octaphyrin (4) was successfully encapsulated into 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-poly(ethylene glycol) (DSPE-PEG2000) nanoparticles to afford OctaNPs. In combination with PAI, OctaNPs allowed changes in the acidic environment of the stomach to be visualized and cancerous versus healthy tissues to be discriminated.

SUBMITTER: Chen J 

PROVIDER: S-EPMC8317656 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Expanded porphyrins: functional photoacoustic imaging agents that operate in the NIR-II region.

Chen Jingqin J   Sedgwick Adam C AC   Sen Sajal S   Ren Yaguang Y   Sun Qinchao Q   Chau Calvin C   Arambula Jonathan F JF   Sarma Tridib T   Song Liang L   Sessler Jonathan L JL   Liu Chengbo C  

Chemical science 20210623 29


Photoacoustic imaging (PAI) relies on the use of contrast agents with high molar absorptivity in the NIR-I/NIR-II region. Expanded porphyrins, synthetic analogues of natural tetrapyrrolic pigments (<i>e.g.</i> heme and chlorophyll), constitute as potentially attractive platforms due to their NIR-II absorptivity and their ability to respond to stimuli. Here, we evaluate two expanded porphyrins, naphthorosarin (<b>1</b>) and octaphyrin (<b>4</b>), as stimuli responsive PA contrast agents for funct  ...[more]

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