Controlled and Selective Photo-oxidation of Amyloid-β Fibrils by Oligomeric p-Phenylene Ethynylenes

Fanni, Adeline M.; Okoye, Daniel; Monge, Florencia A.; Hammond, Julia; Maghsoodi, Fahimeh; Martin, Tye D.; Brinkley, Gabriella; Phipps, M. Lisa; Evans, Deborah G.; Martinez, Jennifer S.; Whitten, David G.; Chi, Eva Y.

doi:10.1021/acsami.1c22869

Title: Controlled and Selective Photo-oxidation of Amyloid-β Fibrils by Oligomeric p-Phenylene Ethynylenes

Journal Article · Mon Mar 28 00:00:00 EDT 2022 · ACS Applied Materials and Interfaces

DOI:https://doi.org/10.1021/acsami.1c22869· OSTI ID:1879388

^[1]; Okoye, Daniel ^[1]; Monge, Florencia A. ^[1]; Hammond, Julia ^[2]; Maghsoodi, Fahimeh ^[1];

^[1]; Brinkley, Gabriella ^[3]; Phipps, M. Lisa ^[4];

^[1];

^[5];

^[1];

^[1]

Univ. of New Mexico, Albuquerque, NM (United States)
Univ. of New Mexico, Albuquerque, NM (United States); Rose-Hulman Inst. of Technology, Terre Haute, IN (United States)
Univ. of New Mexico, Albuquerque, NM (United States); University of Minnesota, Duluth, MN (United States)
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Northern Arizona Univ., Flagstaff, AZ (United States)

Photodynamic therapy (PDT) has been explored as a therapeutic strategy to clear toxic amyloid aggregates involved in neurodegenerative disorders such as Alzheimer’s disease. A major limitation of PDT is off-target oxidation, which can be lethal for the surrounding cells. In this work, we have shown that a novel class of oligo-p-phenylene ethynylenes (OPEs) exhibit selective binding and fluorescence turn-on in the presence of prefibrillar and fibrillar aggregates of disease-relevant proteins such as amyloid-β (Aβ) and α-synuclein. Concomitant with fluorescence turn-on, OPE also photosensitizes singlet oxygen under illumination through the generation of a triplet state, pointing to the potential application of OPEs as photosensitizers in PDT. Herein, we investigated the photosensitizing activity of an anionic OPE for the photo-oxidation of Aβ fibrils and compared its efficacy to the well-known but nonselective photosensitizer methylene blue (MB). Our results show that, while MB photo-oxidized both monomeric and fibrillar conformers of Aβ40, OPE oxidized only Aβ40 fibrils, targeting two histidine residues on the fibril surface and a methionine residue located in the fibril core. Oxidized fibrils were shorter and more dispersed but retained the characteristic β-sheet rich fibrillar structure and the ability to seed further fibril growth. Importantly, the oxidized fibrils displayed low toxicity. We have thus discovered a class of novel theranostics for the simultaneous detection and oxidization of amyloid aggregates. Importantly, the selectivity of OPE’s photosensitizing activity overcomes the limitation of off-target oxidation of traditional photosensitizers and represents an advancement of PDT as a viable strategy to treat neurodegenerative disorders.

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Research Organization:: Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

Sponsoring Organization:: USDOE Office of Science (SC). Office of Basic Energy Sciences (BES); USDOE National Nuclear Security Administration (NNSA); National Science Foundation (NSF); Defense Threat Reduction Agency (DTRA)

Grant/Contract Number:: 89233218CNA000001; ACI-1053575; 1605225; 1207362; 1560058; HDTRA1-08-1-0053

OSTI ID:: 1879388

Report Number(s):: LA-UR-21-30971

Journal Information:: ACS Applied Materials and Interfaces, Vol. 14, Issue 13; ISSN 1944-8244

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Alzheimer’s disease
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oligo-p-phenylene ethylene
photo-oxidation
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Title: Controlled and Selective Photo-oxidation of Amyloid-β Fibrils by Oligomeric p-Phenylene Ethynylenes

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