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Synlett 2024; 35(08): 920-924
DOI: 10.1055/a-2182-7614
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Special Issue dedicated to Keith Fagnou

Rose Bengal Promoted Catalytic Amyloid-β Oxygenation by Sonoactivation

Wataru Atsumi
a   Laboratory of Synthetic Organic Chemistry, Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
,
Keiichi Kawabata
a   Laboratory of Synthetic Organic Chemistry, Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
,
Mina Yamane
a   Laboratory of Synthetic Organic Chemistry, Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
,
Miku Oi
a   Laboratory of Synthetic Organic Chemistry, Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
,
Harunobu Mitsunuma
a   Laboratory of Synthetic Organic Chemistry, Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
b   JST, PRESTO, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan
,
Youhei Sohma∗
c   Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Wakayama Medical University, 25-1 Shichibacho, Wakayama, 640-8156, Japan
,
Yukiko Hori∗
d   Laboratory of Neuropathology and Neuroscience, Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
,
Taisuke Tomita∗
d   Laboratory of Neuropathology and Neuroscience, Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
,
Motomu Kanai  ∗
a   Laboratory of Synthetic Organic Chemistry, Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
› Author AffiliationsWe thank JSPS KAKENHI Grant Numbers JP23H05466 (M.K.), JP21H02602 (Y.S.), JP23H00394 (T.T.), JP18K06653, JP21H02622, JP18K06653, JP21H02622, and JP22H05036 (Y.H.), JP20H05843 (Dynamic Exciton) and 23K06045 (H.M.), JP21K20727 (T.S.), AMED Grant Numbers JP19dm0107106, JP19dm0307030, JP19jm0210058 (Y.S.), and JP22gm6410017 (Y.H.), JST, PRESTO Grant Number JPMJPR2279 (H.M.), and the University of Tokyo Gap Fund Program (T.T.). M.O. and M.Y. acknowledge a JSPS Research Fellowship for Young Scientists.
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Dedicated to the memory of Professor Keith Fagnou

Abstract

Catalytic photooxygenation of amyloid-β is a leading therapeutic strategy for the treatment of Alzheimer disease; however, the limited tissue permeability of light hampers its clinical application. We here report an alternative catalytic sonooxygenation strategy to circumvent this problem. Amyloid-β aggregates were oxygenated by using rose bengal as a sonosensitizer under ultrasound irradiation. Structure–activity relationships revealed that xanthene-derived catalysts containing halogen atoms furnished a superior amyloid oxygenation activity.

Key words

Alzheimer disease - amyloid-β - amyloid oxygenation - ultrasound - sonodynamic therapy - sonosensitization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2182-7614.
  • Supporting Information


Publication History

Received: 31 August 2023

Accepted after revision: 27 September 2023

Accepted Manuscript online:
27 September 2023

Article published online:
30 October 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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