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
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.
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.
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Although rose bengal has been reported to induce cancer cell death at 100 μM, the concentration used in this study was 10 μM, which is outside the range of toxicity. For the toxicity of rose bengal, see:
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17 Under the optimized conditions (5 W/cm2, 20 min), the temperature rose by approximately 15 °C. However, under attenuated conditions (e.g., 1 W/cm2, 10 min), the temperature rise was almost negligible, whereas the oxygenation yield did not significantly decrease. We therefore conclude that the contribution of temperature increase to the oxygenation reaction is minor.
23 For the preprint version of this manuscript, see:
Atsumi W,
Kawabata K,
Yamane M,
Oi M,
Mitsunuma H,
Sohma Y,
Hori Y,
Tomita T,
Kanai M.
ChemRxiv 2023; preprint; DOI
