TY - JOUR
T1 - Design of Photostable, Activatable Near-Infrared Photoacoustic Probes Using Tautomeric Benziphthalocyanine as a Platform
AU - Toriumi, Naoyuki
AU - Asano, Norihito
AU - Ikeno, Takayuki
AU - Muranaka, Atsuya
AU - Hanaoka, Kenjiro
AU - Urano, Yasuteru
AU - Uchiyama, Masanobu
N1 - Funding Information:
This work was partly supported by JSPS KAKENHI (S) (No. 17H06173) (to M.U.), JSPS KAKENHI (No. 16H05099 and 18H04609) (to K.H.), and JSPS Research Fellowships for Young Scientists (to N.T.).
Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2019/6/3
Y1 - 2019/6/3
N2 - Near-infrared (NIR) imaging techniques have attracted significant attention for biological and medicinal applications due to the ability of NIR to penetrate deeply into tissues. However, there are very few stable, activatable molecular probes that can utilize NIR light in the wavelength range beyond 800 nm. Herein, we report a new activatable NIR system for photoacoustic imaging based on tautomeric benziphthalocyanines (BPcs). We found that the existence of a free hydroxyl group is crucial for NIR absorption of BPcs. Synthesized water-soluble hydroxy BPcs exhibited high photostability and no fluorescence, which are desirable features for photoacoustic imaging. We synthesized BPcs in which the free hydroxyl group was masked by an esterase-labile or an H2O2-labile group. The photoacoustic signals of these hydroxy-masked BPcs were increased upon NIR excitation at 880 nm in the presence of esterase or H2O2, respectively. These are rare examples of activatable probes utilizing NIR light at around 900 nm.
AB - Near-infrared (NIR) imaging techniques have attracted significant attention for biological and medicinal applications due to the ability of NIR to penetrate deeply into tissues. However, there are very few stable, activatable molecular probes that can utilize NIR light in the wavelength range beyond 800 nm. Herein, we report a new activatable NIR system for photoacoustic imaging based on tautomeric benziphthalocyanines (BPcs). We found that the existence of a free hydroxyl group is crucial for NIR absorption of BPcs. Synthesized water-soluble hydroxy BPcs exhibited high photostability and no fluorescence, which are desirable features for photoacoustic imaging. We synthesized BPcs in which the free hydroxyl group was masked by an esterase-labile or an H2O2-labile group. The photoacoustic signals of these hydroxy-masked BPcs were increased upon NIR excitation at 880 nm in the presence of esterase or H2O2, respectively. These are rare examples of activatable probes utilizing NIR light at around 900 nm.
KW - dyes/pigments
KW - near-infrared spectroscopy
KW - photoacoustic imaging
KW - phthalocyanines
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U2 - 10.1002/anie.201903303
DO - 10.1002/anie.201903303
M3 - Article
C2 - 30957388
AN - SCOPUS:85065392761
SN - 1433-7851
VL - 58
SP - 7788
EP - 7791
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 23
ER -