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一种咔唑功能化半导体化合物作为无重原子的光敏剂用于治疗肺癌的光疗。

A carbazole functionalized semiconducting compound as a heavy atom free photosensitizer for phototherapy against lung cancer.

机构信息

Department of Thoracic Surgery, The First Hospital Affiliated to Soochow University, Soochow University, 215301, P. R. China.

出版信息

J Mater Chem B. 2020 Dec 21;8(47):10764-10769. doi: 10.1039/d0tb02314k. Epub 2020 Nov 12.

DOI:10.1039/d0tb02314k
PMID:33179712
Abstract

Semiconducting compounds with high photostability and excellent photothermal ability are potential candidates for phototheranostics. In this paper, the heavy atom free compound 3,6-bis(5-(4-(9H-carbazol-9-yl)phenyl)furan-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (denoted as DPPCz) has been designed and synthesized through a C-H activation coupling reaction. DPPCz has a high singlet oxygen quantum yield (O QY) of 40.3% in DCM. In addition, DPPCz NPs obtained by nanoprecipitation exhibit a high photothermal conversion efficiency (48.2%) in water. DPPCz NPs have a low half inhibitory concentration (IC) of 7.1 μg mL towards human lung cancer cells (A549) with irradiation while the dark toxicity is almost negligible even at high concentrations. Furthermore, in vivo photothermal imaging guided study demonstrates that these NPs are able to inhibit tumor growth with the help of laser. The H&E stained pictures of the normal tissues indicate the biosafety of DPPCz NPs in that no obvious damage was observed. Our results demonstrate that DPPCz NPs are potential semiconducting photosensitizers for phototheranostics.

摘要

具有高光稳定性和优异光热性能的半导体化合物是光热治疗的潜在候选物。在本文中,通过 C-H 活化偶联反应设计并合成了不含重原子的化合物 3,6-双(5-(4-(9H-咔唑-9-基)苯基)呋喃-2-基)-2,5-双(2-辛基十二烷基)吡咯并[3,4-c]吡咯-1,4(2H,5H)-二酮(表示为 DPPCz)。DPPCz 在 DCM 中的单线态氧量子产率(O QY)高达 40.3%。此外,通过纳米沉淀法获得的 DPPCz NPs 在水中表现出高的光热转换效率(48.2%)。DPPCz NPs 在光照下对人肺癌细胞(A549)的半抑制浓度(IC)低至 7.1 μg mL-1,而在高浓度下几乎没有暗毒性。此外,体内光热成像引导研究表明,这些 NPs 能够在激光的帮助下抑制肿瘤生长。H&E 染色的正常组织图片表明 DPPCz NPs 的生物安全性,因为没有观察到明显的损伤。我们的结果表明,DPPCz NPs 是用于光热治疗的潜在半导体光敏剂。

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