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Attachment of −tBu groups to aza-BODIPY core at 3,5-sites with ultra-large Stokes shift to enhance photothermal therapy through apoptosis mechanism

By the introduction of the −tBu groups into aza-BODIPY core, di-tert-butyl-substituted aza-BODIPYs at 3,5-sites (tBuazaBDPs) were prepared for the first time. Based on the X-ray analysis of CN-tBuazaBDP, this molecular structure is twisted. Near-infrared dye SMe-tBuazaBDP has the ultra-large Stokes...

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Autores principales: Li, Ran, Ren, Junyi, Zhang, Dongxiang, Lv, Meiheng, Wang, Zhan, Wang, Huan, Zhang, Shan, Du, Jianjun, Jiang, Xin-Dong, Wang, Guiling
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9527945/
https://www.ncbi.nlm.nih.gov/pubmed/36199559
http://dx.doi.org/10.1016/j.mtbio.2022.100446
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author Li, Ran
Ren, Junyi
Zhang, Dongxiang
Lv, Meiheng
Wang, Zhan
Wang, Huan
Zhang, Shan
Du, Jianjun
Jiang, Xin-Dong
Wang, Guiling
author_facet Li, Ran
Ren, Junyi
Zhang, Dongxiang
Lv, Meiheng
Wang, Zhan
Wang, Huan
Zhang, Shan
Du, Jianjun
Jiang, Xin-Dong
Wang, Guiling
author_sort Li, Ran
collection PubMed
description By the introduction of the −tBu groups into aza-BODIPY core, di-tert-butyl-substituted aza-BODIPYs at 3,5-sites (tBuazaBDPs) were prepared for the first time. Based on the X-ray analysis of CN-tBuazaBDP, this molecular structure is twisted. Near-infrared dye SMe-tBuazaBDP has the ultra-large Stokes shift (152 ​nm) in aza-BODIPY system, combining with the twisted intramolecular charge transfer and the free rotation of the −tBu groups at 3,5-sites. Although the barrier-free rotors of the distal −tBu groups in SMe-tBuazaBDP result in low fluorescence quantum yield, the photothermal conversion efficiency is markedly enhanced. SMe-tBuazaBDP nanoparticles with low power laser irradiation were proven to block cancer cell cycle, inhibit cancer cell proliferation, and induce cancer cell apoptosis in photothermal therapy (PTT). The strategy of “direct attachment of −tBu groups to aza-BODIPY core” gives a new design platform for a photothermal therapy agent.
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spelling pubmed-95279452022-10-04 Attachment of −tBu groups to aza-BODIPY core at 3,5-sites with ultra-large Stokes shift to enhance photothermal therapy through apoptosis mechanism Li, Ran Ren, Junyi Zhang, Dongxiang Lv, Meiheng Wang, Zhan Wang, Huan Zhang, Shan Du, Jianjun Jiang, Xin-Dong Wang, Guiling Mater Today Bio Full Length Article By the introduction of the −tBu groups into aza-BODIPY core, di-tert-butyl-substituted aza-BODIPYs at 3,5-sites (tBuazaBDPs) were prepared for the first time. Based on the X-ray analysis of CN-tBuazaBDP, this molecular structure is twisted. Near-infrared dye SMe-tBuazaBDP has the ultra-large Stokes shift (152 ​nm) in aza-BODIPY system, combining with the twisted intramolecular charge transfer and the free rotation of the −tBu groups at 3,5-sites. Although the barrier-free rotors of the distal −tBu groups in SMe-tBuazaBDP result in low fluorescence quantum yield, the photothermal conversion efficiency is markedly enhanced. SMe-tBuazaBDP nanoparticles with low power laser irradiation were proven to block cancer cell cycle, inhibit cancer cell proliferation, and induce cancer cell apoptosis in photothermal therapy (PTT). The strategy of “direct attachment of −tBu groups to aza-BODIPY core” gives a new design platform for a photothermal therapy agent. Elsevier 2022-09-29 /pmc/articles/PMC9527945/ /pubmed/36199559 http://dx.doi.org/10.1016/j.mtbio.2022.100446 Text en © 2022 The Authors https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Full Length Article
Li, Ran
Ren, Junyi
Zhang, Dongxiang
Lv, Meiheng
Wang, Zhan
Wang, Huan
Zhang, Shan
Du, Jianjun
Jiang, Xin-Dong
Wang, Guiling
Attachment of −tBu groups to aza-BODIPY core at 3,5-sites with ultra-large Stokes shift to enhance photothermal therapy through apoptosis mechanism
title Attachment of −tBu groups to aza-BODIPY core at 3,5-sites with ultra-large Stokes shift to enhance photothermal therapy through apoptosis mechanism
title_full Attachment of −tBu groups to aza-BODIPY core at 3,5-sites with ultra-large Stokes shift to enhance photothermal therapy through apoptosis mechanism
title_fullStr Attachment of −tBu groups to aza-BODIPY core at 3,5-sites with ultra-large Stokes shift to enhance photothermal therapy through apoptosis mechanism
title_full_unstemmed Attachment of −tBu groups to aza-BODIPY core at 3,5-sites with ultra-large Stokes shift to enhance photothermal therapy through apoptosis mechanism
title_short Attachment of −tBu groups to aza-BODIPY core at 3,5-sites with ultra-large Stokes shift to enhance photothermal therapy through apoptosis mechanism
title_sort attachment of −tbu groups to aza-bodipy core at 3,5-sites with ultra-large stokes shift to enhance photothermal therapy through apoptosis mechanism
topic Full Length Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9527945/
https://www.ncbi.nlm.nih.gov/pubmed/36199559
http://dx.doi.org/10.1016/j.mtbio.2022.100446
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