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Highly Photostable Deep-NIR Chromophore with a Superior Molar Absorptivity for Efficient Photothermal Therapy
Industrial & Engineering Chemistry Research ( IF 3.8 ) Pub Date : 2024-01-11 , DOI: 10.1021/acs.iecr.3c04300 Xicun Lu 1 , Lei Yin 1 , Xiaoli Zhuang 1 , Ruwei Wei 1 , Cheng Yao 1 , Yuyang Zhang 1 , Yuze Wang 2 , Xiao Luo 2 , Xuhong Qian 1, 2 , Youjun Yang 1
Industrial & Engineering Chemistry Research ( IF 3.8 ) Pub Date : 2024-01-11 , DOI: 10.1021/acs.iecr.3c04300 Xicun Lu 1 , Lei Yin 1 , Xiaoli Zhuang 1 , Ruwei Wei 1 , Cheng Yao 1 , Yuyang Zhang 1 , Yuze Wang 2 , Xiao Luo 2 , Xuhong Qian 1, 2 , Youjun Yang 1
Affiliation
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Organic chromophores, especially those absorbing/emitting in the deep near-infrared region (deep-NIR, i.e., 800 nm and beyond), have prominent potentials in photothermal cancer therapy due to the deep tissue penetration and good biocompatibility. Although many cyanine/DAD-based photothermal agents have been successfully used in clinical and preclinical trials, they are limited to poor photostability and poor molar absorptivity. There is still an imperative demand for robust deep-NIR photothermal agents exhibiting high photostability and high molar absorptivity. We previously invented a bright push–pull fluorochromic scaffold (EC5) absorbing and emitting in the deep-NIR spectral region. In this work, EC5 was rationally tailored to suppress its fluorescence emission and promote its photothermal conversion efficiency. This led to the design and synthesis of EC5PM and EC5DP by changing two or four of its N-alkyl groups of the push–pull headgroups of EC5 into phenyl groups, respectively. The fluorescence intensities of EC5PM and EC5DP are completely quenched due to the TICT effect associated with the N–Ph bonds. In particular, EC5DP maximally absorbs at a longer wavelength of 879 nm with a superior photostability, a high photothermal conversion efficiency of 54.8%, and a superior molar extinction coefficient of 224,000 M–1 cm–1. Upon encapsulation in DSPE-mPEG2000 micelles, the phototoxicity of EC5DP was showcased in 4T1 cells and a remarkable therapeutic effect of tumors was showcased with a 4T1 tumor-bearing mouse model. This work provides a rational strategy to design ultraphotostable and highly deep-NIR absorbing organic chromophores for photothermal therapy.
中文翻译：
高度光稳定的深近红外发色团，具有卓越的摩尔吸收率，可实现高效光热治疗
有机发色团，特别是那些在深近红外区域（深NIR，即800 nm及以上）吸收/发射的有机发色团，由于其深层组织穿透性和良好的生物相容性，在光热癌症治疗中具有突出的潜力。尽管许多基于花青/DAD的光热剂已成功用于临床和临床前试验，但它们仅限于光稳定性差和摩尔吸收率差。人们仍然迫切需要具有高光稳定性和高摩尔吸收率的强大的深近红外光热剂。我们之前发明了一种明亮的推拉荧光变色支架（EC5），在深近红外光谱区域吸收和发射。在这项工作中，EC5被合理定制以抑制其荧光发射并提高其光热转换效率。这导致了通过将EC5推拉头基的两个或四个N-烷基分别改变为苯基来设计和合成EC5PM和EC5DP。由于与 N-Ph 键相关的 TICT 效应，EC5PM和EC5DP的荧光强度被完全猝灭。特别是，EC5DP在879 nm的较长波长处具有最大吸收，具有优异的光稳定性、54.8%的高光热转换效率和224,000 M –1 cm –1的优异摩尔消光系数。将EC5DP封装在 DSPE-mPEG2000 胶束中后，在 4T1 细胞中表现出光毒性，并在 4T1 荷瘤小鼠模型中表现出显着的肿瘤治疗效果。这项工作为设计用于光热疗法的超光稳定和高度深近红外吸收的有机发色团提供了合理的策略。
更新日期：2024-01-11
中文翻译：
高度光稳定的深近红外发色团，具有卓越的摩尔吸收率，可实现高效光热治疗
有机发色团，特别是那些在深近红外区域（深NIR，即800 nm及以上）吸收/发射的有机发色团，由于其深层组织穿透性和良好的生物相容性，在光热癌症治疗中具有突出的潜力。尽管许多基于花青/DAD的光热剂已成功用于临床和临床前试验，但它们仅限于光稳定性差和摩尔吸收率差。人们仍然迫切需要具有高光稳定性和高摩尔吸收率的强大的深近红外光热剂。我们之前发明了一种明亮的推拉荧光变色支架（EC5），在深近红外光谱区域吸收和发射。在这项工作中，EC5被合理定制以抑制其荧光发射并提高其光热转换效率。这导致了通过将EC5推拉头基的两个或四个N-烷基分别改变为苯基来设计和合成EC5PM和EC5DP。由于与 N-Ph 键相关的 TICT 效应，EC5PM和EC5DP的荧光强度被完全猝灭。特别是，EC5DP在879 nm的较长波长处具有最大吸收，具有优异的光稳定性、54.8%的高光热转换效率和224,000 M –1 cm –1的优异摩尔消光系数。将EC5DP封装在 DSPE-mPEG2000 胶束中后，在 4T1 细胞中表现出光毒性，并在 4T1 荷瘤小鼠模型中表现出显着的肿瘤治疗效果。这项工作为设计用于光热疗法的超光稳定和高度深近红外吸收的有机发色团提供了合理的策略。
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