苯并双噻二唑光热剂合成及抗肿瘤活性研究

doi:10.3969/j.issn.1000-1565.2026.03.009

摘要/Abstract

摘要： 采用醚化、偶联、亲核取代和季铵化等反应,合成了一种新型水溶性苯并双噻二唑光热剂(BBTD-PTA). 采用紫外-可见-近红外吸收光谱和稳态荧光光谱研究了其光物理性质. 采用808 nm激光器与红外热成像仪联用测定了其光热性质. 以人肝癌细胞Hep G2作为模型,用MTT比色法评估了BBTD-PTA的生物相容性和光热治疗能力. 结果表明:BBTD-PTA分子具有良好的近红外光吸收及发射能力,其光热转换效率为53.1%. BBTD-PTA分子具有较高的生物相容性,可在808 nm激光照射下显著降低肿瘤细胞的活力,表明BBTD-PTA分子是一种潜在的高效抗肿瘤光热剂.

关键词: 苯并双噻二唑, 光热剂, 抗肿瘤

Abstract: A novel water-soluble benzobisthiadiazole molecule(BBTD-PTA)as a photothermal agent was synthesized by etherification, coupling, nucleophilic substitution and quaternization. The photophysical properties were analyzed by UV-Vis-NIR absorption spectrum and steady-state fluorescence spectrum. The photothermal conversion properties were measured by a semiconductor laser combined with an infrared thermal imager. Hep G2 hepatoma cells were used as a model to evaluate the biocompatibility and photothermal therapy effect by MTT assay. The results showed that BBTD-PTA molecule was of capability of near-infrared absorption and emission. Its photothermal conversion efficiency reached 53.1%. - 引用格式:张文恺,杨术明,马永龙,等.基于EDEM的牧场推料机器人参数优化设计与试验［J］.河北大学学报(自然科学版),2026,46(3):225-236.引用格式:郭振鹏,杨魁,黄腾璇,等.苯并双噻二唑光热剂合成及抗肿瘤活性研究［J］.河北大学学报(自然科学版),2026,46(3):310-317.DOI:10.3969/j.issn.1000-1565.2026.03.009苯并双噻二唑光热剂合成及抗肿瘤活性研究郭振鹏,杨魁,黄腾璇,李玮(河北大学化学与材料科学学院,药物化学与分子诊断教育部重点实验室,河北保定 071000)摘要:采用醚化、偶联、亲核取代和季铵化等反应,合成了一种新型水溶性苯并双噻二唑光热剂(BBTD-PTA). 采用紫外-可见-近红外吸收光谱和稳态荧光光谱研究了其光物理性质. 采用808 nm激光器与红外热成像仪联用测定了其光热性质. 以人肝癌细胞Hep G2作为模型,用MTT比色法评估了BBTD-PTA的生物相容性和光热治疗能力. 结果表明:BBTD-PTA分子具有良好的近红外光吸收及发射能力,其光热转换效率为53.1%. BBTD-PTA分子具有较高的生物相容性,可在808 nm激光照射下显著降低肿瘤细胞的活力,表明BBTD-PTA分子是一种潜在的高效抗肿瘤光热剂.关键词:苯并双噻二唑; 光热剂; 抗肿瘤中图分类号:TP242.3 文献标志码:A 文章编号:1000-1565(2026)03-0310-08DOI:10.3969/j.issn.1000-1565.2026.03.009Synthesis and study on in vitro anti-tumor activity of benzodithiadiazole photothermal agentGUO Zhenpeng, YANG Kui, HUANG Tengxuan, LI Wei(Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, College of Chemistry and Materials Science, Hebei University, Baoding 071000, China)Abstract: A novel water-soluble benzobisthiadiazole molecule(BBTD-PTA)as a photothermal agent was synthesized by etherification, coupling, nucleophilic substitution and quaternization. The photophysical properties were analyzed by UV-Vis-NIR absorption spectrum and steady-state fluorescence spectrum. The photothermal conversion properties were measured by a semiconductor laser combined with an infrared thermal imager. Hep G2 hepatoma cells were used as a model to evaluate the biocompatibility and photothermal therapy effect by MTT assay. The results showed that BBTD-PTA molecule was of capability of near-infrared absorption and emission. Its photothermal conversion efficiency reached 53.1%. - 收稿日期:2025-06-04;修回日期:2025-11-04 基金项目:河北省自然科学基金面上项目(B2023201031);先导药物分子绿色合成创新团队项目(IT2023B01);河北省化学生物学重点实验室项目(22567632H);河北省分析科学与技术重点实验室项目(22567620H) 第一作者:郭振鹏(1995—),男,河北大学在读博士研究生,主要从事荧光染料及其光学诊疗研究.E-mail:Guozhenpeng2025@163.com 通信作者:李玮(1963—),男,河北大学教授,主要从事化学生物学研究.E-mail:liwei2020@hbu.edu.cn 第3期郭振鹏等:苯并双噻二唑光热剂合成及抗肿瘤活性研究河北大学学报(自然科学版) 第46卷BBTD-PTA shows high biocompatibility and potent antitumor efficiacy under 808 nm laser irradiation, suggesting it is a promising candidate for efficient photothermal therapy.

Key words: benzobisthiadiazole, photothermal agent, anti-tumor

中图分类号:

TP242.3

郭振鹏,杨魁,黄腾璇,李玮. 苯并双噻二唑光热剂合成及抗肿瘤活性研究[J]. 河北大学学报(自然科学版), 2026, 46(3): 310-317.

GUO Zhenpeng, YANG Kui, HUANG Tengxuan, LI Wei. Synthesis and study on in vitro anti-tumor activity of benzodithiadiazole photothermal agent[J]. Journal of Hebei University(Natural Science Edition), 2026, 46(3): 310-317.

参考文献

[1] Zeng S, Gao H Q, Li C, et al. Boosting photothermal theranostics via TICT and molecular motions for photohyperthermia therapy of muscle-invasive bladder cancer[J]. Adv Healthc Mater, 2021, 10(24): 2101063. DOI:10.1002/adhm.202101063.
[2] Xu T T, Deng Y Y, Yu X Y, et al. Natural autophagy modulators in non-communicable diseases: from autophagy mechanisms to therapeutic potential[J]. Acta Pharmacol Sin, 2025, 46(1): 8-32. DOI:10.1038/s41401-024-01356-y.
[3] Yuan S Y, Zhou J, Wang J T, et al. Advances of photothermal agents with fluorescence imaging/enhancement ability in the field of photothermal therapy and diagnosis[J]. Mol Pharmaceutics, 2024, 21(2): 467-480. DOI:10.1021/acs.molpharmaceut.3c01073.
[4] Li Y, Qi H L, Geng Y J, et al. Research progress of organic photothermal agents delivery and synergistic therapy systems[J]. Colloids Surf B Biointerfaces, 2024, 234: 113743. DOI:10.1016/j.colsurfb.2024.113743.
[5] Gan S Q, Wu Y Z, Zhang X, et al. Recent advances in hydrogel-based phototherapy for tumor treatment[J]. Gels, 2023, 9(4): 286. DOI:10.3390/gels9040286.
[6] Yin C, Li X Z, Wang Y, et al. Organic semiconducting macromolecular dyes for NIR-II photoacoustic imaging and photothermal therapy[J]. Adv Funct Mater, 2021, 31(37): 2104650. DOI:10.1002/adfm.202104650.
[7] Yu J F, Li J L, Li M. An intramolecular rotor-bridged dimeric cyanine photothermal transducer for efficient near-infrared II fluorescence imaging-guided mitochondria-targeted phototherapy[J]. ACS Sens, 2024, 9(7): 3581-3593. DOI:10.1021/acssensors.4c00561.
[8] Ni Z J, Wang H L, Dong H L, et al. Mesopolymer synthesis by ligand-modulated direct arylation polycondensation towards n-type and ambipolar conjugated systems[J]. Nature Chem, 2019, 11(3): 271-277. DOI:10.1038/s41557-018-0200-y.
[9] Xu H, Han P B, Qin A J, et al. Recent advances and application prospects in photothermal materials [J]. Acta Chim Sin, 2023, 81(10): 1420. DOI:10.6023/a2305023211.
[10] Wang L C, Li N, Wang W L, et al. Benzobisthiadiazole-based small molecular near-infrared-II fluorophores: from molecular engineering to nanophototheranostics[J]. ACS Nano, 2024, 18(6): 4683-4703. DOI:10.1021/acsnano.3c12316.
[11] Zhang J Q, Xu X Y, Cao S Q, et al. Structures and applications of NIR-II AIEgens containing benzobisthiadiazole derivatives[J]. Eur J Org Chem, 2022, 2022(44): e202201131. DOI:10.1002/ejoc.202201131.
[12] Yang Q L, Ma Z R, Wang H S, et al. Rational design of molecular fluorophores for biological imaging in the NIR-II window[J]. Adv Mater, 2017, 29(12): 1605497. DOI:10.1002/adma.201605497.
[13] Zeng L R, Pan B W, Cai J, et al. Construction, structural modification, and bioactivity evaluation of pentacyclic triterpenoid privileged scaffolds in active natural products[J]. RSC Adv, 2024, 14(53): 39436-39461. DOI:10.1039/d4ra07602h.
[14] Liu B K, Zheng J, Wang H, et al. BODIPY-based photosensitizers with simultaneous photodynamic antitumor and antibacterial effects[J]. Mater Chem Front, 2023, 7(22): 5879-5890. DOI:10.1039/d3qm00753g.
[15] Králová J, Jurásˇek M, Miksˇátková L, et al. Influence of fluorophore and linker length on the localization and trafficking of fluorescent sterol probes[J]. Sci Rep, 2020, 10: 22053. DOI:10.1038/s41598-020-78085-9.
[16] Shao W, Wei Q L, Wang S F, et al. Molecular engineering of D-A-D conjugated small molecule nanoparticles for high performance NIR-II photothermal therapy[J]. Mater Horiz, 2020, 7(5): 1379-1386. DOI:10.1039/c9mh00660e.
[17] Taylor M L, Wilson R E Jr, Amrhein K D, et al. Gold nanorod-assisted photothermal therapy and improvement strategies[J]. Bioengineering, 2022, 9(5): 200. DOI:10.3390/bioengineering9050200.
[18] Yang Y, Chen M, Wu Y J, et al. Ultrasound assisted one-step synthesis of Au@Pt dendritic nanoparticles with enhanced NIR absorption for photothermal cancer therapy[J]. RSC Adv, 2019, 9(49): 28541-28547. DOI:10.1039/c9ra04286e. (