Citation: Jichao XU, Ming HU, Xichang CHEN, Chunhui WANG, Leichen WANG, Lingyi ZHOU, Xing HE, Xiamin CHENG, Su JING. Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate[J]. Chinese Journal of Inorganic Chemistry, ;2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144 shu

Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate

  • Corresponding author: Su JING, sjing@njtech.edu.cn
  • Received Date: 26 April 2025
    Revised Date: 15 May 2025

Figures(9)

  • This article reports the rational design of a chemodynamic prodrug, FcNH-SeNBD. The prodrug was constructed by coupling ferrocene with benzoselenadiazole (SeNBD). By taking advantage of the elevated level of H2O2 in cancer cells, FcNH-SeNBD could generate cytotoxic ·OH radicals to induce cancer cell apoptosis and remain non-toxic in normal cells. In the meantime, the oxidation of ferrocene may interrupt its photo-induced electron transfer to SeNBD and facilitate the fluorescence recovery, thereby enabling FcNH-SeNBD for cancer cell imaging. FcNH-SeNBD was cytotoxic against liver cancer cell line HepG2 [IC50=(7.95±0.98) μg·mL-1] and colon cancer cell line HCT116 [IC50=(15.74±1.5) μg·mL-1], while displayed minimum toxicity to normal epithelial colonic cell line NCM- 460 (IC50>100 μg·mL-1), demonstrating its selective toxicity to cancer cell line. Mechanistic investigations revealed that FcNH-SeNBD was able to induce cancer cell apoptosis through caspase-3-dependent pathways. Moreover, a cell imaging study confirmed the strong red fluorescence signal of FcNH-SeNBD upon internalization and subsequent activation in tumor cells.
  • 加载中
    1. [1]

      HAO J N, GE K M, CHEN G L, DAI B, LI Y S. Strategies to engineer various nanocarrier-based hybrid catalysts for enhanced chemodynam- ic cancer therapy[J]. Chem. Soc. Rev., 2023,527707.

    2. [2]

      YANG N, XIAO W Y, SONG X J, WANG W J, DONG X C. Recent advances in tumor microenvironment hydrogen peroxide-responsive materials for cancer photodynamic therapy[J]. Nano-Micro Lett., 2020,1215.

    3. [3]

      HILLARD E, VESSIèRES A, THOUIN L, JAOUEN G, AMATORE C. Ferrocene-mediated proton-coupled electron transfer in a series of ferrocifen-type breast-cancer drug candidates[J]. Angew. Chem.-Int. Edit., 2006,45:285-290.

    4. [4]

      PAYEN O, TOP S, VESSIÈRES A, BRULÉ E, MARIE-AUDE P, MCGLINCHEY M J, MÜLLER-BUNZ H, JAOUEN G. Synthesis and structure- activity relationships of the first ferrocenyl- aryl-hydantoin derivatives of the nonsteroidal antiandrogen nilutamide[J]. J. Med. Chem., 2008,51:1791-1799.

    5. [5]

      WANG Y, DANSETTE P M, PIGEON P, TOP S, MCGLINCHEY M, MANSUY D, JAOUEN G. A new generation of ferrociphenols leads to a great diversity of reactive metabolites, and exhibits remarkable antiproliferative properties[J]. Chem. Sci., 2018,9:70-78.

    6. [6]

      ZHOU H Y, LI M, QU J, JING S, XU H, ZHAO J Z, ZHANG J, HE M F. Effective antitumor candidates based upon ferrocenylseleno-dopa-mine derivatives: Growth inhibition by induction cell apoptosis and antivascular effects[J]. Organometallics, 2016,35:1866-1875.

    7. [7]

      ZHANG C, WU W, LI R Q, QIU W X, ZHUANG Z N, CHENG S X, ZHANG X Z. Peptide-based multifunctional nanomaterials for tumor imaging and therapy[J]. Adv. Funct. Mater., 2018,281804492.

    8. [8]

      TANG Z M, LIU Y Y, HE M Y, BU W B. Chemodynamic therapy: Tumour microenvironment-mediated Fenton and Fenton-like reactions[J]. Angew. Chem.-Int. Edit., 2019,58:946-956.

    9. [9]

      TANG Z M, ZHAO P R, WANG H, LIU Y Y, BU W B. Biomedicine meets fenton chemistry[J]. Chem. Rev., 2021,121:1981-2019.

    10. [10]

      SHARMA A, VERWILST P, LI M L, MA D D, SINGH N, YOO J Y, KIM Y J, YANG Y, ZHU J H, HUANG H Q, HU X L, HE X P, ZENG L T, JAMES T D, PENG X J, SESSLER J L, KIM J S. Theranostic fluorescent probes[J]. Chem Rev., 2024,124:2699-2804.

    11. [11]

      ZHANG J J, NING L L, HUANG J G, ZHANG C, PU K Y. Activatable molecular agents for cancer theranostics[J]. Chem. Sci., 2020,11:618-630.

    12. [12]

      TAN J Y, DUAN X H, ZHANG F, BAN X H, MAO J J, CAO M H, HAN S S, SHUAI X T, SHEN J. Theranostic nanomedicine for synergistic chemodynamic therapy and chemotherapy of orthotopic glioma[J]. Adv. Sci., 2020,72003036.

    13. [13]

      WANG N N, ZENG Q, ZHANG R J, XING D, ZHANG T. Eradication of solid tumors by chemodynamic theranostics with H2O2-catalyzed hydroxyl radical burst[J]. Theranostics, 2021,11:2334-2348.

    14. [14]

      RUBERTE A C, SANMARTIN C, AYDILLO C, SHARMA A K, PLANO D. Development and therapeutic potential of selenazo compounds[J]. J. Med. Chem., 2020,63:1473-1489.

    15. [15]

      WANG J P, CHEN M K, ZHANG Z Y, MA L, CHEN T F. Selenium: From fluorescent probes to biomedical application[J]. Coord. Chem. Rev., 2023,493215278.

    16. [16]

      IDRIS I, TANNOUX T, DERRIDJ F, DORCET V, BOIXEL J, GUERCHAIS V, SOULÉ J F, DOUCET H. Effective modulation of the photoluminescence properties of 2, 1, 3-benzothiadiazoles and 2, 1, 3-benzoselenadiazoles by Pdcatalyzed C-H bond arylations[J]. J. Mater. Chem. C, 2018,6:1731-1737.

    17. [17]

      BENSON S, FERNANDEZ A, BARTH N D, MOLINER F D, HORROCKS M H, HERRINGTON C S, ABAD J L, DELGADO A, KELLY L, CHANG Z Y, FENG Y, NISHIURA M, HORI Y, KIKUCHI K, VENDRELL M. SCOTfluors: Small, conjugatable, orthogonal, and tunable fluorophores for in vivo imaging of cell metabolism[J]. Angew. Chem.-Int. Edit., 2019,58:6911-6915.

    18. [18]

      GAO Y, WANG C, CHI W J, LIU X G. Molecular origins of heteroatom engineering on the emission wavelength tuning, quantum yield variations and fluorogenicity of NBD-like SCOTfluors[J]. Chem. ‒ Asian J., 2020,15:4082-4086.

    19. [19]

      ZHOU L Y, LUO F J, CHI W J, TANG Y P, LIU X G, LIN Q L. Activatable selenium-containing fluorescent apoptotic agent for biosensing and tracing cancer cell apoptosis[J]. Sens. Actuator B Chem., 2020,311127915.

    20. [20]

      QU J, XIA Q, JI W, JING S, ZHU D Y, LI L, HUANG L, AN Z F, XIN C Q, NI Y, LI M X, JIA J D, SONG Y L, HUANG W. A ferrocene∩europium assembly showing phototriggered anticancer activity and fluorescent modality imaging[J]. Dalton Trans., 2018,47:1479-1487.

    21. [21]

      WANG R Q, ZHOU T, LI A M, QU J, ZHANG X, ZHU X F, JING S. The design of fluorescein-ferrocene derivatives as HOCl-triggered turn-on fluorescent probes and anticancer prodrugs[J]. Dalton Trans., 2022,51:15330-15338.

    22. [22]

      ZHANG L, WANG C H, LI Y Y, WANG H Y, SUN K H, LU S Y, WANG Y H, JING S, CORDES T. Modular design and scaffold-synthesis of multi-functional fluorophores for targeted cellular imaging and pyroptosis[J]. Angew. Chem.-Int. Edit., 2025,64e202415627.

    23. [23]

      LIU X L, LI M G, HAN T, CAO B, QIU Z J, LI Y Y, LI Q Y, HU Y B, LIU Z Y, LAM J W Y, HU X L, TANG B Z. In-situ generation of azonia-containing polyelectrolytes for luminescent photopatterning and superbug killing[J]. J. Am. Chem. Soc., 2019,141:11259-11268.

    24. [24]

      DONG S M, XU J T, JIA T, XU M S, ZHONG C N, YANG G X, LI J R, YANG D, HE F, GAI S L, YANG P P, LIN J. Upconversion-mediated ZnFe2O4 nanoplatform for NIR-enhanced chemodynamic and photodynamic therapy[J]. Chem. Sci., 2019,10:4259-4271.

    25. [25]

      LIU X C, ZHOU Y Y, ZHANG J C, LUO L, YANG Y, HUANG H L, PENG H, TANG L, MU Y. Insight into electro-fenton and photo-fenton for the degradation of antibiotics: Mechanism study and research gaps[J]. Chem. Eng. J., 2018,347:379-397.

    26. [26]

      RANJAN A, SHARMA D, SRIVASTAVA A K, VARMA A, MAGANI S K J, JOSHI R K. Evaluation of anticancer activity of ferrocene based benzothiazole and β-ketooxothioacetal[J]. J. Organomet. Chem., 2022,979122500.

    27. [27]

      SAHOO G, SAMAL D, KHANDAYATARAY P, MURTHY M K. A review on caspases: Key regulators of biological activities and apoptosis[J]. Mol. Neurobiol., 2023,60:5805-5837.

    28. [28]

      MCLLWAIN D R, BERGER T, MAK T W. Caspase functions in cell death and disease[J]. Cold Spring Harbor Perspect. Biol., 2013,5(4)a008656.

    29. [29]

      HU B, ZHANG Q, GAO X, XU K H, TANG B. Monitoring the activation of caspases-1/3/4 for describing the pyroptosis pathways of cancer cells[J]. Anal. Chem., 2021,93:12022-12031.

  • 加载中
    1. [1]

      Guilan He Yaofeng Yuan . 手性二茂铁双膦配体Xyliphos的合成及应用. University Chemistry, 2025, 40(8): 130-137. doi: 10.12461/PKU.DXHX202409122

    2. [2]

      Siyi ZHONGXiaowen LINJiaxin LIURuyi WANGTao LIANGZhengfeng DENGAo ZHONGCuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093

    3. [3]

      Jianfeng Yan Yating Xiao Xin Zuo Caixia Lin Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005

    4. [4]

      Kexin Feng Jie Zhang Yujia Sun Qiong Ai Longchun Li . 乙酰二茂铁和二茂铁甲酰丙酮的合成、纯化及表征. University Chemistry, 2025, 40(8): 307-314. doi: 10.12461/PKU.DXHX202409045

    5. [5]

      Fa Wang Yu Chen Hui Chao . Ruthenium(II) Complexes as Photoactivated Chemo-Prodrugs for Hypoxic Tumor Therapy. University Chemistry, 2025, 40(7): 200-212. doi: 10.12461/PKU.DXHX202410024

    6. [6]

      Jiageng Li Putrama . 数值积分耦合非线性最小二乘法一步确定反应动力学参数. University Chemistry, 2025, 40(6): 364-370. doi: 10.12461/PKU.DXHX202407098

    7. [7]

      Caixia Lin Zhaojiang Shi Yi Yu Jianfeng Yan Keyin Ye Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005

    8. [8]

      Yue Wu Jun Li Bo Zhang Yan Yang Haibo Li Xian-Xi Zhang . Research on Kinetic and Thermodynamic Transformations of Organic-Inorganic Hybrid Materials for Fluorescent Anti-Counterfeiting Application information: Introducing a Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(6): 390-399. doi: 10.3866/PKU.DXHX202403028

    9. [9]

      Yue WANGZhizhi GUJingyi DONGJie ZHUCunguang LIUGuohan LIMeichen LUJian HANShengnan CAOWei WANG . Effects of kelp-derived carbon dots on embryonic development of zebrafish. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1209-1217. doi: 10.11862/CJIC.20230423

    10. [10]

      Liangzhen Hu Li Ni Ziyi Liu Xiaohui Zhang Bo Qin Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001

    11. [11]

      Yonghui ZHOURujun HUANGDongchao YAOAiwei ZHANGYuhang SUNZhujun CHENBaisong ZHUYouxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373

    12. [12]

      Shiyang HeDandan ChuZhixin PangYuhang DuJiayi WangYuhong ChenYumeng SuJianhua QinXiangrong PanZhan ZhouJingguo LiLufang MaChaoliang Tan . Pt Single-Atom-Functionalized 2D Al-TCPP MOF Nanosheets for Enhanced Photodynamic Antimicrobial Therapy. Acta Physico-Chimica Sinica, 2025, 41(5): 100046-0. doi: 10.1016/j.actphy.2025.100046

    13. [13]

      Yanglin JiangMingqing ChenMin LiangYige YaoYan ZhangPeng WangJianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 2309027-0. doi: 10.3866/PKU.WHXB202309027

    14. [14]

      Xiuyun Wang Jiashuo Cheng Yiming Wang Haoyu Wu Yan Su Yuzhuo Gao Xiaoyu Liu Mingyu Zhao Chunyan Wang Miao Cui Wenfeng Jiang . Improvement of Sodium Ferric Ethylenediaminetetraacetate (NaFeEDTA) Iron Supplement Preparation Experiment. University Chemistry, 2024, 39(2): 340-346. doi: 10.3866/PKU.DXHX202308067

    15. [15]

      Shuhui Li Rongxiuyuan Huang Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028

    16. [16]

      Jinfu Ma Hui Lu Jiandong Wu Zhongli Zou . Teaching Design of Electrochemical Principles Course Based on “Cognitive Laws”: Kinetics of Electron Transfer Steps. University Chemistry, 2024, 39(3): 174-177. doi: 10.3866/PKU.DXHX202309052

    17. [17]

      Yeyun Zhang Ling Fan Yanmei Wang Zhenfeng Shang . Development and Application of Kinetic Reaction Flasks in Physical Chemistry Experimental Teaching. University Chemistry, 2024, 39(4): 100-106. doi: 10.3866/PKU.DXHX202308044

    18. [18]

      Aidang Lu Yunting Liu Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029

    19. [19]

      Baohua LÜYuzhen LI . Anisotropic photoresponse of two-dimensional layered α-In2Se3(2H) ferroelectric materials. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1911-1918. doi: 10.11862/CJIC.20240105

    20. [20]

      Dexin Tan Limin Liang Baoyi Lv Huiwen Guan Haicheng Chen Yanli Wang . Exploring Reverse Teaching Practices in Physical Chemistry Experiment Courses: A Case Study on Chemical Reaction Kinetics. University Chemistry, 2024, 39(11): 79-86. doi: 10.12461/PKU.DXHX202403048

Metrics
  • PDF Downloads(0)
  • Abstract views(3)
  • HTML views(1)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return