Citation: Yin Hao-Yan, Tang Juan, Zhang Jun-Long. Sulfur speciation defined subcellular localization of coumarin derivatives: Correlation of structural relationship to biological behaviors[J]. Chinese Chemical Letters, ;2018, 29(2): 267-270. doi: 10.1016/j.cclet.2017.10.007 shu

Sulfur speciation defined subcellular localization of coumarin derivatives: Correlation of structural relationship to biological behaviors

Beijing National Laboratory for Molecular Sciences, State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China

Corresponding author: Zhang Jun-Long, zhangjunlong@pku.edu.cn
Received Date: 29 June 2017
Revised Date: 30 September 2017
Accepted Date: 11 October 2017
Available Online: 16 February 2017

Figures(4)

Targeted-delivery is of great importance to molecular probes and drugs for cell biology study. Herein we reported 11 sulfur-containing coumarins as cell imaging probes. Different sulfur speciation of the 4 representative coumarins SC1-SC4 renders them significantly different subcellular localizations and cellular uptake pathways:SC1 containing thioether group located in lysosomes, while sulfoxide and sulfone compounds SC2 and SC3 distributed in the whole cell. Furthermore, the cationic sulfonium containing compound SC4 was internalized by clathrin-mediated endocytosis and localized at mitochondria. By analyzing the molecular parameters of all 11 coumarins, we found that different sulfur speciation affected their lipophilicity and electrostatic surface potential. These two key factors play roles in altering biological behaviors of the coumarins. The results revealed the importance of sulfur speciation on the physicochemical properties and thus subcellular localization of bioprobes. This is useful for designing new functional bioprobes.
- Fluorescent imaging,
- Sulfur speciation,
- Subcellular localization,
- Sulfonium,
- Mitochondria targeting,
- Electrostatic surface potential
1. [1]
  M. Calligaris, Coord. Chem. Rev. 248(2004) 351-375. doi: 10.1016/j.ccr.2004.02.005
2. [2]
  R. Bentley, Chem. Soc. Rev. 34(2005) 609-624. doi: 10.1039/b418284g
3. [3]
  C. Jacob, A. Anwar, Physiol. Plant 133(2008) 469-480. doi: 10.1111/j.1399-3054.2008.01080.x
4. [4]
  M.F. Ross, G.F. Kelso, F.H. Blaikie, et al., Biochem. 70(2005) 222-230(Mosc.).
5. [5]
  Y. Hai, J.J. Chen, P. Zhao, et al., Chem. Commun. 47(2011) 2435-2437. doi: 10.1039/C0CC04113K
6. [6]
  R.W. Horobin, F. Rashid-Doubell, J.D. Pediani, G. Milligan, Biotech. Histochem. 88(2013) 440-460. doi: 10.3109/10520295.2013.780634
7. [7]
  D. Xie, J. Jing, Y.B. Cai, et al., Chem. Sci. 5(2014) 2318. doi: 10.1039/c3sc53299b
8. [8]
  J. Lai, X.S. Ke, J. Tang, J.L. Zhang, Chin. Chem. Lett. 26(2015) 937-941. doi: 10.1016/j.cclet.2015.04.023
9. [9]
  S.H. Alamudi, R. Satapathy, J. Kim, et al., Nat. Commun. 7(2016) 11964. doi: 10.1038/ncomms11964
10. [10]
  W. Lee, W.S. Jenks, J. Org. Chem. 66(2001) 474-480. doi: 10.1021/jo0056141
11. [11]
  S. Malashikhin, N.S. Finney, J. Am. Chem. Soc. 130(2008) 12846-12847. doi: 10.1021/ja802989v
12. [12]
  P.R. Christensen, J.K. Nagle, A. Bhatti, M.O. Wolf, J. Am. Chem. Soc. 135(2013) 8109-8112. doi: 10.1021/ja401383q
13. [13]
  R.S. Kathayat, N.S. Finney, J. Am. Chem. Soc. 135(2013) 12612-12614. doi: 10.1021/ja407099a
14. [14]
  C.D. Cruz, P.R. Christensen, E.L. Chronister, et al., J. Am. Chem. Soc. 137(2015) 12552-12564. doi: 10.1021/jacs.5b05457
15. [15]
  P. Pahlavanlu, P.R. Christensen, J.A. Therrien, M.O. Wolf, J. Phys, Chem. C 120(2016) 70-77.
16. [16]
  E. Varathan, V. Subramanian, Phys. Chem. Chem. Phys.19(2017) 12002-12012. doi: 10.1039/C7CP00828G
17. [17]
  J. Jing, J.J. Chen, Y. Hai, et al., Chem. Sci. 3(2012) 3315. doi: 10.1039/c2sc20764h
18. [18]
  A. Leo, C. Hansch, D. Elkins, Chem. Rev. 71(1971) 525-616. doi: 10.1021/cr60274a001
19. [19]
  S. Manzetti, T. Lu, J. Phys, Org. Chem. 26(2013) 473-483.
20. [20]
  J.E. Heuser, J. Cell Biol. 108(1989) 389-400. doi: 10.1083/jcb.108.2.389
21. [21]
  M.G. Qaddoumi, H.J. Gukasyan, J. Davda, et al., Mol. Vis. 9(2003) 559-568.
22. [22]
  S. Davis, M.J. Weiss, J.R. Wong, et al., J. Biol. Chem. 260(1985) 13844-13850.
23. [23]
  B. Yameen, W.I. Choi, C. Vilos, et al., J. Control. Release 190(2014) 485-499. doi: 10.1016/j.jconrel.2014.06.038
24. [24]
  V.P. Torchilin, Annu. Rev. Biomed. Eng. 8(2006) 343-375. doi: 10.1146/annurev.bioeng.8.061505.095735
25. [25]
  L. Rajendran, H.J. Knolker, K. Simons, Nat. Rev. Drug Discov. 9(2010) 29-42. doi: 10.1038/nrd2897
26. [26]
  N.M. Sakhrani, H. Padh, Drug Des. Devel. Ther. 7(2013) 585-599.
27. [27]
  J. Tang, Y.B. Cai, J. Jing, J.L. Zhang, Chem. Sci. 6(2015) 2389-2397. doi: 10.1039/C4SC03824J
28. [28]
  J. Tang, D. Xie, H.Y. Yin, et al., Org. Biomol. Chem. 14(2016) 3360-3368. doi: 10.1039/C6OB00249H
1. [1]
  Panpan Wang , Hongbao Fang , Mengmeng Wang , Guandong Zhang , Na Xu , Yan Su , Hongke Liu , Zhi Su . A mitochondria targeting Ir(III) complex triggers ferroptosis and autophagy for cancer therapy: A case of aggregation enhanced PDT strategy for metal complexes. Chinese Chemical Letters, 2025, 36(1): 110099-. doi: 10.1016/j.cclet.2024.110099
2. [2]
  Zhiyu Yu , Xiang Luo , Cheng Zhang , Xin Lu , Xiaohui Li , Pan Liao , Zhongqiu Liu , Rong Zhang , Shengtao Wang , Zhiqiang Yu , Guochao Liao . Mitochondria-targeted carrier-free nanoparticles based on dihydroartemisinin against hepatocellular carcinoma. Chinese Chemical Letters, 2024, 35(10): 109519-. doi: 10.1016/j.cclet.2024.109519
3. [3]
  Xinyi Zhao , Yuai Duan , Zihan Liu , Hua Geng , Yaping Li , Zhongfeng Li , Tianyu Han . Mapping sweat pores for biometric identification based on a donor-acceptor hydrophilic fluorescent probe. Chinese Chemical Letters, 2025, 36(8): 110617-. doi: 10.1016/j.cclet.2024.110617
4. [4]
  Kuan Deng , Fei Yang , Zhi-Qi Cheng , Bi-Wen Ren , Hua Liu , Jiao Chen , Meng-Yao She , Le Yu , Xiao-Gang Liu , Hai-Tao Feng , Jian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464
5. [5]
  Jiao Chen , Zihan Zhang , Guojin Sun , Yudi Cheng , Aihua Wu , Zefan Wang , Wenwen Jiang , Fulin Chen , Xiuying Xie , Jianli Li . Benzo[4,5]imidazo[1,2-a]pyrimidine-based structure-inherent targeting fluorescent sensor for imaging lysosomal viscosity and diagnosis of lysosomal storage disorders. Chinese Chemical Letters, 2024, 35(11): 110050-. doi: 10.1016/j.cclet.2024.110050
6. [6]
  Fan Zheng , Runsha Xiao , Shuai Huang , Zhikang Chen , Chen Lai , Anyao Bi , Heying Yao , Xueping Feng , Zihua Chen , Wenbin Zeng . Accurate visualization colorectal cancer by monitoring viscosity variations with a novel mitochondria-targeted fluorescent probe. Chinese Chemical Letters, 2025, 36(2): 109876-. doi: 10.1016/j.cclet.2024.109876
7. [7]
  Junliang Zhou , Tian-Bing Ren , Lin Yuan . The strategy to improve the brightness of organic small-molecule fluorescent dyes for imaging. Chinese Chemical Letters, 2025, 36(8): 110644-. doi: 10.1016/j.cclet.2024.110644
8. [8]
  Qian Pang , Fangjun Huo , Yongkang Yue , Caixia Yin . ONOO⁻ and viscosity dual-response fluorescent probe for arthritis imaging in vivo. Chinese Chemical Letters, 2025, 36(9): 110713-. doi: 10.1016/j.cclet.2024.110713
9. [9]
  Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
10. [10]
  Rong-Nan Yi , Wei-Min He . Visible light/copper catalysis enabled radial type ring-opening of sulfonium salts. Chinese Chemical Letters, 2025, 36(4): 110787-. doi: 10.1016/j.cclet.2024.110787
11. [11]
  Ying Chen , Lun Li , Guohao Han , Ren Liu , Guanghui An , Yi Zhu . Macromolecular coumarin sulfonium salt with side chain effect constructed by copolymerization strategy for free radical, cationic, and hybrid photopolymerizations. Chinese Chemical Letters, 2025, 36(7): 110458-. doi: 10.1016/j.cclet.2024.110458
12. [12]
  Yingxiao Gao , Feng Feng , Ting Luo , Yusong Han , Mingxuan Wu . Development of site-selective photo crosslinking between tyrosine and sulfonium in methyllysine readers. Chinese Chemical Letters, 2025, 36(10): 110756-. doi: 10.1016/j.cclet.2024.110756
13. [13]
  Xiaoli Deng , Xiangchao Lu , Yang Cao , Qianjin Chen . Electrochemical imaging uncovers the heterogeneity of HER activity by sulfur vacancies in molybdenum disulfide monolayer. Chinese Chemical Letters, 2025, 36(3): 110379-. doi: 10.1016/j.cclet.2024.110379
14. [14]
  Huamei Zhang , Jingjing Liu , Mingyue Li , Shida Ma , Xucong Zhou , Aixia Meng , Weina Han , Jin Zhou . Imaging polarity changes in pneumonia and lung cancer using a lipid droplet-targeted near-infrared fluorescent probe. Chinese Chemical Letters, 2024, 35(12): 110020-. doi: 10.1016/j.cclet.2024.110020
15. [15]
  Baoli Yin , Xinlin Liu , Zhe Li , Zhifei Ye , Youjuan Wang , Xia Yin , Sulai Liu , Guosheng Song , Shuangyan Huan , Xiao-Bing Zhang . Ratiometric NIR-Ⅱ fluorescent organic nanoprobe for imaging and monitoring tumor-activated photodynamic therapy. Chinese Chemical Letters, 2025, 36(5): 110119-. doi: 10.1016/j.cclet.2024.110119
16. [16]
  Meng Gao , Jiqiu Yin , XianChao Jia , Ye Gao , Yang Jiao . On-target site enriching fluorescent bioprobe for imaging of receptor tyrosine kinase in tumor. Chinese Chemical Letters, 2025, 36(6): 110297-. doi: 10.1016/j.cclet.2024.110297
17. [17]
  Xianghan Zhang , Yuan Qin , Huaicong Zhang , Yutian Cao , Haixing Zhu , Yingdi Tang , Zimeng Ma , Zehua Li , Jialin Zhou , Qunyan Dong , Peng Yang , Yuqiong Xia , Zhongliang Wang . An aggregation-independent and rotor-specific TPE-cyanine probe for in vivo near-infrared fluorescent imaging. Chinese Chemical Letters, 2025, 36(9): 110715-. doi: 10.1016/j.cclet.2024.110715
18. [18]
  Qingyuan Guo , Aojie Liu , Yinghui Huang , Jiayu Ding , Junjie Ding , Limin Wang , Yang Ding , Bo Peng , Lin Li , Bin Fang , Shan Jiang , Hua Bai . Small-molecule fluorescent probes for imaging and diagnosing ischemia-reperfusion injury. Chinese Chemical Letters, 2025, 36(12): 110943-. doi: 10.1016/j.cclet.2025.110943
19. [19]
  Mengxing Liu , Jing Liu , Hongxing Zhang , Jianan Tao , Peiwen Fan , Xin Lv , Wei Guo . One-pot accessing of meso–aryl heptamethine indocyanine NIR fluorophores and potential application in developing dye-antibody conjugate for imaging tumor. Chinese Chemical Letters, 2025, 36(4): 109994-. doi: 10.1016/j.cclet.2024.109994
20. [20]
  Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1232)
HTML views(15)

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