Citation: SHI Lei, JIANG Huan-Feng, YIN Wei, WANG Hua-Hua, WANG Hui, ZHANG Lei, JI Liang-Nian, LIU Hai-Yang. Synthesis, Fluorescence and DNA Photocleavage Activity of Phenothiazine-Corrole Gallium(III) Complexes[J]. Acta Physico-Chimica Sinica, ;2012, 28(02): 465-469. doi: 10.3866/PKU.WHXB201111291 shu

Synthesis, Fluorescence and DNA Photocleavage Activity of Phenothiazine-Corrole Gallium(III) Complexes

SHI Lei ^1,2, ,
JIANG Huan-Feng ² ,
YIN Wei ¹ ,
WANG Hua-Hua ² ,
WANG Hui ³ ,
ZHANG Lei ² ,
JI Liang-Nian ³ ,
LIU Hai-Yang ^2,

1.
1. Department of Chemistry, Guangdong University of Education, Guangzhou 510303, P. R. China;
2. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, P. R. China;
3. State Key Laboratory of Optoelectronics Materials and Technologies, Sun Yat-Sen University, Guangzhou 510275, P. R. China

Received Date: 13 October 2011
Available Online: 29 November 2011
Fund Project: 国家自然科学基金(20971046, 21171057, 61178037, 11004256) (20971046, 21171057, 61178037, 11004256) 广东省自然科学基金(10351064101000000) (10351064101000000) 光电材料与技术国家重点实验室(中山大学)开放基金及广东第二师范学院教授博士科研专项经费研究项目(10ARF14)资助 (中山大学)开放基金及广东第二师范学院教授博士科研专项经费研究项目(10ARF14)

Phenothiazine (PTZ)-corrole dyads 1-3 and their gallium(III) complexes 4-6 have been synthesized and characterized. The steady-state absorption and emission spectra and the time-resolved fluorescence decay profiles have been measured in toluene. The radiative and nonradiative rate constants have been obtained from the fluorescence quantum yields and monoexponential fluorescence lifetimes. The absorption spectra revealed that the gallium(III) corrole dyads exhibit stronger Soret bands and Q bands than free base corrole dyads. The fluorescence quantum yields of 1-3 are 0.156, 0.134, and 0.139, and the radiative rate constants are 4.02×10⁷, 3.47×10⁷, and 2.89×10⁷ s^-1, respectively. The fluorescence quantum yields of 4-6 are 0.502, 0.443, and 0.494, and the radiative rate constants are 20.9×10⁷, 16.78×10⁷, and 21.11×10⁷ s^-1, which are obviously higher than those of the corresponding free base corroles. The lifetimes of 4-6 are 2.40, 2.64, and 2.34 ns, respectively, which are somewhat shorter than those of the corresponding free base corroles. Agarose gel electrophoresis shows that these gallium(III) corrole dyads could cleave supercoiled DNA (form I) to give nicked-circular DNA (form II) under irradiation.
- Corrole,
- Phenothiazine,
- Gallium(III),
- Fluorescence,
- DNA
1. [1]
  (1) Fang, H. F.; Ling, Z.; Brothers, J. P.; Fu, X. F. Chem. Commun. 2011, 47, 11677.
2. [2]
  (2) Nigel-Etinger, I.; Mahammed, A.; Gross, Z. Catal. Sci. Technology 2011, 1 (4), 578.
3. [3]
  (3) Zhai, Q. Q.; Xu, L.; Ge, Y. S.; Tian, T.;Wu,W. D.; Yan, S. Y.; Zhou, Y. Y.; Deng, M. G.; Liu, Y.; Zhou, X. Chem. Eur. J. 2011, 17 (32), 8890.
4. [4]
  (4) Aviv, I.; Gross, Z. Chem. Commun. 2007, 1987 and references therein.
5. [5]
  (5) Liu, H. Y.; Yam, F.; Xie, Y. T.; Li, X. Y.; Chang, C. K. J. Am. Chem. Soc. 2009, 131, 12890.
6. [6]
  (6) Flamigni, L.; Gryko, D. T. Chem. Soc. Rev. 2009, 38, 1635.
7. [7]
  (7) Botoshansky, M.; Palmer, J. H.; Durrell, A. C.; Gray, H. B.; Gross, Z. J. Am. Chem. Soc. 2011, 133 (33), 12899.
8. [8]
  (8) Tasior, M.; Gryko, D. T.; Cembor, M.; Jaworski, J. S.; Venturac B.; Flamigni L. New J. Chem. 2007, 31, 247.
9. [9]
  (9) Tasior, M.; Gryko, D. T.; Shen, J.; Kadish, K. M.; Becherer, T.; Venturac, B.; Flamigni, L. J. Phys. Chem. C 2008, 112, 19699.
10. [10]
  (10) He, C. L.; Ren, F. L.; Zhang, X. B.; Han, Z. X. Talanta 2006, 70, 364.
11. [11]
  (11) Ghosh, A.; Jynge, K. Chem. Eur. J. 1997, 3, 823.
12. [12]
  (12) Simkhovich, L.; ldberg, I.; Gross, Z. J. Inorg. Biochem. 2000, 80 (3-4), 235.
13. [13]
  (13) Bendix, J.; Dmochowski, I. J.; Gray, H. B.; Mahammed, A.; Simkhovich, L.; Gross, Z. Angew. Chem. Int. Edit. 2000, 39 (22), 4048.
14. [14]
  (14) Liu, X.; Mahammed, A.; Tripathy, U.; Gross, Z.; Steer, R. P. Chem. Phys. Lett. 2008, 459 (1-6), 113.
15. [15]
  (15) Saltsman, I.; Mahammed, A.; ldberg, I.; Tkachenko, E.; Botoshansky, M.; Gross, Z. J. Am. Chem. Soc. 2002, 124 (25), 7411.
16. [16]
  (16) Sorasaenee, K.; Taqavi, P.; Henling, L. M.; Gray, H. B.; Tkachenko, E.; Mahammed, A.; Gross, Z. J. Porphyr. Phthalocyanines 2007, 11 (3-4), 189.
17. [17]
  (17) Mahammed, A.; Gray, H. B.;Weaver, J. J.; Sorasaenee, K.; Gross, Z. Bioconjugate Chem. 2004, 15 (4), 738.
18. [18]
  (18) Agadjanian, H.; Ma, J.; Rentsendorj, A.; Valluripalli, V.; Hwang, J. Y.; Mahammed, A.; Farkas, D. L.; Gray, H. B.; Gross, Z.; Medina-Kauwe, L. K. Proc. Nat. Acad. Sci. U. S. A. 2009, 106 (15), 6105.
19. [19]
  (19) Motohashi, N. Antitumor Activities of Phenothiaiznes. In Phenothiazines and 1,4-Benzothiazines. Chemical and Biological Aspects. Bioactive Molecules. Gupta, R. R. Ed.; Elsevier: Amsterdam, 1988; Vol. 4, pp 705-770.
20. [20]
  (20) Viola, G.; Dall'Acqua, F. Current Drug Targets 2006, 7, 1135.
21. [21]
  (21) Shi, L.; Liu, H. Y.; Peng, K. M.;Wang, X. L.; You, L. L.; Zhang, L.;Wang, H.; Ji, L. N.; Jiang, H. F. Tetrahedron Lett. 2010, 51, 3439.
22. [22]
  (22) Adler, A. D.; Lon , F. R.; Finarelli, J. D.; ldmacher, J.; Assour, J.; Korsakoff, L. J. Org. Chem. 1967, 32 (2), 476.
23. [23]
  (23) Ghosh, A.;Wondimagegn, T.; Parusel, A. B. J. J. Am. Chem. Soc. 2000, 122, 5100.
24. [24]
  (24) Peng, K. M.; Shao,W. L.;Wang, H. H.; Ying, X.;Wang, H.; Ji, L. N.; Liu, H. Y. Acta Phys. -Chim. Sin. 2011, 27, 199. [彭开美, 邵文莉, 汪华华, 应晓, 王惠, 计亮年, 刘海洋. 物理化学学报, 2011, 27, 199.]
25. [25]
  (25) Gross, Z.; Galili, N.; Simkhovich, L.; Saltsman, I.; Botoshansky, M.; Bläser, D.; Boese, R.; ldberg, I. Org. Lett. 1999, 1, 599.
26. [26]
  (26) Kowalska, D.; Liu, X.; Tripathy, U.; Mahammed, A.; Gross, Z.; Hirayama, S.; Steer, R. P. Inorg. Chem. 2009, 48 (6), 2670.
1. [1]
  Aijia Tang , Xinze Li , Yaning Shi , Xueen Fang . 玩“转”芯片，让DNA看得见. University Chemistry, 2026, 41(8): 276-285. doi: 10.12461/PKU.DXHX202507111
2. [2]
  Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
3. [3]
  Xingyu Liu , Tong Li , Fangfang Chen , Fen Ma . DNA分子的“生命编程”：从复制密码到体外应用. University Chemistry, 2026, 41(8): 286-291. doi: 10.12461/PKU.DXHX202507114
4. [4]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
5. [5]
  Feng Lu , Tao Wang , Qi Wang . Preparation and Characterization of Water-Soluble Silver Nanoclusters: A New Design and Teaching Practice in Materials Chemistry Experiment. University Chemistry, 2025, 40(4): 375-381. doi: 10.12461/PKU.DXHX202406005
6. [6]
  Hao YAN , Meng WANG , Chenyi HU , Ming LI , Chuanjun YUAN . Synthesis of europium complex bonded NaYF₄∶Yb, Er micron-materials and their applications in dual-mode fluorescent development of latent fingerprints. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 991-1002. doi: 10.11862/CJIC.20250302
7. [7]
  Yingyue ZHANG , Liuqing KANG , Yating YANG , Xiaofen GUAN , Wenmin WANG . Crystal structure and antibacterial activity of two Gd₂ complexes based on polydentate Schiff-base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1867-1877. doi: 10.11862/CJIC.20250100
8. [8]
  YanYuan Jia , Rong Rong , Jie Liu , Jing Guo , GuoYu Jiang , Shuo Guo . Unity is Strength, and Independence Shines: A Science Popularization Experiment on AIE and ACQ Effects. University Chemistry, 2024, 39(9): 349-358. doi: 10.12461/PKU.DXHX202402035
9. [9]
  Qin Li , Kexin Yang , Qinglin Yang , Xiangjin Zhu , Xiaole Han , Tao Huang . Illuminating Chlorophyll: Innovative Chemistry Popularization Experiment. University Chemistry, 2024, 39(9): 359-368. doi: 10.3866/PKU.DXHX202309059
10. [10]
  Zehua Zhang , Haitao Yu , Yanyu Qi . Design Strategy for Thermally Activated Delayed Fluorescence Materials with Multiple Resonance Effect. Acta Physico-Chimica Sinica, 2025, 41(1): 100006-0. doi: 10.3866/PKU.WHXB202309042
11. [11]
  Wenwei Zeng , Qingyu Sun , Mengxiang Liang , Lirong Lin , Laiying Zhang . Unveiling Anti-Counterfeiting Secrets: Excitation-Dependent Luminescence in Sb³⁺-Doped Perovskite Materials. University Chemistry, 2026, 41(2): 375-384. doi: 10.12461/PKU.DXHX202503036
12. [12]
  Chen LU , Qinlong HONG , Haixia ZHANG , Jian ZHANG . Syntheses, structures, and properties of copper-iodine cluster-based boron imidazolate framework materials. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 149-154. doi: 10.11862/CJIC.20240407
13. [13]
  Shuwen SUN , Gaofeng WANG . Two cadmium coordination polymers constructed by varying Ⅴ-shaped co-ligands: Syntheses, structures, and fluorescence properties. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 613-620. doi: 10.11862/CJIC.20230368
14. [14]
  Dongdong YANG , Jianhua XUE , Yuanyu YANG , Meixia WU , Yujia BAI , Zongxuan WANG , Qi MA . Design and synthesis of two coordination polymers for the rapid detection of ciprofloxacin based on triphenylpolycarboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2466-2474. doi: 10.11862/CJIC.20240266
15. [15]
  Jiming XI , Yukang TENG , Rui ZHANG , Zhenzhong LU . Fluorescent coordination polymers based on anthracene-and pyrene-derivative ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 847-854. doi: 10.11862/CJIC.20240367
16. [16]
  Yuanyu YANG , Jianhua XUE , Yujia BAI , Lulu CUI , Dongdong YANG , Qi MA . Design, synthesis, and detection of Al³⁺ of two zinc complexes based on Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1207-1216. doi: 10.11862/CJIC.20250005
17. [17]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
18. [18]
  Youbo HU , Donggang LI , Changhua SUN , Zhenzhong LU , Songjun GU . Coordination polymers based on anthracene- and pyrene-derived ligands: Crystal structure, fluorescent property, and framework isomerization. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1681-1688. doi: 10.11862/CJIC.20250004
19. [19]
  Gaofeng WANG , Shuwen SUN , Lixin Meng , Dequn PENG . Syntheses and fluorescent sensing properties of two coordination polymers based on 9, 9′-dihexyl-2, 7-di(pyridin-4-yl)fluorene. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 331-339. doi: 10.11862/CJIC.20250260
20. [20]
  Pengfei Li , Chulin Qu , Fan Wu , Hu Gao , Chengyan Zhao , Yue Zhao , Zhen Shen . Robust free-base and metalated corrole radicals with reduction-induced emission. Chinese Chemical Letters, 2025, 36(2): 110292-. doi: 10.1016/j.cclet.2024.110292

Get Citation

PDF

XML

Metrics

PDF Downloads(842)
Abstract views(3039)
HTML views(50)

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