Citation: Xian-Tao JIANG, Xiao-Hui WANG, Pei-Yuan LI, Wei SU. Synthesis, Structure and Photoactivated Anticancer Activity of Ruthenium-Arene Complexes with Curcuminoids[J]. Chinese Journal of Inorganic Chemistry, ;2021, 37(3): 431-436. doi: 10.11862/CJIC.2021.047 shu

Synthesis, Structure and Photoactivated Anticancer Activity of Ruthenium-Arene Complexes with Curcuminoids

1.
Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001, China
2.
College of Pharmacy, Guangxi University of Chinese Medicine, Nanning 530001, China

Corresponding author: Pei-Yuan LI, lipearpear@163.com Wei SU, suwmail@163.com
Received Date: 15 June 2020
Revised Date: 1 November 2020

Figures(5)

Three ruthenium-arene complexes with curcuminoids (1~3) were synthesized through the reaction of[(η⁶-p-cymene)RuCl₂]₂ and the corresponding curcuminoids derivative (L¹~L³) followed by the reaction with 1, 3, 5-tiaza-7-phosphaadamantane (PTA). The complexes were structurally characterized by single crystal XRD, ¹H NMR, MS and elemental analysis. The inhibitory activities of the complexes towards HepG2 human liver cancer cell lines were investigated by MTT with light (λ>400 nm). The results show that three complexes present half-sandwich structure. Anticancer activity of the complexes was significantly improved by light, among which the IC₅₀ of complex 3 decreased from (60.3±1.1) μmol·L^-1 to (45.0±6.1) μmol·L^-1 against HepG2, indicating that light can effectively improve the anticancer activity of this kind of complexes. CCDC: 1514601, 1; 1514600, 2; 1514603, 3.
- ruthenium-arene complexes,
- curcuminoids,
- anticancer activity,
- crystal structure
1. [1]
  Murray B S, Babak M V, C G Hartinger, Dyson P. Coord. Chem. Rev., 2016, 306: 86-114 doi: 10.1016/j.ccr.2015.06.014
2. [2]
  Furrer J, Süss-Fink G. Coord. Chem. Rev., 2016, 309: 36-50 doi: 10.1016/j.ccr.2015.10.007
3. [3]
  ZHAO Y C, LI J, ZHANG P P, LIU S X, WEI D N, SU Z, QIAN Y, WANG F L, Sadler P J, LIU H K. Chem. J. Chinese Universities, 2019, 40(1): 30-40
4. [4]
  Thompson D S, Weiss G J, Jones S F, Burris H A, Ramanathan R K, Infante J R, Ogden A, von Hoff D D. J. Clin. Oncol., 2012, 30(S15): Abstr. 3033 doi: 10.1200/jco.2012.30.15_suppl.3033
5. [5]
  Kubanik M, Kandioller W, Kim K W, Anderson R F, Klapproth E, Jakupec M A, Roller A, Söhnel T, Keppler B K, Hartinger C G. Dalton Trans., 2016, 45: 13091-13103 doi: 10.1039/C6DT01110A
6. [6]
  Trondl R, Heffeter P, Kowol C R, Jakupec M A, Berger W, Keppler B K. Chem. Sci., 2014, 5: 2925-2932 doi: 10.1039/C3SC53243G
7. [7]
  Morris R E, Aird R E, Socorro P S, Chen H M, Cummings J, Hughes N D, Parsons S, Parkin A, Boyd G, Jodrell D I, Sadler P J. J. Med. Chem., 2001, 44: 3616-3621 doi: 10.1021/jm010051m
8. [8]
  Chen H M, Parkinson J A, Parsons S, Coxall R A, Gould R O, Sadler P J. J. Am. Chem. Soc., 2002, 124(12): 3064-3082 doi: 10.1021/ja017482e
9. [9]
  Scolaro C, Bergamo A, Brescacin L, Delfino R, Cocchietto M, Laurenczy G, Geldbach T J, Sava G, Dyson P J. J. Med. Chem., 2005, 48: 4161-4171 doi: 10.1021/jm050015d
10. [10]
  Chatterjee S, Kundu S, Bhattacharyya A, Hartinger C G, Dyson P J. J. Biol. Inorg. Chem., 2008, 13: 1149-1155 doi: 10.1007/s00775-008-0400-9
11. [11]
  Batchelor L K, Paunescu E, Soudani M, Scopelliti R, Dyson P J. Inorg. Chem., 2017, 56(16): 9617-9633 doi: 10.1021/acs.inorgchem.7b01082
12. [12]
  Ma L L, Ma R, Wang Z G, Yiu S M, Zhu G Y. Chem. Commun., 2016, 52(71): 10735-10738 doi: 10.1039/C6CC04354B
13. [13]
  Prior T J, Savoie H, Boyle R W, Murray B S. Organometallics, 2018, 37(3): 294-297 doi: 10.1021/acs.organomet.7b00868
14. [14]
  Caruso F, Pettinari R, Rossi M, Monti E, Gariboldi M B, Marchetti F, Pettinari C, Caruso A, Ramani M V, Subbaraju G V. J. Inorg. Biochem., 2016, 162: 44-51 doi: 10.1016/j.jinorgbio.2016.06.002
15. [15]
  Ma L L, Lin X D, Li C, Xu Z F, Chan C Y, Tse M K, Shi P, Zhu G Y. Inorg. Chem., 2018, 57(5): 2917-2924 doi: 10.1021/acs.inorgchem.8b00053
16. [16]
  Paunescu E, Soudani M, Martin P, Scopelliti R, Bello M L, Dyson P J. Organometallics, 2017, 36(17): 3313-3321 doi: 10.1021/acs.organomet.7b00468
17. [17]
  Lei X L, Su W, Li P Y, Xiao Q, Huang S, Qian Q Q, Huang C S, Qian D N, Lan H X. Polyhedron, 2014, 81: 614-618 doi: 10.1016/j.poly.2014.07.019
18. [18]
  Caruso F, Rossi M, Benson A, Opazo C, Freedman D, Monti E, Gariboldi M B, Shaulky J, Marchetti F, Pettinari R. J. Med. Chem., 2012, 55: 1072-1081 doi: 10.1021/jm200912j
19. [19]
  Pettinari R, Pettinari C, Mahetti F, Clavel C M, Scopelliti R, Dyson P J. Organometallics, 2014, 33(14): 3709-3715 doi: 10.1021/om500317b
20. [20]
  Banerjee S, Chakravarty A R. Acc. Chem. Res., 2015, 48: 2075-2083 doi: 10.1021/acs.accounts.5b00127
21. [21]
  Zhang J F, Liang Y C, Lin X D, Zhu X Y, Yan L, Li S L, Yang X, Zhu G Y, Rogach A L, Yu P K N, Shi P, Tu L C, Chang C C, Zhang X H, Chen Z F, Zhang W J, Lee C S. ACS Nano, 2015, 9: 9741-9756 doi: 10.1021/acsnano.5b02513
22. [22]
  Mitra K, Gautam S, Kondaiah P, Chakravarty A R. Angew. Chem. Int. Ed., 2015, 54: 13989-13993 doi: 10.1002/anie.201507281
23. [23]
  Renfrew A K, Bryce N S, Hambley T. Chem. Eur. J., 2015, 21: 1522415234 doi: 10.1002/chem.201502702
24. [24]
  Li P Y, Su W, Lei X L, Xiao Q, Huang S. Appl Organometal Chem., 2017, 31: e3685 doi: 10.1002/aoc.3685
25. [25]
  Sheldrick G M. Acta Crystallogr. Sect. C, 2015, 71: 3-8 doi: 10.1107/S2053229614024218
26. [26]
  Sheldrick G M. Acta Crystallogr. Sect. A, 2008, 64: 112-122 doi: 10.1107/S0108767307043930
27. [27]
  Su W, Zhou Q, Huang Y M, Huang Q Y, Huo L N, Xiao Q, Huang S, Huang C S, Chen R, Qian Q Q, Liu L F, Li P Y. Appl. Organometal Chem., 2013, 27: 307-312 doi: 10.1002/aoc.2977
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沈阳化工大学材料科学与工程学院沈阳 110142