Synthesis and Antitumor Properties of Ruthenium-Arene Complexes Based on Natural Product Perillol
- Corresponding author: XUE Xu-Ling, xuexuling87@163.com LIU Hong-Ke, liuhongke@njnu.edu.cn
Citation: WU Jian, TAO Qin, GE Chao, XUE Xu-Ling, QIAN Yong, LIU Hong-Ke. Synthesis and Antitumor Properties of Ruthenium-Arene Complexes Based on Natural Product Perillol[J]. Chinese Journal of Inorganic Chemistry, ;2020, 36(7): 1223-1232. doi: 10.11862/CJIC.2020.159
Takahara P M, Rosenzweig A C, Frederick C A, et al. Nature, 1995, 377(6550):649-652
doi: 10.1038/377649a0
Wang Z G, Wang N, Cheng S C, et al. Chem-US, 2019, 5:3151 -3165
Xue X L, Qian C G, Fang F B, et al. Angew. Chem. Int. Ed., 2019, 58(36):12661-12666
doi: 10.1002/anie.201906203
Rabik C A, Dolan M E. Cancer Treat. Rev., 2007, 33(1):9-23
doi: 10.1016/j.ctrv.2006.09.006
Liu Z, Sadler P J. Acc. Chem. Res., 2014, 45:1174-1185
Zaki M, Hairat S, Aazam E S. RSC Adv., 2019, 9:3239-3278
doi: 10.1039/C8RA07926A
Zeng L L, Gupta P, Chen Y L, et al. Chem. Soc. Rev., 2017, 46:5771-5804
doi: 10.1039/C7CS00195A
Li J J, Guo L H, Tian Z Z, et al. Inorg. Chem., 2018, 57(21): 13552-13563
doi: 10.1021/acs.inorgchem.8b02161
Liu H K, Sadler P J. Acc. Chem. Res., 2011, 44(5):349-359
doi: 10.1021/ar100140e
Novohradsky V, Rovira A, Hally C, et al. Angew. Chem. Int.Ed., 2019, 58(19):6311-6315
doi: 10.1002/anie.201901268
Needham R J, Sanchez-Cano C, Zhang X. Angew. Chem. Int. Ed., 2017, 56(4):1017-1020
doi: 10.1002/anie.201610290
Imberti C, Zhang P Y, Huang H Y, et al. Angew. Chem. Int. Ed., 2019, 131:2-15
doi: 10.1002/ange.201813331
Kilpin K J, Cammack S M, Clavel C M, et al. Dalton Trans., 2013, 42:2008-2014
doi: 10.1039/C2DT32333H
Albada B, Metzler-Nolte N. Chem. Rev., 2016, 116(19):11797 -11839
doi: 10.1021/acs.chemrev.6b00166
Hao L, Li Z W, Zhang D Y, et al. Chem. Sci., 2019, 10:1285- 1293
doi: 10.1039/C8SC04242J
He L, Liao S Y, Tan C P, et al. Chem. Eur. J., 2013, 19(36):12152-12160
doi: 10.1002/chem.201301389
Zeng W, Zhao Y, Luo Q, et al. Sci. China Chem., 2016, 59:1240-1249
doi: 10.1007/s11426-016-0178-7
Kong Y Q, Chen F, Su Z, et al. J. Inorg. Biochem., 2018, 182:194-199
doi: 10.1016/j.jinorgbio.2018.02.004
Mitra K, Gautam S, Kondaiah P, et al. Angew. Chem. Int. Ed., 2015, 54(47):13989-13993
doi: 10.1002/anie.201507281
Wulff J E, Siegrist R, , Myers A G. J. Am. Chem. Soc., 2007, 129(46):14444-14451
doi: 10.1021/ja075327f
Bailey H H, Attia S, Love R R, et al. Cancer Chemother. Pharmcol., 2008, 62:149-157
doi: 10.1007/s00280-007-0585-6
Meadows S M, Mulkerin D, Berlin J, et al. Int. J. Gastroin- test. Cancer, 2002, 32:125-128
doi: 10.1385/IJGC:32:2-3:125
Yuri T, Danbara N, Tsujita-Kyutoku M, et al. Breast Cancer Res. Treat., 2004, 84(3):251-260
doi: 10.1023/B:BREA.0000019966.97011.4d
Hui Z, Zhang M H, Cong L, et al. Molecules, 2014, 19(5):6671-6682
doi: 10.3390/molecules19056671
Sarkar S, Azab B, Quinn B A, et al. Curr. Mol. Med., 2014, 14(1):124-140
Loutrari H, Hatziapostolou M, Skouridou V, et al. J. Pharma- col. Exp. Ther., 2004, 311(2):568-575
doi: 10.1124/jpet.104.070516
Furrer J, Süss-Fink G. Coord. Chem. Rev., 2016, 309:36-50
doi: 10.1016/j.ccr.2015.10.007
Wu Q, Liu L Y, Li S L, et al. J. Inorg. Biochem., 2018, 189:30-39
doi: 10.1016/j.jinorgbio.2018.08.013
Mohamadi M, Hassankhani A, Ebrahimipour S Y, et al. Int. J. Biol. Macromol., 2017, 94:85-95
doi: 10.1016/j.ijbiomac.2016.09.113
Chen T C, Fonseca C O D, Schönthal A H. Am. J. Cancer. Res., 2015, 5(5):1580-1593
Kubeil M, Vernooij R R, Kubeil C, et al. J. Inorg. Chem., 2017, 56(10):5941-5952
doi: 10.1021/acs.inorgchem.7b00599
Kandioller W, Hartinger C G, Nazarov A A, et al. Organome- tallics, 2009, 28(15):4249-4251
doi: 10.1021/om900483t
Tang J H, Sun Y, Gong Z L, et al. J. Am. Chem. Soc., 2018, 140(24):7723-7729
doi: 10.1021/jacs.8b04452
Kepert C M, Deacon G B, Sahely N, et al. Inorg. Chem., 2004, 43(9):2818-2827
doi: 10.1021/ic0351895
Göttle A J, Alary F, Boggio - Pasqua M, et al. Inorg. Chem., 2016, 55(9):4448-4456
doi: 10.1021/acs.inorgchem.6b00268
Scott R L. Recl. Trav. Chim. Pays-Bas, 1956, 75:787-789
Liu Z C, Wang B D, Li B, et al. Eur. J. Med. Chem., 2010, 45(11):5353-5361
doi: 10.1016/j.ejmech.2010.08.060
Zhu H B, Wang L, Chen Y M, et al. RSC Adv., 2014, 4:29917 -29924
doi: 10.1039/C4RA03793F
Meier S M, Kreutz S D, Winter L, et al. Angew. Chem. Int. Ed., 2017, 56(28):8267-8271
doi: 10.1002/anie.201702242
Wang Y Q, Wang X Q, Wang J, et al. Inorg. Chem., 2011, 50 (24):12661-12668
doi: 10.1021/ic201712e
Mohanraj M, Ayyannan G, Raja G, et al. Mater. Sci. Eng. C, 2016, 69:1297-1306
doi: 10.1016/j.msec.2016.08.043
Pacheco M E, Bruzzone L J. J. Lumin., 2013, 137:138-142
doi: 10.1016/j.jlumin.2012.12.056
Galluzzi L, Senovilla L, Vitale I, et al. Oncogene, 2012, 31:1869-1883
doi: 10.1038/onc.2011.384
Wang Y R, Feng L, Xu L, et al. Sens. Actuators B, 2017, 245:923-931
doi: 10.1016/j.snb.2017.02.046
Li H D, Yao Q C, Fan J L, et al. Dyes Pigm., 2016, 133:79-85
doi: 10.1016/j.dyepig.2016.05.039
Reja S I, Khan I A, Bhalla V, et al. Chem. Commun., 2016, 52(6):1182-1185
doi: 10.1039/C5CC08217J
Rastegari B, Karbalaei-Heidari H R, Yousefi R, et al. Bioorg. Med. Chem., 2016, 24(7):1504-1512
doi: 10.1016/j.bmc.2016.02.020
Liu Z, Salassa L, Habtemariam A, et al. Inorg. Chem., 2011, 50(12):4022-4027
Chaudhary S C, Alam M S, Siddiqui M S, et al. Chem. Biol. Interact., 2009, 179:145-153
doi: 10.1016/j.cbi.2008.12.016
Xiao H B, Zhang W, Li P, et al. Angew. Chem. Int. Ed., 2019, 58:2-17
doi: 10.1002/anie.201813331
Huang H Y, Zhang P Y, Yu B L, et al. J. Med. Chem., 2014, 57(21):8971-8983
doi: 10.1021/jm501095r
Doll S, Freitas F P, Shah R, et al. Nature, 2019, 10:1-7
Sampath S, Subramani S, Janardhanam S, et al. Phytomedi-cine, 2018, 46:57-68
doi: 10.1016/j.phymed.2018.04.007
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Inset:fitted curve of ln(C/C0) of the complex at 314 nm versus time; C0, Ru-L=50 μmol·L-1
Inset: fitted curve of CDNA/(εa-εf) of the complex at 314 nm versus concentration; CRu-L=30 μmol·L-1, CCT-DNA=0~40 μmol·L-1, CRu-L/CCT-DNA=0~1.3
CBSA=3 μmol·L-1, CRu-L=0~20 μmol·L-1, CBSA/CRu-L=0~6.6
CHSA=1 μmol·L-1, CRu-L=0~5 μmol·L-1, CHSA/CRu-L=0~5