Abstract
Six new lanthanide(III) complexes, namely [GdIII(QL1)3(BL1)] (Gd1), [GdIII(QL1)3(BL2)] (Gd2), [LuIII(QL2)2(BL3)(NO3)] (Lu1), [LuIII(QL2)2(BL2)(NO3)] (Lu2), [YbIII(QL3)2(BL2)(NO3)] (Yb1), and [YbIII(QL4)2(BL2)(NO3)] (Yb2) coordinated with 5,7-dibromo-8-quinolinol (H-QL1), 5,5′-dimethyl-2,2′-bipyridyl (BL1), 4,4′-di-tert-butyl-2,2′-bipyridine (BL2), 5,7-dibromo-2-methylquinolin-8-ol (H-QL2), 2,2′-bipyridine (BL3), 5,7-dichloro-8-hydroxyquinoline (H-QL3), and 5,7-dichloro-8-hydroxy-2-methylquinoline (H-QL4), were prepared. The LnIII complexes Gd1, Gd2, Lu1, Lu2, Yb1 and Yb2 showed high cytotoxicity toward cervical (HeLa), ovarian (SK-OV-3) and lung (NCI-H460) cancer cells with IC50 values from 0.18 ± 0.14 to 8.02 ± 1.71 μM. In addition, Yb1 and Yb2 impaired mitochondrial functions, decreased mitochondrial membrane potential, and altered the levels of mitochondrial related-proteins. The apoptosis-inducing capability was in the order of Yb2 > Yb1. Such observed differences in biological activities could be caused by the electronic effect of the methyl group of H-QL4 in Yb2.
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Gandioso A, Shaili E, Massaguer A, Artigas G, González-Cantó A, Woods JA, Sadler PJ, Marchán V (2015) Chem Commun 51:9169–9172
Zeng L, Gupta P, Chen Y, Wang E, Ji L, Chao H, Chen ZS (2017) Chem Soc Rev 46:5771–5804
Qin QP, Zou BQ, Wang ZF, Huang XL, Zhang Y, Tan MX, Wang SL, Liang H (2019) Eur J Med Chem 183:111727. https://doi.org/10.1016/j.ejmech.2019.111727
Ni WX, Man WL, Cheung MTW, Sun RWY, Shu YL, Lam YW, Che CM, Lau TC (2011) Chem Commun 47:2140–2142
Fang L, Qin X, Zhao J, Gou S (2019) Inorg Chem 58:2191–2200
Qin QP, Wang ZF, Huang XL, Tan MX, Luo ZH, Wang SL, Zou BQ, Liang H (2019) Dalton Trans 48:15247–15254
Cao JJ, Zheng Y, Wu XW, Tan CP, Chen MH, Wu N, Ji LN, Mao ZW (2019) J Med Chem 62:3311–3322
Liu Z, Sadler PJ (2014) Acc Chem Res 47:1174–1185
Thota S, Rodrigues DA, Crans DC, Barreiro EJ (2018) J Med Chem 61:5805–5821
Dasari S, Singh S, Kumar P, Sivakumar S, Patra AK (2019) Eur J Med Chem 163:546–559
Qin QP, Wang ZF, Tan MX, Huang XL, Zou HH, Zou BQ, Shi BB, Zhang SH (2019) Metallomics 11:1005–1015
Meng T, Qin QP, Chen ZL, Zou HH, Wang K, Liang FP (2019) Eur J Med Chem 169:103–110
Kostova I (2005) Curr Med Chem Anti-Cancer Agents 5:591–602
Kostova I, Manolov I, Momekov G, Tzanova T, Konstantinov S (2005) Karaivanova. Eur J Med Chem 40:1246–1254
Kostova I, Manolov I, Momekov G (2004) Eur J Med Chem 39:765–775
Kostova I, Momekov G (2008) Eur J Med Chem 43:178–188
Li Y, Yang ZY, Wang MF (2009) Eur J Med Chem 44:4585–4595
Hussain A, Gadadhar S, Goswami TK, Karande AA, Chakravarty AR (2012) Eur J Med Chem 50:319–331
Lim LMP, Delgado R, Marques F, Gano L, Santos I (2010) Eur J Med Chem 45:5621–5627
Yang JW, Lin YL, Dong C, Zhou CQ, Chen JX, Wang B, Zhou ZZ, Sun B, Chen WH (2014) Eur J Med Chem 87:168–174
Ballico M, Rapozzi V, Xodo LE, Comuzzi C (2011) Eur J Med Chem 46:712–720
Deka B, Sarkar T, Banerjee S, Kumar A, Mukherjee S, Deka S, Saikia KK, Hussain A (2017) Dalton Trans 46:396–409
Havrylyuk D, Howerton BS, Nease L, Parkin S, Heidary DK, Glazer EC (2018) Eur J Med Chem 156:790–799
Jia X, Yang FF, Li J, Liu JY, Xue JP (2013) J Med Chem 56:5797–5805
Oliveri V, Viale M, Aiello C, Vecchio G (2015) J Inorg Biochem 142:101–108
Tang Q, Ni WX, Leung CF, Man WL, Lau KKK, Liang Y, Lam YW, Wong WY, Peng SM, Liu GJ, Lau TC (2013) Chem Commun 49:9980–9982
Santos CM, Cabrera S, Rios-Luci C, Padron JM, Solera IL, Quiroga AG, Medrano MA, Navarro-Ranninger C, Aleman J (2013) Dalton Trans 42:13343–13348
Correia I, Adao P, Roy S, Wahba M, Matos C, Maurya MR, Marques F, Pavan FR, Leite CQF, Avecilla F, Pessoa JC (2014) J Inorg Biochem 141:83–93
Tardito S, Barilli A, Bassanetti I, Tegoni M, Bussolati O, Franchi-Gazzola R, Mucchino C, Marchio L (2012) J Med Chem 55:10448–10459
Barilli A, Atzeri C, Bassanetti I, Ingoglia F, Dall’Asta V, Bussolati O, Maffini M, Mucchino C, Marchio L (2014) Mol Pharm 11:1151–1163
Yang L, Zhang J, Wang C, Qin X, Yu Q, Zhou Y, Liu J (2014) Metallomic 6:518–531
Gobec M, Kljun J, Sosic I, Mlinaric-Rascan I, Ursis M, Gobec S, Turel I (2014) Dalton Trans 43:9045–9051
Qin QP, Wang ZF, Huang XL, Tan MX, Zou BQ, Liang H (2019) Eur J Med Chem 184:111751. https://doi.org/10.1016/j.ejmech.2019.111751
Liu YC, Wei JH, Chen ZF, Liu M, Gu YQ, Huang KB, Li ZQ, Liang H (2013) Eur J Med Chem 69:554–563
Ferraz KSO, Reis DC, Da Silva JG, Souza-Fagundes EM, Baran EJ, Beraldo H (2013) Polyhedron 63:28–35
Zou HH, Meng T, Chen Q, Zhang YQ, Wang HL, Li B, Wang K, Chen ZL, Liang FP (2019) Inorg Chem 58:2286–2298
Meng T, Qin QP, Chen ZL, Zou HH, Wang K, Liang FP (2019) Dalton Trans 48:5352–5360
Filak LK, Kalinowski DS, Bauer TJ, Richardson DR, Arion VB (2014) Inorg Chem 53:6934–6943
Heidary DK, Howerton B, Glazer EC (2014) J Med Chem 57:8936–8946
Chen D, Cui QC, Yang H, Barrea RA, Sarkar FH, Sheng S, Yan B, Reddy GP, Dou QP (2007) Cancer Res 67:1636–1644
Qin QP, Chen ZF, Qin JL, He XJ, Li YL, Liu YC, Huang KB, Liang H (2015) Eur J Med Chem 92:302–313
Meng T, Qin QP, Zou HH, Wang K, Liang FP (2019) ACS Med Chem Lett 10:1603–1608
Liu YC, Chen ZF, Song XY, Peng Y, Qin QP, Liang H (2013) Eur J Med Chem 59:168–175
Chen ZF, Gu YQ, Song XY, Liu YC, Peng Y, Liang H (2013) Eur J Med Chem 59:194–202
Qin QP, Wang SL, Tan MX, Liu YC, Meng T, Zou BQ, Liang H (2019) Eur J Med Chem 161:334–342
Gothe Y, Marzo T, Messori L, Metzler-Nolte N (2016) Chem Eur J 22:1–9
Wang JQ, Zhang PY, Ji LN, Chao H (2015) J Inorg Biochem 146:89–96
Gothe Y, Marzo T, Messori L, Metzler-Nolte N (2016) Chem Eur J 22:12487–12494
Compain G, Oumata N, Clarhaut J, Péraudeau E, Renoux B, Galons H (2018) Eur J Med Chem 158:1–6
Spanò V, Pennati M, Parrino B, Carbone A, Montalbano A, Cilibrasi V, Zuco V, Lopergolo A, Cominetti D, Diana P, Cirrincione G, Barraja P, Zaffaroni N (2016) J Med Chem 59:157223–157238
Spanò V, Parrino B, Carbone A, Montalbano A, Salvador A, Brun P, Vedaldi D, Diana P, Cirrincione G, Barraja P (2015) Eur J Med Chem 102:334–351
Parrino B, Attanzio A, Spanò V, Cascioferro S, Montalbano A, Barraja P, Tesoriere L, Diana P, Cirrincione G, Carbone A (2017) Eur J Med Chem 138:371–383
Sheldrick GM (2008) A short history of SHELXL. Acta Crystallogr Sect A Found Crystallogr 64:112–122
Sheldrick GM (2015) Crystal structure refinement with SHELXL. Acta Crystallogr Sect C Struct Chem 71:3–8
Scaduto RC Jr, Grotyohann LW (1999) Biophys J 76:469–477
Huang GB, Chen S, Qin QP, Luo JR, Tan MX, Wang ZF, Zou BQ, Liang H (2019) New J Chem 43:8146–8152
Qin QP, Zou BQ, Tan MX, Wang SL, Liu YC, Liang H (2018) New J Chem 42:15479–15487
Cao R, Jia J, Ma X, Zhou M, Fei H (2013) J Med Chem 56:3636–3644
Fulda S, Debatin KM (2006) Oncogene 25:4798–4811
Tan C, Lai S, Wu S, Hu S, Zhou L, Chen Y, Wang M, Zhu Y, Lian W, Peng W, Ji LN, Xu A (2010) J Med Chem 53:7613–7624
Wang SL, Wang ZF, Qin QP, Tan MX, Luo DM, Zou BQ, Liu YC (2019) Inorg Chem Commun 99:77–81
Qin QP, Wang ZF, Tan MX, Wang SL, Zou BQ, Luo DM, Qin JL, Zhang SH (2019) Inorg Chem Commun 104:27–30
Qin QP, Zou BQ, Hu FL, Huang GB, Wang SL, Gu YQ, Tan MX (2018) Med Chem Commun 9:1639–1648
Chen ZF, Qin QP, Qin JL, Liu YC, Huang KB, Li YL, Meng T, Zhang GH, Peng Y, Luo XJ, Liang H (2015) J Med Chem 58:2159–2179
Qin QP, Wei ZZ, Wang ZF, Huang XL, Tan MX, Zou HH, Liang H (2020) Chem Commun 56:3999−4002
Acknowledgements
We thank the National Natural Science Foundation of China (Nos. 51963021, 21867017 and 21761033), the Natural Science Foundation of Guangxi (No. 2018GXNSFBA138021, 2018GXNSFBA281188 and 2017GXNSFBA19833), the PhD Research Startup Program of Yulin Normal University (No. G2019ZK14), the China University Students Innovative Project (201910606139), the Innovative Team & Outstanding Talent Program of Colleges and Universities in Guangxi (2017-38), the Basic Skills Improvement Project for the Young and Middle-aged Teachers in Guangxi Colleges and Universities (No. 2019KY1163) and the Innovative Team and Outstanding Talent Program of Colleges and Universities in Guangxi (2014-49 and 2017-38) for financial support.
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11243_2020_399_MOESM1_ESM.doc
The characterization data of Gd1, Gd2, Lu1, Lu2, Yb1 and Yb2 in this work. In addition, the CCDC numbers for Gd1, Gd2, Lu1, Lu2, Yb1 and Yb2 were 1968346, 1968347, 1968352, 1968353, 1968349 and 1968350. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html, or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk. (DOC 837 kb)
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Wang, R., Zou, BQ., Qin, QP. et al. Synthesis, characterization and the anticancer activity of six lanthanides(III) complexes with 5,7-dihalogenated-8-quinolinol and 2,2’-bipyridine derivatives. Transit Met Chem 45, 477–483 (2020). https://doi.org/10.1007/s11243-020-00399-4
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DOI: https://doi.org/10.1007/s11243-020-00399-4