Iron Corrole Complexes: DNA-Binding and Anti-tumor Activity

doi:10.11944/j.issn.1000-0518.2019.12.190066

Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (12): 1376-1386.DOI: 10.11944/j.issn.1000-0518.2019.12.190066

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Iron Corrole Complexes: DNA-Binding and Anti-tumor Activity

SHI Lei^a^*(),YANG Wencong^a,SHEN Qi^a,YIN Wei^a,HUO Zhaohui^a,SI Liping^b,LIU Haiyang^c

^aDepartment of Chemistry,Guangdong University of Education,Guangzhou 510303,China
^bSchool of Materials Science and Energy Engineering,Foshan University,Guangdong Foshan 528000,China
^cKey Laboratory of Functional Molecular Engineering of Guangdong Province,South China University of Technology,Guangzhou 510640,China

Received:2019-03-14 Accepted:2019-06-25 Published:2019-12-01 Online:2019-12-10
Contact: SHI Lei
Supported by:
Supported by the Higher Education Teaching Reform Project in Guangdong Province(2018), the Open Fund Project of Foshan University(2018), the Special Funds for Guangdong University Students' Climbing Plan, College Students Innovation and Entrepreneurship Training Program, the Teaching Quality and Teaching Reform in Guangdong Second Normal University(2018), and the Innovation and Strong School Funding from Guangdong University of Education-Foundation for Distinguished Young Talents in Higher Education of Guangdong(No.2016KQNCX112)

Abstract

Abstract:

10-(4-Phenothiazine)-5,15-bis(pentafluorophenyl)corrolatoiron (2-Fe) was synthesized. Complex 2-Fe displays high cytotoxic activity against human lung adenocarcinoma (A549) cell lines. Flow cytometry detected 2-Fe arrested the cell cycle in the S and G2 phase in the presence of H₂O₂ and apoptotic rate was 63.76%. Hoechst-33342 staining showed considerable morphological changes in nuclear chromatin and mitochondrial transmembrane potential dropped respectively. Complex 2-Fe could interact with DNA via an outside binding mode and trigger ¹O₂ generation.

Key words: corrole, phenothiazine, DNA, cytotoxicity, iron, apoptosis

SHI Lei, YANG Wencong, SHEN Qi, YIN Wei, HUO Zhaohui, SI Liping, LIU Haiyang. Iron Corrole Complexes: DNA-Binding and Anti-tumor Activity[J]. Chinese Journal of Applied Chemistry, 2019, 36(12): 1376-1386.

References

[1]	Liu H Y,Mahmood M H R,Qiu S X,et al. Recent Developments in Manganese Corrole Chemistry[J]. Coord Chem Rev,2013,267:1306-1333.
[2]	Aviv-Harel I,Gross Z.Coordination Chemistry of Corroles with Focus on Main Group Elements[J]. Coord Chem Rev,2011,255:717-736.
[3]	Aviv I,Gross Z.Corrole-based Applications[J]. Chem Commun,2007:1987-1999.
[4]	Aviezer D,Cotton S,David M,et al. Porphyrin Analogues as Novel Antagonists of Fibroblast Growth Factor and Vascular Endothelial Growth Factor Receptor Binding that Inhibit Endothelial Cell Proliferation, Tumor Progression, and Metastasis[J]. Cancer Res,2000,60:2973-2980.
[5]	Chang C K,Kong P W,Liu H Y,et al. Synthesis and Photodynamic Activities of Modified Corrole Derivatives on Nasopharyngeal Carcinoma Cells[J]. Proc SPIE,2006,6139:613915-1.
[6]	Agadjanian H,Ma J,Rentsendorj A,et al. Tumor Detection and Elimination by a Targeted Gallium Corrole[J]. Proc Natl Acad Sci,2009,106:6105-6110.
[7]	Fu B Q,Huang J,Ren L,et al. Cationic Corrole Derivatives:A New Family of G-Quadruplex Inducing and Stabilizing Ligands[J]. Chem Commun,2007:3624-3266.
[8]	Fu B Q,Zhang D,Weng X C,et al. Cationic Metal-Corrole Complexes:Design, Synthesis, and Properties of Guanine-Quadruplex Stabilizers[J]. Chem Eur J,2008,14:9431-9441.
[9]	Ma H,Zhang M,Zhang D,et al. Pyridyl-Substituted Corrole Isomers:Synthesis and Their Regulation to G-Quadruplex Structures[J]. Chem Asian J,2010,5:114-122.
[10]	Qi L,Ding Y Q.Potential Antitumor Mechanisms of Phenothiazine Drugs[J]. Sci China Life Sci,2013,56:1020-1027.
[11]	Molnar J,Sakaqami H,Motohashi N.Diverse Biological Activities Displayed by Phenothiazines, Benzo[A]phenothiazines and Benz[C]acridins(Review)[J]. Anticancer Res,1993,13:1019-1025.
[12]	Shi L,Liu H Y,Peng K M,et al. Synthesis of Phenothiazine-corrole Dyads:The Enhanced DNA Photocleavage Properties[J]. Tetrahedron Lett,2010,51:3439-3442.
[13]	SHI Lei,JIANG Huanfeng,YIN Wei,et al. Synthesis, Fluorescence and DNA Photocleavage Activity of Phenothiazine-Corrole Gallium(Ⅲ) Complexes[J]. Acta Phys Chim,2012,28(2):465-469(in Chinese). 史蕾,江焕峰,尹伟,等. 吩噻嗪-Corrole镓(Ⅲ)配合物的合成、荧光及其光断裂DNA性质[J]. 物理化学学报,2012,28(2):465-469.
[14]	SHI Lei,YANG Wencong,ZENG Shuying,et al. DNA-Binding and Anti-tumor Activities of Cobalt Corrole Complexes[J]. Chem J Chinese Univ,2016,37:1059-1068(in Chinese). 史蕾,杨文聪,曾淑莹,等. 咔咯钴(Ⅲ)配合物与DNA 的相互作用及抗肿瘤活性[J]. 高等学校化学学报,2016,37:1059-1068.
[15]	Zhang Y,Wen J Y,Mahmood M H R,et al. DNA/HSA Interaction and Nuclease Activity of an Iron(Ⅲ) Amphiphilic Sulfonated Corrole[J]. Luminescence,2015,30:1045-1054.
[16]	Mahammed A,Gross Z.Iron and Manganese Corroles are Potent Catalysts for the Decomposition of Peroxynitrite[J]. Angew Chem Int Ed,2006,45:6544-6547.
[17]	Haber A,Mahammed A,Fuhrman B,et al. Amphiphilic/Bipolar Metallocorroles that Catalyze the Decomposition of Reactive Oxygen and Nitrogen Species, Rescue Lipoproteins from Oxidative Damage, and Attenuate Atherosclerosis in Mice[J]. Angew Chem Int Ed,2008,47:7896-7900.
[18]	Zhong Y Q,Md.Hossain S,Chen Y,et al. A Comparative Study of Electrocatalytic Hydrogen Evolution by Iron Complexes of Corrole and Porphyrin from Acetic Acid and Water[J]. Transition Met Chem,2019,44:399-406.
[19]	Zou H B,Yang H,Liu Z Y,et al. Iron(Ⅳ)-Corrole Catalyzed Stereoselective Olefination of Aldehydes with Ethyl Diazoacetate[J]. Organometallics,2015,34:2791-2795.
[20]	Nakano K,Kobayashi K,Ohkawara T,et al. Copolymerization of Epoxides with Carbon Dioxide Catalyzed by Iron-Corrole Complexes:Synthesis of a Crystalline Copolymer[J]. J Am Chem Soc,2013,135:8456-8459.
[21]	Lepecq J B,Paoletti C.A Fluorescent Complex Between Ethidium Bromide and Nucleic Acids. Physical-Chemical Characterization[J]. J Mol Biol,1967,27:87-106.
[22]	Sun Y,Hou Y J,Zhou Q X,et al. Dinuclear Cu(Ⅱ) Hypocrellin B Complexes with Enhanced Photonuclease Activity[J]. Inorg Chem,2010,49:10108-10116.
[23]	Satyanarayana S,Dabrowiak J C,Chaires J B,et al. Tris(phenanthroline)ruthenium(Ⅱ) Enantiomer Interactions with DNA:Mode and Specificity of Binding[J]. Biochemistry,1993,32:2573-2584.
[24]	Banmeyer I,Marchand C,Verhaeghe C,et al. Overexpression of Human Peroxiredoxin 5 in Subcellular Compartments of Chinese Hamster Ovary Cells:Effects on Cytotoxicity and DNA Damage Caused by Peroxides[J]. Free Radical Biol Med,2004,36:65-77.
[25]	Ghosh A.Electronic Structure of Corrole Derivatives:Insights from Molecular Structures, Spectroscopy, Electrochemistry, and Quantum Chemical Calculations[J]. Chem Rev,2017,117:3798-3881.
[26]	Xiang J Y,Xia X S,Jiang Y,et al. Apoptosis of Ovarian Cancer Cells Induced by Methylene Blue-Mediated Sonodynamic Action[J]. Ultrasonics,2011,51:390-395.
[27]	Domingo-Gil E,Esteban M.Role of Mitochondria in Apoptosis Induced by the 2-5A System and Mechanisms Involved[J]. Apoptosis,2006,11:725-738.
[28]	Zhao C Q,Zhang Y H,Jiang S D,et al. Both Endoplasmic Reticulum and Mitochondria are Involved in Disc Cell Apoptosis and Intervertebral Disc Degeneration in Rats[J]. AGE,2010,32:161-177.
[29]	Green D R,Reed J C.Mitochondria and Apoptosis[J]. Science,1998,28:1309-1312.
[30]	Yun-Kai L V,Li P,Jiao M L,et al. Fluorescence Quenching Study of Moxifloxacin Interaction with Calf Thymus DNA[J]. Turk J Chem,2014,38:202-209.
[31]	Lakowicz J R,Webber G.Quenching of Fluorescence by Oxygen. A Probe for Structural Fluctuations in Macromoleculest[J]. Biochemisry,1973,12:4161-4170.
[32]	Sun Y T,Peng T T,Zhao L,et al. Studies of Interaction Between Two Alkaloids and Double Helix DNA[J]. J Lumin,2014,156:108-115.
[33]	Pasternack R F,Gibbs E J,Villafranca J J.Interactions of Porphyrins with Nucleic Acids[J]. Biochemistry,1983,22:2406-2414.
[34]	Wolfe A,Shimer G H,Meehan T.Polycyclic Aromatic Hydrocarbons Physically Intercalate into Duplex Regions of Denatured DNA[J]. Biochemistry,1987,26:6392-6396.
[35]	Ivanov V I,Minchenkova L E,Schyolkina A K,et al. Different Conformations of Double-stranded Nucleic Acid in Solution as Revealed by Circular Dichroism[J]. Biopolymers,1973,12:89-110.
[36]	Nordén B, Tjerneld F.Structure of Methylene Blue-DNA Complexes Studied by Linear and Circular Dichroism Spectroscopy[J]. Biopolymers,1982,21:1713-1734.
[37]	Satyanarayana S,Dabrowiak J C,Chaires J B.Neither Δ- nor Λ-Tris(phenanthroline)ruthenium(Ⅱ) Binds to DNA by Classical Intercalation[J]. Biochemistry,1992,31:9319-9324.
[38]	Ji L N,Zhou X H,Liu J G.Shape and Enantioselective Interaction of Ru(Ⅱ)/Co(Ⅲ) Polypyridyl Complexes with DNA[J]. Coord Chem Rev,2001,216:513-536.
[39]	Inclán M,Albelda M T,Frías J C,et al. Modulation of DNA Binding by Reversible Metal-Controlled Molecular Reorganizations of Scorpiand-Like Ligands[J]. J Am Chem Soc,2012,134:9644-9656.
[40]	Enko B,Borisov S M,Regensburger J,et al. Singlet Oxygen-Induced Photodegradation of the Polymers and Dyes in Optical Sensing Materials and the Effect of Stabilizers on These Processes[J]. J Phys Chem A,2013,117:8873-8882.
[41]	Bancirova M.Sodium Azide as a Specific Quencher of Singlet Oxygen During Chemiluminescent Detection by Luminol and Cypridina Luciferin Analogues[J]. Luminescence,2011,26:685-688.
[42]	Lee J W,Miyawaki H,Bobst E V.Improved Functional Recovery of Ischemic Rat Hearts Due to Singlet Oxygen Scavengers Histidine and Carnosine[J]. J Mol Cell Cardiol,1999,31:113-121.
[43]	Stoyanovsky D A,Melnikov Z,Cederbaum A I.ESR and HPLC-EC Analysis of the Interaction of Hydroxyl Radical with DMSO:Rapid Reduction and Quantification of POBN and PBN Nitroxides[J]. Anal Chem,1999,71:715-721.
[44]	Staehelln J,Hoign J.Decomposition of Ozone in Water in the Presence of Organic Solutes Acting as Promoters and Inhibitors of Radical Chain Reactionst[J]. Environ Sci Technol,1985,19:1206-1213.

Iron Corrole Complexes: DNA-Binding and Anti-tumor Activity

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