Một chất chống phát triển tế bào mới dựa trên palladium: tổng hợp, đặc trưng, tính toán, độc tính tế bào và tính chất gắn kết DNA

Adamo C, Barone V (1998) Exchange functionals with improved long-range behavior and adiabatic connection methods without adjustable parameters: The m PW and m PW1PW models. J Chem Phys 108:664–675 Adrian RA, Broker GA, Tiekink ERT, Walmsley JA (2008) Palladium (II) complexes of 1, 10-phenanthroline: Synthesis and X-ray crystal structure determination. Inorg Chim Acta 361:1261–1266 Aminzadeh M, Eslami A, Kia R, Aleeshah R (2017a) Synthesis, crystal structure, DFT calculation and DNA binding studies of new water-soluble derivatives of dppz. J Mol Struct 1145:141–151 Aminzadeh M, Mansouri-Torshizi H, Modarresi-Alam AR (2017b) 2, 2′-bipyridine coplanar with coordination square of Pd (II) nonyldithiocarbamato antitumor complex interacting with DNA in two distinct steps. J Biomol Struct Dyn 35:2301–2313 Aminzadeh M, Eslami A, Kia R, Aleeshah R (2018) Synthesis, crystal structure and DNA interaction of a new water-soluble derivative of pyrazino [2, 3-f][1, 10] phenanthroline; theoretical calculations, experimental and molecular docking studies. J Mol Struct 1165:267–275 Aminzadeh M, Saeidifar M, Mansouri-Torshizi H (2020), Synthesis, characterization, DNA binding, cytotoxicity, and molecular docking approaches of Pd (II) complex with N, O-donor ligands as a novel potent anticancer agent. J Mol Str 128212. Angeles-Boza AM, Bradley PM, Fu PK-L, Wicke SE, Bacsa J, Dunbar KR, Turro C (2004) DNA binding and photocleavage in vitro by new dirhodium (II) dppz complexes: correlation to cytotoxicity and photocytotoxicity. Inorg Chem 43:8510–8519 Atasever B, Ülküseven B, Bal-Demirci T, Erdem-Kuruca S, Solakoǧlu Z (2010) Cytotoxic activities of new iron(III) and nickel(II) chelates of some S-methyl-thiosemicarbazones on K562 and ECV304 cells. Invest New Drugs 28:421–432 Barbee J, Kuznetsov AE (2012) Revealing substituent effects on the electronic structure and planarity of Ni-porphyrins. Comput Theor Chem 981:73–85 Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652 Bolognesi P, Mattioli G, O’Keeffe P, Feyer V, Plekan O, Ovcharenko Y, Prince K, Coreno M, Amore Bonapasta A, Avaldi L (2009) Investigation of halogenated pyrimidines by X-ray photoemission spectroscopy and theoretical DFT methods. J Phys Chem A 113:13593–13600 Bushnell EAC, Boyd RJ (2015) Assessment of several DFT functionals in calculation of the reduction potentials for Ni–, Pd–, and Pt–Bis-ethylene-1, 2-dithiolene and-diselenolene complexes. J Phys ChemA 119:911–918 Calligaris M, Zangrando E, Milani B, Marson A (2005) Stereochemical investigation of palladium (II) complexes with phenanthroline ligands: a molecular mechanics approach. Eur J Inorg Chem 2005:704–712 Cances E, Mennucci B, Tomasi J (1997) A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics. J Chem Phys 107:3032–3041 Carbonell E, Martinez-Camarena A, Galiana-Rosello C, Inclan M, Tejero R, Yunta M, Navarro P, Gomez-Contreras F, Sanz A, Campayo L (2019) Acid–base behaviour and binding to double stranded DNA/RNA of benzo [g] phthalazine-based ligands. New J Chem 43:700–708 Check CE, Faust TO, Bailey JM, Wright BJ, Gilbert TM, Sunderlin LS (2001) Addition of polarization and diffuse functions to the LANL2DZ basis set for p-block elements. J Phys Chem A 105(34):8111–8116 Deegan C, Coyle B, McCann M, Devereux M, Egan DA (2006) In vitro anti-tumour effect of 1, 10-phenanthroline-5, 6-dione (phendione),[Cu (phendione) 3](ClO 4) 2· 4H 2 O and [Ag (phendione) 2] ClO 4 using human epithelial cell lines. Chem Biol Interact 164:115–125 Dennington R, Keith T, Millam J (2009) GaussView, version 5. Semichem Inc., Shawnee Mission, KS Dikmen G, Ünver H (2021) A new Pd (II)-Hydrazide-Triphenylphosphine complex: Synthesis, crystal structure, spectroscopic characterization and theoretical calculations. J Mol Str 1225:129139 Divsalar A, Saboury AA, Mansoori-Torshizi H, Ahmad F (2010) Design, synthesis, and biological evaluation of a new palladium (II) complex: β-lactoglobulin and K562 as targets. J Phys Chem B 114:3639–3647 Dreuw A, Dunietz BD, Head-Gordon M (2002) Characterization of the relevant excited states in the photodissociation of CO-ligated hemoglobin and myoglobin. J Am Chem Soc 124:12070–12071 Duan R-R, Ou Z-B, Wang W, Chen S, Zhou X-H (2015) Synthesis, crystal structures, photoluminescence properties and DNA binding of triazine–nickel (II) complexes for DNA detection. Spectrochim Acta Part A Mol Biomol Spectrosc 151:64–71 Eslami Moghadam M, Saidifar M, Divsalar A, Mansouri-Torshizi H, Saboury AA, Farhangian H, Ghadamgahi M (2016) Rich spectroscopic and molecular dynamic studies on the interaction of cytotoxic Pt (II) and Pd (II) complexes of glycine derivatives with calf thymus DNA. J Biomol Str Dynam 34:206–222 Fatahian-Nezhad M, Alizadeh R, Mohammadi SS, Tohidlou M, Naderi-Manesh H, Amani V (2021) Synthesis, characterization, structural studies, DNA interaction, and cytotoxic studies of palladium (II) mixed-ligand complexes containing 2, 2′-bipyridine, 5, 6-dimethyl-1, 10-phenanthroline and tetrazole-5-thiol ligands. Inorg Chim Acta 514:119953 Ferreira LG, dos Santos RN, Oliva G, Andricopulo AD (2015) Molecular docking and structure-based drug design strategies. Molecules 20:13384–13421 Frisch MJ, Pople JA, Stephen Binkley J (1984) Self-consistent molecular orbital methods 25 Supplementary functions for Gaussian basis sets. J Chem Phys 80(7):3265–3269 Fuentes L, Quiroga AG, Organero JA, Matesanz AI (2020) Exploring DNA binding ability of two novel α-N-heterocyclic thiosemicarbazone palladium (II) complexes. J Inorgan Biochem 203:110875 Gaussian RA, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA et al (2009) Gaussian, Inc., Wallingford CT Ghosh S, Barve AC, Kumbhar AA, Kumbhar AS, Puranik VG, Datar PA, Sonawane UB, Joshi RR (2006) Synthesis, characterization, X-ray structure and DNA photocleavage by cis-dichloro bis (diimine) Co (III) complexes. J Inorg Biochem 100:331–343 Gill MR, Thomas JA (2012) Ruthenium (II) polypyridyl complexes and DNA—from structural probes to cellular imaging and therapeutics. Chem Soc Rev 41:3179–3192 Hildebrandt J, Trautwein R, Kritsch D, Häfner N, Görls H, Dürst M, Runnebaum IB, Weigand W (2019) Synthesis, characterization and biological investigation of platinum (II) complexes with asparagusic acid derivatives as ligands. Dalton Trans 48:936–944 Howe-Grant M, Wu KC, Bauer WR, Lippard SJ (1976) Binding of platinum and palladium metallointercalation reagents and antitumor drugs to closed and open DNAs. Biochemistry 15:4339–4346 Islami-Moghaddam M, Mansouri-Torshizi H, Divsalar A, Saboury A (2009) Synthesis, characterization, cytotoxic and DNA binding studies of diimine platinum (II) and palladium (II) complexes of short hydrocarbon chain ethyldithiocarbamate ligand. J Iran Chem Soc 6:552–569 Jahanian-Najafabadi A, Mirian M, Rohani F, Karami K, Hosseini Kharat M, Sadeghi-Aliabadi H (2019) Novel palladium complex: cytotoxicity against cisplatin-resistant K562 cells. Iran J Pharmac Res 18(3):1323–1331 Kenny RG, Marmion CJ (2019) Toward multi-targeted platinum and ruthenium drugs—a new paradigm in cancer drug treatment regimens. Chem Rev 119:1058–1137 Klamt A, Moya C, Palomar J (2015) A comprehensive comparison of the IEFPCM and SS (V) PE continuum solvation methods with the COSMO approach. J Chem Theory Comput 11:4220–4225 Kljun J, León IE, Peršič Š, Cadavid-Vargas JF, Etcheverry SB, He W, Bai Y, Turel I (2018) Synthesis and biological characterization of organoruthenium complexes with 8-hydroxyquinolines. J Inorg Biochem 186:187–196 Komjáti B, Urai Á, Hosztafi S, Kökösi J, Kováts B, Nagy J, Horváth P (2016) Systematic study on the TD-DFT calculated electronic circular dichroism spectra of chiral aromatic nitro compounds: A comparison of B3LYP and CAM-B3LYP. Spectrochim Acta Part A Mol Biomol Spectrosc 155:95–102 Kondori T, Akbarzadeh-T N, Ghaznavi H, Karimi Z, Shahraki J, Sheervalilou RO, Shahraki O (2020) A binuclear iron(III) complex of 5,5′-dimethyl-2,2′-bipyridine as cytotoxic agent. Biometals 33:365–378 Lazou M, Tarushi A, Gritzapis P, Psomas G (2020) Transition metal complexes with a novel guanine-based (E)-2-(2-(pyridin-2-ylmethylene) hydrazinyl) quinazolin-4 (3H)-one: Synthesis, characterization, interaction with DNA and albumins and antioxidant activity. J Inorgan Biochem 206:111019 Lenaerts P et al (2005) Thin Films of highly luminescent lanthanide complexes covalently linked to an organic− inorganic hybrid material via 2-substituted imidazo [4, 5-f]-1, 10-phenanthroline groups. Chem Mater 20:5194–5201 Lenaerts P, Storms A, Mullens J, D’Haen J, Görller-Walrand C, Binnemans K, Driesen K (2005) Thin Films of highly luminescent lanthanide complexes covalently linked to an organic− inorganic hybrid material via 2-substituted imidazo [4, 5-f]-1, 10-phenanthroline groups. Chem Mater 17:5194–5201 Liu X, Yang D, Ju H, Teng F, Hou Y, Lou Z (2011) Experimental and PCM/TD-DFT investigation on the absorption and emission spectra of a light emitting material in various solvents. Chem Phys Lett 503(1–3):75–79 Ma L, Ge K, Zhang R, Fu W, Li S, Wang S, Zhou G, Qin X, Zhang J (2014) Synthesis, characterization, cytotoxicity of mixed ligand complexes of palladium (II) with dipyrido [3, 2-d: 2′, 3′-f] quinoxaline/dipyrido [3, 2-a: 2′, 3′-c](6, 7, 8, 9-tetrahydro) phenazine and 4-toluensulfonyl-L-amino acid dianion. Eur J Med Chem 87:624–630 Makedonas C, Mitsopoulou CA, Lahoz FJ, Balana AI (2003) Synthesis, characterization, and crystal structure of the Pd (phen)(bdt) complex. A DFT and TDDFT study of its ground electronic and excited states compared to those of analogous complexes. Inorgan Chem 42:8853–8865 Manojkumar Y, Ambika S, Senthilkumar R, Arunachalam S (2017) Biophysical and biological studies of some polymer grafted metallo-intercalators. Colloids Surf, B 156:320–329 Mansouri-Torshizi H, Mahboube I, Divsalar A, Saboury A-A (2008) 2, 2′-Bipyridinebutyldithiocarbamatoplatinum (II) and palladium (II) complexes: synthesis, characterization, cytotoxicity, and rich DNA-binding studies. Bioorg Med Chem 16:9616–9625 Mansouri-Torshizi H, Moghaddam M, Divsalar A, Saboury A (2009) Diimine platinum (II) and palladium (II) complexes of dithiocarbamate derivative as potential antitumor agents: synthesis, characterization, cytotoxicity, and detail DNA-binding studies. J Biomol Struct Dyn 26:575–586 Mansouri-Torshizi H, Saeidifar M, Divsalar A, Saboury AA (2010a) Interaction studies between a 1, 10-phenanthroline adduct of palladium (II) dithiocarbamate anti-tumor complex and calf thymus DNA. A synthesis spectral and in-vitro study. Spectrochim Acta Part A 77:312–318 Mansouri-Torshizi H, Saeidifar M, Rezaei-Behbehani G, Divsalar A, Saboury A (2010b) DNA binding studies and cytotoxicity of ethylenediamine 8-hydroxyquinolinato palladium (II) chloride. J Chin Chem Soc 57:1299–1308 Mansouri-Torshizi H, Saeidifar M, Divsalar A, Saboury AA (2010c) Interaction studies between a 1,10-phenanthroline adduct of palladium(II) dithiocarbamate anti-tumor complex and calf thymus DNA. A synthesis spectral and in-vitro study. Spectrochim Acta Part A 77:312–318 Matesanz AI, Jimenez-Faraco E, Ruiz MC, Balsa LM, Navarro-Ranninger C, León IE, Quiroga AG (2018) Mononuclear Pd (II) and Pt (II) complexes with an α-N-heterocyclic thiosemicarbazone: cytotoxicity, solution behaviour and interaction versus proven models from biological media. Inorganic Chemistry Frontiers 5:73–83 McNaught AD, Wilkinson A (1997) Compendium of chemical terminology, Blackwell Science Oxford Mohammadi F, Mansouri-Torshizi H (2020) Five novel palladium (II) complexes of 8-hydroxyquinoline and amino acids with hydrophobic side chains: synthesis, characterization, cytotoxicity DNA-and BSA-interaction studies. J Biomol Str Dynam 38:3059–3073 Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, Olson AJ (2009) AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem 30:2785–2791 Musthafa M, Konakanchi R, Ganguly R, Balachandran C, Aoki S, Sreekanth A (2020) Synthesis, characterization, theoretical, molecular docking and in vitro biological activity studies of Ru (II)(η6-p-cymene) complexes with novel aniline substituted aroyl selenoureas. J Biomol Str Dynam 1–16. Nakamoto K (2008) Infrared and raman spectra of inorganic and coordination compounds, theory and applications in inorganic chemistry, Wiley Noodeh MF, Divsalar A, Seyedarabi A, Saboury AA (2018) Antiproliferative and interaction studies of a synthesized palladium (II) complex with human hemoglobin. J Mol Liq 249:265–271 Nwokeoji AO, Kilby PM, Portwood DE, Dickman MJ (2017) Accurate quantification of nucleic acids using hypochromicity measurements in conjunction with UV spectrophotometry. Anal Chem 89:13567–13574 Özerkan D, Ertik O, Kaya B, Kuruca SE, Yanardag R, Ülküseven B (2019) Novel palladium (II) complexes with tetradentate thiosemicarbazones synthesis, characterization, in vitro cytotoxicity and xanthine oxidase inhibition. Invest New Drugs 37:1187–1197 Peng X-H, Wang Y, Huang D, Wang Y, Shin HJ, Chen Z, Spewak MB, Mao H, Wang X, Wang Y (2011) Targeted delivery of cisplatin to lung cancer using ScFvEGFR-heparin-cisplatin nanoparticles. ACS Nano 5:9480–9493 Perdew JP, Burke K, Wang Y (1996) Generalized gradient approximation for the exchange-correlation hole of a many-electron system. Phys Rev B 54:16533–16539 Ramachandran E, Senthil Raja D, Rath NP, Natarajan K (2013) Role of substitution at terminal nitrogen of 2-oxo-1, 2-dihydroquinoline-3-carbaldehyde thiosemicarbazones on the coordination behavior and structure and biological properties of their palladium (II) complexes. Inorgan Chem 52:1504–1514 Saeidifar M, Mansouri-Torshizi H, Palizdar Y, Eslami-Moghaddam M, Divsalar A, Saboury AA (2014) Synthesis, characterization, cytotoxicity and DNA binding studies of a novel anionic organopalladium (II) complex. Acta Chim Slov 61:126–136 Saeidifar M, Mansouri-Torshizi H, Saboury AA (2015) Biophysical study on the interaction between two palladium (II) complexes and human serum albumin by Multispectroscopic methods. J Lumin 167:391–398 Sathyaraj G, Weyhermüller T, Nair BU (2010) Synthesis, characterization and DNA binding studies of new ruthenium (II) bisterpyridine complexes. Eur J Med Chem 45:284–291 Savić A, Marzo T, Scaletti F, Massai L, Bartoli G, Hoogenboom R, Messori L, Deun RV, Hecke KV (2019) New platinum(II) and palladium(II) complexes with substituted terpyridine ligands: synthesis and characterization, cytotoxicity and reactivity towards biomolecules. Biometals 32:33–47 Scarpantonio L, Cotton S, Del Giorgio E, McCallum M, Hannon M, Pikramenou Z (2020) A luminescent europium hairpin for DNA photosensing in the visible, based on trimetallic bis-intercalators. J Inorgan Biochem 111119. Scatchard G (1949) The attractions of proteins for small molecules and ions. Ann N Y Acad Sci 51:660–672 Singh SB, Kumbhar AS, Khan A (2016) Honeycomb-like ordered assembly of dna induced by flexible binuclear ruthenium (II)–polypyridyl complexes. Chemistry-A Eur J 22:15760–15771 Sorinezami Z, Mansouri-Torshizi H (2016) Photo-catalytic degradation of organic dyes: ultrasonic-assisted synthesis of PdO nanoparticles. J Mater Sci: Mater Electron 27:1558–1565 Sorinezami Z, Mansouri-Torshizi H, Aminzadeh M, Ghahghaei A, Jamgohari N, Heidari Majd M (2019) Synthesis of new ultrasonic-assisted palladium oxide nanoparticles: an in vitro evaluation on cytotoxicity and DNA/BSA binding properties. J Biomol Str Dynam 37:4238–4250 Stratmann RE, Scuseria GE, Frisch MJ (1998) An efficient implementation of time-dependent density-functional theory for the calculation of excitation energies of large molecules. J Chem Phys 109:8218–8224 Talarico T, Phillips DR, Deacon GB, Rainone S, Webster LK (1999) Activity and DNA binding of new organoamidoplatinum (II) complexe. Invest New Drugs 17:1–15 Terenzi A, Ducani C, Blanco V, Zerzankova L, Westendorf AF, Peinador C, Quintela JM, Bednarski PJ, Barone G, Hannon MJ (2012) DNA binding studies and cytotoxicity of a dinuclear PtII diazapyrenium-based metallo-supramolecular rectangular box. Chem-A Eur J 18:10983–10990 Wang Y, Okabe N (2005) X-ray structure characterization of palladium (II) ternary complexes of pyridinedicarboxylic and phthalic acid with phenanthroline and bipyridine. Chem Pharm Bull 53:366–373 Wei X, Yang Y, Ge J, Lin X, Liu D, Wang S, Zhang J, Zhou G, Li S (2020) Synthesis, characterization, DNA/BSA interactions and in vitro cytotoxicity study of palladium (II) complexes of hispolon derivatives. J Inorgan Biochem 202:110857 Xu H, Zheng K-C, Chen Y, Li Y-Z, Lin L-J, Li H, Zhang P-X, Ji L-N (2003) Effects of ligand planarity on the interaction of polypyridyl Ru (II) complexes with DNA. Dalton Trans. https://doi.org/10.1039/B300353A Yadav S, Yousuf I, Usman M, Ahmad M, Arjmand F, Tabassum S (2015) Synthesis and spectroscopic characterization of diorganotin (IV) complexes of N′-(4-hydroxypent-3-en-2-ylidene) isonicotinohydrazide: chemotherapeutic potential validation by in vitro interaction studies with DNA/HSA DFT, molecular docking and cytotoxic activity. RSC Adv 5:50673–50690 Yanai T, Tew DP, Handy NC (2004) A new hybrid exchange–correlation functional using the Coulomb-attenuating method (CAM-B3LYP). Chem Phys Lett 393:51–57 Zhu M-C, Cui X-T, Zhao F-C, Ma X-Y, Han Z-B, Gao E-J (2015) Synthesis, characterization, and DNA interaction of novel Pt (ii) complexes and their cytotoxicity, apoptosis and molecular docking. RSC Adv 5:47798–47808 Zhu X, Peng Y, Qiu L (2017) Amino-functionalized nano-vesicles for enhanced anticancer efficacy and reduced myelotoxicity of carboplatin. Colloids Surf, B 157:56–64 Zianna A, Ristović MŠ, Psomas G, Hatzidimitriou A, Coutouli-Argyropoulou E, Lalia-Kantouri M (2016) Cadmium (II) complexes of 5-bromo-salicylaldehyde and α-diimines: synthesis, structure and interaction with calf-thymus DNA and albumins. Polyhedron 107:136–147 Živković M, Kljun J, Ilic-Tomic T, Pavic A, Veselinović A, Manojlović D, Nikodinovic-Runic J, Turel I (2018) A new class of platinum (II) complexes with the phosphine ligand pta which show potent anticancer activity. Inorgan Chem Front 5:39–53