DNA and BSA-Binding Studies of Dinuclear Palladium(II) Complexes with 1,5-Naphtiridine Bridging Ligands

Rajkovic, Snezana; Franich, Andjela A.; Cupurdija, Vojislav; Zivkovic, Marija D.

doi:10.2478/sjecr-2021-0030

Abstract

The interactions of metal complexes with important biomolecules such as deoxyribonucleic acid (DNA) or bovine serum albumin (BSA) are responsible for their antitumor activity due to different modes of interaction with DNA and their transport through the blood system to cells and tissues via serum albumin. Therefore, the dinuclear palladium(II) complexes, [{Pd(en)Cl}₂(μ-1,5-nphe)](NO₃)₂ (Pd1) and [{Pd(1,3-pd)Cl}₂(μ-1,5-nphe)](NO₃)₂ (Pd2) (en is ethylenediamine, 1,3-pd is 1,3-propylenediamine and 1,5-nphe is the bridging 1,5-naphthyridine ligand) were synthesized and characterized by different spectroscopic methods. The UV-Vis and fluorescence emission spectroscopy were applied for evaluation of binding modes of Pd1 and Pd2 complexes to DNA as well as their interaction with BSA. The emission spectra indicate that the investigated Pd1 and Pd2 complexes can displace the ethidium bromide intercalator from DNA/EtBr molecules and act as intercalators showing strong interactions with DNA. The fluorescence intensity showes that Pd1 and Pd2 complexes can bind to BSA and then be transported to the cell.

References

Cotton FA, Wilkinson G. Advanced inorganic chemistry, John Wiley & Sons Inc., New York, (1972).
Search in Google Scholar Back to article
Janković V. Hemijski elementi, Zavod za udžbenike i nastavna sredstva, Beograd, 2002.
Search in Google Scholar Back to article
Matwiyoff A, Asprey LB, Wageman WE, Reisfeld MJ, Fukushima E. Fluorine-19 nuclear magnetic resonance studies of diamagnetic fluoride complexes of nickel(IV), palladium(IV), and platinum(IV) in anhydrous hydrogen fluoride solutions. Inorg. Chem., 1969;8(4):750–753.
Search in Google Scholar Back to article
Butour JL, Wimmer S, Wimmer F, Castan P. Palladium(II) compounds with potential antitumour properties and their platinum analogues: a comparative study of the reaction of some orotic acid derivatives with DNA in vitro. Chem. Biol. Inter., 1997;104:165–178.
Search in Google Scholar Back to article
Navarro-Ranninger C, Pérez JM, Zamora F, González VM, Masaguer JR, Alonso C. Palladium(II) compounds of putrescine and spermine. Synthesis, characterization, and DNA-binding and antitumor properties. J. Inorg. Biochem. 1993;52:37–49.
Search in Google Scholar Back to article
Ray S, Mohan R, Singh JK, Samantaray MK, Shaikh MM, Panda D, Ghosh P. Anticancer and Antimicrobial Metallopharmaceutical Agents Based on Palladium, Gold, and Silver N-Heterocyclic Carbene Complexes. J.Am. Chem. Soc. 2007;129:15042–15053.
Search in Google Scholar Back to article
Storr T, Thompson KH, Orvig C. Design of targeting ligands in medicinal inorganic chemistry. Chem. Soc. Rev. 2006;35:534–544.
Search in Google Scholar Back to article
Zhao G, Sun H, Lin H, Zhu S, Su X, Chen Y. Palladium(II) complexes with N,N′-dialkyl-1,10-phenanthroline-2,9-dimathanamine: synthesis, characterization and cytotoxic activity. J. Inorg. Biochem. 1998;72:173–177.
Search in Google Scholar Back to article
Potters L, Cao Y, Calugaru E, Torre T, Fearn P, Wang XH. A comprehensive review of CT-based dosimetry parameters and biochemical control in patients treated with permanent prostate brachytherapy. Int. J. Radiat. Oncol. Biol. Phys. 2001;50:605–614.
Search in Google Scholar Back to article
Stone NN, Stock PG. Complications following permanent prostate brachytherapy. Eur. Urol. 2002;41:427–433.
Search in Google Scholar Back to article
Vujić JM, Cvijović M, Kaluderović GN, Milovanović M, Zmejkovski BB, Volarević V, Arsenijević N, Sabo TJ, Trifunović SR. Palladium(II) complexes with R2edda derived ligands. Part IV. O,O′-dialkyl esters of (S,S)-ethylenediamine-N,N′-di-2-(4-methyl)-pentanoic acid dihydrochloride and their palladium(II) complexes: Synthesis, characterization and in vitro antitumoral activity against chronic lymphocytic leukemia (CLL) cells. Eur. J. Med. Chem. 2010;45:3601–3606.
Search in Google Scholar Back to article
Ilić DR, Jevtić VV, Radić GP, Arsikin K, Ristić B, Harhaji-Trajković L, Vuković N, Sukdolak S, Klisurić O, Trajković V, Trifunović SR. Synthesis, characterization and cytotoxicity of a new palladium(II) complex with a coumarine-derived ligand. Eur. J. Med. Chem. 2014;74:502–508.
Search in Google Scholar Back to article
Zhao G, Lin H, Yu P, Sun H, Zhu S, Su X, Chen Y. Ethylenediamine-palladium(II) complexes with pyridine and its derivatives: synthesis, molecular structure and initial antitumor studies. J. Inorg. Biochem. 1999;73:145–149.
Search in Google Scholar Back to article
Gao E, Lin L, Liu L, Zhu M, Wang B, Gao X. Two new palladium(II) complexes: Synthesis, characterization and their interaction with HeLa cells. Dalton Trans. 2012;41:11187–11194.
Search in Google Scholar Back to article
Kapdi AR, Fairlamb IJS. Anti-cancer palladium complexes: a focus on PdX₂L₂, palladacycles and related complexes. Chem. Soc. Rev. 2014;43:4751–4777.
Search in Google Scholar Back to article
Cohen GL, Ledner JA, Bauer WR, Ushay HM, Caravana C, Lippard SJ. Sequence dependent binding of cisdichlorodiammineplatinum(II) to DNA. J. Am. Chem. Soc. 1980;102:2487–2488.
Search in Google Scholar Back to article
Takahara PM, Frederick CA, Lippard SJ. Crystal Structure of the Anticancer Drug Cisplatin Bound to Duplex DNA. J. Am. Chem. Soc. 1996;118:12309–12321.
Search in Google Scholar Back to article
Gately DP, Howell SB. Cellular accumulation of the anticancer agent cisplatin: a review. Br. J. Cancer 1993;67:1171–1176.
Search in Google Scholar Back to article
Komeda S, Kalayada GV, Lutz M, Spek AL, Yamanaka Y, Sato T, Chikuma M, Reedijk J. New Isomeric Azine-Bridged Dinuclear Platinum(II) Complexes Circumvent Cross-Resistance to Cisplatin. J. Med. Chem. 2003;46:1210–1219.
Search in Google Scholar Back to article
Ašanin DP, Živković MD, Rajković S, Warżajtis B, Rychlewska U, Djuran MI. Crystallographic evidence of anion⋯π interactions in the pyrazine bridged {[Pt(en)Cl]2(μ-pz)}Cl2 complex and a comparative study of the catalytic ability of mononuclear and binuclear platinum(II) complexes in the hydrolysis of N-acetylated l-methionylglycine. Polyhedron 2013;51:255–262.
Search in Google Scholar Back to article
Chen H, Parkinson JA, Parsons S, Coxall RA, Gould RO, Sadler PJ. Organometallic Ruthenium(II) Diamine Anticancer Complexes: Arene-Nucleobase Stacking and Stereospecific Hydrogen-Bonding in Guanine Adducts. J. Am. Chem. Soc. 2002;124:3064–3082.
Search in Google Scholar Back to article
Chen H, Parkinson JA, Nováková O, Bella J, Wang F, Dawson A, Gould R, Parsons S, Brabec V, Sadler PJ. Induced-fit recognition of DNA by organometallic complexes with dynamic stereogenic centers. Proc. Natl. Acad. Sci. U. S. A. 2003;100:14623–1428.
Search in Google Scholar Back to article
Carter D, Ho JX. Structure of Serum Albumin. Advances in Protein Chemistry 1994;45:153–203.
Search in Google Scholar Back to article
Curry S, Mandelkow H, Brick P, Franks N. Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites. Nat. Struct. Biol. 1998;5:827–835.
Search in Google Scholar Back to article
Brown JR, Shockley P. Lipid and Protein Interactions, Wiley, New York, 1 (1982).
Search in Google Scholar Back to article
Peters T. Serum albumin. Advances in Protein Chemistry 1985;37:161–245.
Search in Google Scholar Back to article
Reynolds JA, Herbert S, Polet H, Steinhardt J. The binding of divers detergent anions to bovine serum albumin. Biochemistry 1967;6:937–947.
Search in Google Scholar Back to article
Sklar LA, Hudson BS, Simoni RD. Conjugated polyene fatty acids as fluorescent probes: binding to bovine serum albumin. Biochemistry 1977;16:5100–5108.
Search in Google Scholar Back to article
Milinković SU, Parac TN, Djuran MI, Kostić NM. Dependence of hydrolytic cleavage of histidine-containing peptides by palladium(II) aqua complexes on the co-ordination modes of the peptides. J. Chem. Soc., Dalton Trans. (1997) 2771–2776.
Search in Google Scholar Back to article
Hohmann H, Eldik R. van. Rate and equilibrium data for substitution reactions of diaqua(ethylenediamine) palladium(II) with chloride in aqueous solution. Inorg. Chim.Acta 1990;174:87–92.
Search in Google Scholar Back to article
Živković MD, Ašanin DP, Rajković S, Djuran MI. Hydrolysis of the amide bond in N-acetylated l-methionylglycine catalyzed by various platinum(II) complexes under physiologically relevant conditions. Polyhedron 2011;30:947–952.
Search in Google Scholar Back to article
Franich AA, Živković MD, Ćoćić D, Petrović B, Milovanović M, Arsenijević A, Milovanović J, Arsenijević D, Stojanović B, Djuran MI, Rajković S. New dinuclear palladium(II) complexes with benzodiazines as bridging ligands: interactions with CT-DNA and BSA, and cytotoxic activity. J. Biol. Inorg. Chem. 2019;24:1009–1022.
Search in Google Scholar Back to article
Zhao G, Lin H, Zhu S, Sun H, Chen Y. Dinuclear palladium(II) complexes containing two monofunctional [Pd(en)(pyridine)Cl]+ units bridged by Se or S. Synthesis, characterization, cytotoxicity and kinetic studies of DNA-binding. J. Inorg. Biochem. 1998;70:219–226.
Search in Google Scholar Back to article
Komeda S, Kalayda GV, Lutz M, Spek AL, Yamanaka Y, Sato T, Chikuma M. J. Reedijk, New Isomeric Azine-Bridged Dinuclear Platinum(II) Complexes Circumvent Cross-Resistance to Cisplatin. J. Med. Chem. 2003;46:1210–1219.
Search in Google Scholar Back to article
Dimiza F, Fountoulaki S, Papadopoulos AN, Kontogiorgis CA, Tangoulis V, Raptopoulou CP, Psycharis V, Terzis A, Kessissoglou DP, Psomas G. Non-steroidal antiinflammatory drug–copper(ii) complexes: Structure and biological perspectives. Dalton Trans. 2011;40:8555–8568.
Search in Google Scholar Back to article
Dimiza F, Perdih F, Tangoulis V, Turel I, Kessissoglou DP, Psomas G. Interaction of copper(II) with the nonsteroidal anti-inflammatory drugs naproxen and diclofenac: Synthesis, structure, DNA- and albumin-binding. J. Inorg. Biochem. 2011;105:476–489.
Search in Google Scholar Back to article
Wolf A, Shimer GH, Meehan T. Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry 1987;26:6392–6396.
Search in Google Scholar Back to article
Liu M. Yuan W, Zhang Q, Yan L, Yang R. Synthesis, characterization and DNA interaction studies of complexes of lanthanide nitrates with tris{2-[(3,4-dihydroxybenzylidene) imino]ethyl}amine. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 2008;70:1114–1119.
Search in Google Scholar Back to article
Shahabadi N, Maghsudi MM, Ahmadipour Z. Study on the interaction of silver(I) complex with bovine serum albumin by spectroscopic techniques. Spectrochim. Acta, Part A 2012;92:184–188.
Search in Google Scholar Back to article
Li L, Qiong GQ, Dong J, Xu T, Li J. DNA binding, DNA cleavage and BSA interaction of a mixed-ligand copper(II) complex with taurine Schiff base and 1,10-phenanthroline. Photochem. Photobiol. B 2013;125:56–62.
Search in Google Scholar Back to article
Bi S, Pang B, Zhao T, Wang T, Wang Y, Yan L. Binding characteristics of salbutamol with DNA by spectral methods. Spectrochim. Acta, Part A 2013;111:182–187.
Search in Google Scholar Back to article
Ćoćić D, Jovanović S, Nišavić M, Baskić D, Todorović D, Popović S, Bugarčić ŽD, Petrović B. New dinuclear palladium(II) complexes: Studies of the nucleophilic substitution reactions, DNA/BSA interactions and cytotoxic activity. J. Inorg. Biochem. 2017;175:67–79.
Search in Google Scholar Back to article
Novakova O, Chen H, Vrana O, Rodger A, Sadler PJ, Brabec V. DNA Interactions of Monofunctional Organometallic Ruthenium(II) Antitumor Complexes in Cell-free Media. Biochemistry 2003;42:11544–11554.
Search in Google Scholar Back to article
Rizvi MA, Zaki M, Afzal M, Mane M, Kumar M, Shah BA, Srivastav S, Srikrishna S, Peerzada GM, Tabassum S. Nuclear blebbing of biologically active organoselenium compound towards human cervical cancer cell (HeLa): In vitro DNA/HSA binding, cleavage and cell imaging studies. Eur. J. Med. Chem. 2015;90:876–888.
Search in Google Scholar Back to article
Recio Despaigne AA, Da Silva JG, da Costa PR, dos Santos RG, Beraldo H. ROS-Mediated Cytotoxic Effect of Copper(II) Hydrazone Complexes against Human Glioma Cells. Molecules 2014;19:17202–17220.
Search in Google Scholar Back to article
Dhar S, Nethaji M, Chakravarty AR. Effect of charge transfer bands on the photo-induced DNA cleavage activity of [1-(2-thiazolylazo)-2-naphtholato]copper(II) complexes. J. Inorg. Biochem. 2005;99:805–812.
Search in Google Scholar Back to article
Wang Y, Zhang H, Zhang G, Tao W, Tang S. Interaction of the flavonoid hesperidin with bovine serum albumin: A fluorescence quenching study. J. Lumin. 2007;126:211–218.
Search in Google Scholar Back to article
Johansson JS. Binding of the volatile anesthetic chloroform to albumin demonstrated using tryptophan fluorescence quenching. J. Biol. Chem. 1997;272:17961–17965.
Search in Google Scholar Back to article
Psomas G, Kessissoglou DP. Quinolones and non-steroidal anti-inflammatory drugs interacting with copper(II), nickel(II), cobalt(II) and zinc(II): structural features, biological evaluation and perspectives. Dalton Trans. 2013;42:6252–6276.
Search in Google Scholar Back to article

DNA and BSA-Binding Studies of Dinuclear Palladium(II) Complexes with 1,5-Naphtiridine Bridging Ligands

Abstract

Paradigm

My account