نوع مقاله : مقاله پژوهشی کامل
نویسندگان
1 گروه شیمی، دانشگاه پیام نور، صندوق پستی 4697-19395 تهران، ایران
2 گروه زیست‌شناسی، دانشکده علوم طبیعی، دانشگاه تبریز، تبریز، ایران
چکیده
چکیده
شلات درمانی از دیرباز برای حذف فلزات سمی از بدن مورد استفاده قرار میگرفته است. فلاونوئیدهایی مانند کوئرستین (QUR)، یک آنتی اکسیدان محافظ شناخته شده و بعنوان پاککننده رادیکالهای آزاد، میتوانند به کاتیونهای فلزی متصل شده و از بدن ما در برابر فلزات سمی محافظت کنند. در مطالعه حاضر، از تکنیک‌های طیف‌سنجی ماوراء بنفش-مرئی (UV-vis)، 1HNMR، IR و فلوئورسانس و همچنین اندازه‌گیری‌های ویسکوزیته برای سنتز، مشخصه یابی و مطالعه برهمکنش بین کمپلکس Bi(III)-QUR و DNA تیموس گوساله (ctDNA) در بافر فیزیولوژیکی استفاده شد. فعالیت آنتی اکسیدانی کمپلکس با استفاده از مهار رادیکال آزاد DPPH و ABTS و پتانسیل کاهش آهن (III) مورد ارزیابی قرار گرفت. پس از شلاسیون کاتیون بیسموت، (III)Bi، پتانسیل آنتیاکسیدانی QUR کاهش یافت. در حضور ctDNA، طیف جذب کمپلکس Bi(III)-QUR و شدت فلوئورسانس کمپلکس Bi(III)-QUR افزایش یافت. همچنین با افزودن کمپلکس Bi(III)-QUR، ویسکوزیته نسبی ctDNA افزایش یافت. این یافته‌ها نشان میدهد که کمپلکس Bi (III)-QUR با ctDNA در حالت اتصال به شیار برهم کنش میدهد. پارامترهای ترمودینامیکی (ΔH، ΔS و ΔG) کمپلکس Bi(III)-QUR با ctDNA، و همچنین ثابت اتصال، Ka، و تعداد مکان‌های اتصال (n)، از داده‌های فلوئورسانس ارزیابی شدند، و نتایج نشان داد که اتصال کمپلکس Bi(III)-QUR به ctDNA عمدتا بواسطه نیروهای آبگریز پیش میرود.
کلیدواژه‌ها
- Ndagi, N. Mhlongo, and M.E. Soliman, Metal complexes in cancer therapy – an update from drug design perspective, Drug Des. Devel. Ther. 11 (2017) 599–616.
- H. Thompson and C. Orvig, Metal complexes in medicinal chemistry: new vistas and challenges in drug design, Dalton Trans. 6 (2006) 761–764.
- CA Bruijnincx and P.J. Sadler, New trends for metal complexes with anticancer activity, Curr. Opin. Chem. Biol. 12 (2008)197–206.
- L. Heras, A. Amesty, A. Estevez-Braun and S. Hortelano, Metal complexes of natural product like-compounds with antitumoral activity, AntiCancer Agents Med. Chem. 19 (2019) 48-65.
- Khater, D. Ravishankar, F. Greco and H. MI Osborn, Metal complexes of flavonoids: their synthesis, characterization and enhanced antioxidant and anticancer activities, Future Med. Chem. 11 (2019), 2845–2867.
- Shaghaghi, S. Rashtbari, S. Vejdani, G. Dehghan, A. Jouyban and R. Yekta, Exploring the interactions of a Tb(III)-quercetin complex with serum albumins (HSA and BSA): spectroscopic and molecular docking studies, Luminescence 35 (2020) 512-524.
- Wang, Y. Huang, J.S. Zhang and X.B. Yang, Synthesis, characterization, DNA interaction, and antitumor activities of La(III) complex with Schiff base ligand derived from kaempferol and diethylenetriamine, Bioinorg. Chem. Appl. 2014 (2014) 1-9.
- E.A. Ikeda, E.M. Novak, D.A. Maria, A.S. Velosa, and R.M.S. Pereira, Synthesis, characterization and biological evaluation of Rutin–zinc(II) flavonoid -metal complex, Chem.-Biol. Interact. 239 (2015) 184–191.
- B. Bukhari, S. Memon, M. Mahroof-Tahir and M.I. Bhanger, Synthesis, characterization and antioxidant activity copper–quercetin complex, Spectrochim. Acta A 71 (2009) 1901–1906.
- P. Qadeer, and S. Memon, Synthesis of Cr(III)-morin complex: characterization and antioxidant Study, Sci. World J. 2014 (2014) 1-8.
- M.S. Pereira, N.E.D. Andrades, N. Paulino, A.C.H.F. Sawaya, M.N. Eberlin, M.C. Marcucci, G.M. Favero, E.M. Novak, and S.P. Bydlowski, Synthesis and characterization of a metal complex containing naringin and Cu, and its antioxidant, antimicrobial, anti-inflammatory and tumor cell cytotoxicity, Molecules 12 (2007) 1352-1366.
- A. Farhan, Study on the interaction of copper (II) complex of morin and its antimicrobial effect, Int. J. Chem. Sci. 11(2013) 1247-1255.
- Zhang, J. Guo, N. Zha, and J. Wang, Study of interaction between kaempferol–Eu3+ complex and DNA with the use of the neutral red dye as a fluorescence probe, Sens. Actuators B Chem. 144 (2010) 239–246.
- Liu, and M. Guo, Studies on transition metal-quercetin complexes using electrospray ionization tandem mass spectrometry, Molecules 20 (2015) 8583-8594.
- Zhang, J. Guo, J. Pan, X. Chen and J. Wang, Spectroscopic studies on the interaction of morin–Eu(III) complex with calf thymus DNA, J. Mol. Struct. 923 (2009) 114–119.
- M. Kasprzak, A. Erxleben and J. Ochocki, Properties and applications of flavonoid metal Complexes, J. Name. 00, 1-3 (2013) 1-23.
- Ezzati Nazhad Dolatabadi, A. Mokhtarzadeh, S.M. Ghareghoran, and G. Dehghan, Synthesis, characterization, and antioxidant property of quercetin-Tb(III) complex, Adv. Pharm. Bull. 4 (2014) 101-104.
- M. Bothwell, S.W. Krabbe, and R.S. Mohan, Applications of bismuth(III) compound in organic synthesis. Chemical Society Reviews, 40, 4649-4707.
- Pannequin, S. Kovact, J.P. Tantiongco, R.S. Norton, A. Shulkes, K.J. Barnham, and G.S. Baldwin, A novel effect of Bismuth ions: selective inhibition of the biological activity of glycine-extended gastrin. J. Biol. Chem. 279 (2004) 2453–2460.
- J. Sadler, H. Li, and H. Sun, Coordination chemistry of metals in medicine: target sites for bismuth. Coord. Chem. Rev. 185-186 (1999) 689-709.
- Wang, X. Zhang, J. Lin, J. Chen, Q. Xu, and Z. Guo, DNA-binding property and antitumor activity of bismuth(III) complex with 1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10 tetraazacyclododecane, Dalton Trans. 12 (2003) 2379-2380.
- S. Prasad, L.S. Kumar, S. Chandan, R.M. Naveen Kumar, and H.D. Revanasiddappa, Palladium(II) complexes as biologically potent metallo-drugs: Synthesis, spectral characterization, DNA interaction studies, and antibacterial activity, Spectrochim. Acta A Mol. Biomol. Spectrosc. 107 (2013) 108–116.
- Shaghaghi, G. Dehghan, A. Jouyban, P. Sistani and M. Arvin, Studies of interaction between terbium(III)-deferasirox and double-helix DNA by spectral and electrochemical methods, Spectrochim. Acta A Mol. Biomol. Spectrosc. 120 (2014) 467-472.
- Hanifeh Ahagh, G. Dehghan, M. Mahdavi, M.A. Hosseinpour Feizia, R. Teimuri-Mofrad, E. Payami, M. Mehdipour, and S. Rashtbari, DNA binding ability and cytotoxicity, cell cycle arrest and apoptosis-inducing properties of a benzochromene derivative against K562 human leukemia cells, against K562 human leukemia cells, Nucleos. Nucleot. Nucl. 2021,40, 732-753.
- Khosravifar, G. Dehghan, S.K. Bidoki and M. Mahdavi, DNA-binding activity and cytotoxic and cell-cycle arrest properties of some new coumarin derivatives: a multispectral and computational investigation, Luminescence 35 (2020) 98-106.
- H. Hegde, S.N. Prashanth, and J. Seetharamappa, Interaction of antioxidant flavonoids with calf thymus DNA analyzed by spectroscopic and electrochemical methods, J. Pharm. Biomed. Anal. 63 (2012) 40–46.
- Daravath, M.P. Kumar, A. Rambabu, N. Vamsikrishna and G.N. Shivaraj, Design, synthesis, spectral characterization, DNA interaction and biological activity studies of copper(II), cobalt(II) and nickel(II) complexes of 6-amino benzothiazole derivatives, J. Mol. Struct. 1144 (2017) 147-158.
- Kumar, S. Dasari and A.K. Patra, Ruthenium(II) complexes of saccharin with dipyridoquinoxaline and dipyridophenazine: Structures, biological interactions, and photo induced DNA damage activity, Eur. J. Med. Chem.136 (2017) 52-62.
- Dehghan, J. Ezzati Nazhad Dolatabadi, A. Jouyban, K. Asadpour Zeynali, S.M. Ahmadi and S. Kashanian, Spectroscopic studies on the interaction of quercetin–Tb(III) complex with calf thymus DNA. DNA. Cell. Biol. 30 (2011) 195–201.
- M. Ahmadi, G. Dehghan, M.A. Hosseinpour Feizi, J. Ezzati Nazhad Dolatabadi, and S. Kashanian, Preparation, characterization, and DNA binding studies of water-soluble quercetin–molybdenum(VI) complex. DNA. Cell. Biol. 30 (2011) 517-523.
- Wettasinghe and F. Shahidi, Scavenging of reactive oxygen species and DPPH free radicals by extracts of borage and evening primrose meals. Food Chem. 70 (2000) 17-26.
- F.F. Benzie and J.J. Strain, Ferric reducing/ antioxidant power assay: direct measure of total antioxidant activity of biological fluids and modified version for simultaneous measurement of total antioxidant power and ascorbic acid concentration. Meth. Enzymol. 299 (1999) 15–27.
- C. Pennycooke, S. Cox, and C. Stushnoff, Relationship of cold acclimation, total phenolic content and antioxidant capacity with chilling tolerance in petunia (Petunia x hybrida). Environ. Exp. Bot. 53 (2005) 225-232.
- Shaghaghi, J.L.Manzoori, and A. Jouyban, Determination of total phenols in tea infusions, tomato, and apple juice by terbium sensitized fluorescence method as an alternative approach to the Folin–Ciocalteu spectrophotometric method, Food Chem. 108 (2008) 695-701.
- Zhou, L.F. Wang, J.Y. Wang, and N. Tang, Synthesis, characterization, antioxidative and antitumor activities of solid quercetin rare earth(III) complexes. J. Inorg. Biochem. 83 (2001) 41-48.
- Pekal, M. Biesaga, and K. Pyrzynska, Interaction of quercetin with copper ions: complexation, oxidation, and reactivity towards radicals. Biometals 24 (2011) 41–49.
- Dehghan, A. Shafiee, M.H. Ghahremani, S.K. Ardestani, and M. Abdollahi, Antioxidant potential of various extracts from ferula szovitsiana in relation to their phenolic contents, Pharm. Biol. 45(2007) 1–9.
- Kyropoulou, C.P. Raptopoulou, V. Psycharis, and G. Psomas, Ni(II) complexes with non-steroidal anti-inflammatory drug diclofenac: Structure and interaction with DNA and albumins, Polyhedron 61 (2013) 126–136.
- Karami, Z. Mehri Lighvan, M. Dehdashti Jahromi, J. Lipkowski, and A.A. Momtazi-Borojeni, Synthesis, electronic structure and molecular docking of new organometallic palladium (II) complexes with intercalator ligands: The influence of bridged ligands on enhanced DNA/serum protein binding and in vitro antitumoral activity, J. Organomet. Chem. 827 (2017) 1–14.
- Rashtbari and G. Dehghan, Biodegradation of malachite green by a novel laccase-mimicking multicopper BSA-Cu complex: Performance optimization, intermediates identification, and artificial neural network modeling, J. Hazard. Mater. 406 (2021), 124340.
- Bouroumand, F. Marshall, and F. Khazali Determining the Amount of Metronidazole Drug in Blood and Urine Samples with the help of PbS Sensor functionalized with gelatin as a fluorescence-enhanced probe, Iranian Journal of Analytical Chemistry, Iran. J. Anal. Chem.
7(2020) 47-56. - Wolfe, G.H. Shimer Jr and T. Meehan, Polycyclic Aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochem. 26 (1987) 6392-6396.
- D. Ross and S. Subramanian, Thermodynamics of protein association reactions: forces contributing to stability. Biochem. 20 (1981) 3096-3102.
- Aki and M. Yamamoto, Thermodynamics of the binding of phenothiazines to human plasma, human serum albumin and α1-acid glycoprotein: A calorimetric study. J. Pharm. Pharmacol. 41 (1989) 674-679.
- L. Eichhorn and Y. Ae Shin, Interaction of metal ions with polynucleotides and related compounds. XII. The relative effect of various metal ions on DNA helicity, J. Am. Chem. Soc. 90 (1968) 7323–7328.
- Liu, K.A. Meadows, and D.R. McMillin, DNA-binding studies of Cu( bcp)2+ and Cu( dmp)2+: DNA elongation without intercalation of Cu(bcp)2+, J. Am. Chem. Soc. 115 (1993) 6699-6704.
)