(Luận văn thạc sĩ) nghiên cứu tổng hợp, xác định cấu trúc và thăm dò hoạt tính ức chế tế bào ung thư của phức ion cu2+, zn2+, cd2+ với salicylaldehyde n(4) morpholinylthiosemicarbazone​

cấu trúc phân tử đề nghị giả định sau: HL1 phối trí với ion trung tâm thông qua Cacbon (N=C), nitơ (C=N) oxi (C-O) lưu huỳnh (C=S), với dung lượng phối trí phức chất ZnL1, CdL1 (thông qua Nitơ lưu huỳnh) CuL1 [thông qua cacbon (N=C), oxi (C-O) lưu huỳnh (C=S)]: 47 Thăm dị hoạt tính sinh học phối tử HL1 ba phức chất dòng tế bào Hep-G2 (Tế bào ung thư gan), A549 (Tế bào ung thư phổi).Trong CdL1 CuL1 thể hoạt tính tốt dịng tế bào Nếu có điều kiện thuận lợi thời gian, kinh phí sở vật chất, kết kinh nghiệm có được, chúng tơi sẽ: - Nghiên cứu đơn tinh thể HL1 XRD để có sở xác định xác cấu hình E/Z HL1 cis/trans-MHL - Mở rô ̣ng thăm dò khả gây đô ̣c tế bào với nhiề u dòng ung thư khác - Mở rộng ứng dụng HL MHL nghiên cứu điện hóa phân tích định lượng 48 TÀI LIỆU THAM KHẢO [1] Rapheal P.F (2006), Diversity in structural and spectral chacracteristics of some transition metal complexes derived from aldehyde based thiosemicarbazone ligands, Department of Applied Chemistry Cochin University of Science and Technology, India [2] S Poorhaji, M Pordel, S Ramezani (2016), New heterocyclic green, blue and orange dyes from indazole: Synthesis, tautomerism, alkylation studies, spectroscopic characterization [3] A.R Hajipour, S Ghorbani, M Karimzadeh, S Jajarmi, A.N Chermahini (2016), A DFT approach for simple and solvent assisted-proton movement: Biurea as a case of study, Computational and Theoretical Chemistry 1084, pp 67-74 [4] G Marchand, P Giraudeau, Z.R Chen, M Elhabiri, O Siri, D Jacquemin (2016), Understanding the tautomerism in azacalixphyrins Physical Chemistry Chemical Physics 18, pp 9608-9615 [5] A Schade, K Schreiter, T Ruffer, H Lang, S Spange (2016), Interactions of Enolizable Barbiturate Dyes Chemistry–A European Journal 22, pp 5734-5748 [6]C H Gu, H Li, R.B Gandhi, K Raghavan (2004) ,Grouping solvents by statistical analysis of solvent property parameters: implication to polymorph screening, International Journal of Pharmaceutics, 283, pp 117-125 [7] Bingham, Alistair G., et al (1987), Synthetic, spectroscopic, and X-ray crystallographic studies on binuclear copper (II) complexes with a tridentate NNSbonding 2-formylpyridine thiosemicarbazone ligand The characterization of both neutral and deprotonated co-ordinated ligand structures, Journal of the Chemical Society, Dalton Transactions 3, pp 493-499 [8] Giorgio Pelosi (2010), Thiosemicarbazone Metal Complexes: From Structure to Activity, The Open Crystallography Journal, 3, pp 16-28 [9] Tarlok S Lobana, Rekha Sharma, Gagandeep Bawa, Sonia Khanna (2009), Bonding and structure trends of thiosemicarbazone derivatives of metals—An overview, Coordination Chemistry Reviews, Vol 253, 7–8, pp 977-1055 [10] Y Khuhawar, Z.P Memon, S.N Lanjwani (1995), HPLC determination of copper(II), cobalt(II) and iron(II) in pharmaceutical preparations using 2-acetylpyridine- 49 4-phenyl-3-thiosemicarbazone derivatizing agent, Chromatographia, Vol 41,3–4, pp 236–23741, 236 [11] P.C Okafor, E.E Ebenso, UJ Ekpe (2004), Inhibition of the acid corrosion of aluminium by some derivatives of thiosemicarbazone, Bulletin of the Chemical Society of Ethiopia, 18(2), pp 181-192 [12] Kang, Iou-Jiun, et al (2011), Isatin-β-thiosemicarbazones as potent herpes simplex virus inhibitors, Bioorganic & medicinal chemistry, pp 1948-1952 [13] Karakỹỗỹk-yidoan, Ayegỹl, et al (2011), Novel platinum (II) and palladium (II) complexes of thiosemicarbazones derived from 5-substitutedthiophene-2- carboxaldehydes and their antiviral and cytotoxic activities, European journal of medicinal chemistry 46.11, pp 5616-5624 [14] Shebl, M., H S Seleem, and B A El-Shetar (2010), Ligational behavior of thiosemicarbazone, semicarbazone and thiocarbohydrazone ligands towards VO (IV), Ce (III), Th (IV) and UO (VI) ions: synthesis, structural characterization and biological studies, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 75.1, pp 428-436 [15] Altun, A., M Kumru, and A Dimoglo (2001), The role of conformational and electronic parameters of thiosemicarbazone and thiosemicarbazide derivatives for their dermal toxicity, Journal of Molecular Structure: THEOCHEM 572.1, pp 121-134 [16] Dilworth, Jonathan R., and Rebekka Hueting (2012), Metal complexes of thiosemicarbazones for imaging and therapy, Inorganica Chimica Acta 389, pp 3-15 [17] Liu, Mao-Chin, Tai-Shun Lin, and Alan C Sartorelli (1995), Chemical and Biological Properties of Cytotoxic α-(N)-Heterocyclic Carboxaldehyde Thiosemicarbazones, Progress in medicinal chemistry 32, pp 1-35 [18] Sakirigui, Amoussatou, et al (2012), Selective trypanocide activity of some substituted thiosemicarbazones of citral from benin Cymbopogon citratus essential oil and their toxicity against Artemia salina Leach, International Journal of Research and Reviews in Applied Sciences 12.3 [19]Dilworth, Jonathan R., and Rebekka Hueting (2012), Metal complexes of thiosemicarbazones for imaging and therapy, Inorganica Chimica Acta 389, pp 3-15 50 [20] Fatondji, Houssou Raymond, et al (2013), Structure–activity relationship study of thiosemicarbazones on an African trypanosome: Trypanosoma brucei brucei, Medicinal Chemistry Research 22.5, pp 2151-2162 [21]Serda, Maciej, et al (2012), Investigation of the biological properties of (hetero) aromatic thiosemicarbazones, Molecules 17.11, pp.13483-13502 [22]Pingaew, Ratchanok, Supaluk Prachayasittikul, and Somsak Ruchirawat (2010), Synthesis, cytotoxic and antimalarial activities of benzoyl thiosemicarbazone analogs of isoquinoline and related compounds, Molecules 15.2, pp 988-996 [23] Bingham, Alistair G., et al (1987), Synthetic, spectroscopic, and X-ray crystallographic studies on binuclear copper (II) complexes with a tridentate NNSbonding 2-formylpyridine thiosemicarbazone ligand The characterization of both neutral and deprotonated co-ordinated ligand structures, Journal of the Chemical Society, Dalton Transactions 3, pp 493-499 [24] Makavana, Madhuresh, and Sangita Sharma (2016), Ultrasonic, optical and IR studies of binary mixtures of morpholine with some aromatic hydrocarbons at T=(303.15, 308.15 and 313.15) K, Journal of Molecular Liquids 222, pp 535-548 [25] Ghosh, Priya, Manash J Deka, and Anil K Saikia (2016), Lewis acid mediated intramolecular C–O bond formation of alkanol-epoxide leading to substituted morpholine and 1, 4-oxazepane derivatives: total synthesis of (±)–Viloxazine, Tetrahedron 72.5, pp 690-698 [26] Bacher, Felix, et al (2015), Strong effect of copper (II) coordination on antiproliferative activity of thiosemicarbazone–piperazine and thiosemicarbazone– morpholine hybrids, Dalton transactions 44.19, pp 9071-9090 [27] Shi, Hai-Bo, et al (2016), Synthesis of 5-acetyl-2-arylamino-4-methylthiazole thiosemicarbazones under microwave irradiation and their in vitro anticancer activity, Journal of Chemical Research 40.2, pp 67-72 [28] lan A Cree (ed.), Cancer Cell Culture: Methods and Protocols, Second Edition, Methods in Molecular Biology, vol 731, DOI 10.1007/978-1-61779-080-5_20, @)j Springer Science+Business Media, LLC 2011 [29] Mosman, T (1983) Rapid colorimetrie assay for cellular growth and survival: application to proliferation and cytotoxicity assay J Immunol Method., 65, 55-63 51 [30] Xang, L„ Tu, Ủ., Zha0, Z., Cui, J, (2017) Cytotoxicity and apoptosis induced by mixed mycotoxins (T-2 and HT-2 toxin) on primary hepatocytes of broilers ¿ wiro Toxicon 129, 1-10 [31] Zhang, J., Ma, L., Wu, Z-F., Yu, S-L., Wang, L., Ye, W-C., Zhang, Q-W., Yin, ZQ (2017) Cytotoxic and apoptosis-inducing activity of C21 steroids from the roots of Cynanchum airafum Steroid [32] D Kovala-Demertzi, M A Demertzis, J R Miller, C Papadopoulou, C Dodorou, and G Filousis Platinum(II) complexes with 2-acetyl pyridine thiosemicarbazone: Synthesis, crystal structure, spectral properties, antimicrobial and antitumour activity, J Inorg Biochem, 2001, 86 (2-3), pp 555–563 [33] M Jagadeesh, M Lavanya, S K Kalangi, Y Sarala, C Ramachandraiah, and A Varada Reddy Spectroscopic characterization, antioxidant and antitumour studies of novel bromo substituted thiosemicarbazone and its copper(II), nickel(II) and palladium(II) complexes, Spectrochim Acta - Part A Mol Biomol Spectrosc, 2015, 135, pp 180–184 [34] M Jagadeesh, S K Kalangi, L Sivarama Krishna, and A V Reddy Halosubstituted thiosemicarbazones and their copper(II), nickel(II) complexes: Detailed spectroscopic characterization and study of antitumour activity against HepG2 human hepatoblastoma cells, Spectrochim Acta - Part A Mol Biomol Spectrosc, 2014, 118, pp 552–556 [35] M Adams, C De Kock, P J Smith, K Chibale, and G S Smith Synthesis, characterization and antiplasmodial evaluation of cyclopalladated thiosemicarbazone complexes, J Organomet Chem, 2013, 736, pp 19–26 [36] Jonathan R Dilworth, Rebekka Hueting Metal complexes of thiosemicarbazones for imaging and therapy, Inorganica Chimica Acta, 2012, 389, pp 315 52 PHỤ LỤC Hình 3.14 Phổ 13C-NMR CuL1 53 Hình 3.15 Phổ 1H-NMR CuL1 54 Hình 3.16 Phổ 13C-NMR CdL1 55 Hình 3.17 Phổ 1H-NMR CdL1 56 ...4 Thăm dị hoạt tính sinh học phối tử HL1 ba phức chất dòng tế bào Hep-G2 (Tế bào ung thư gan), A549 (Tế bào ung thư phổi).Trong CdL1 CuL1 thể hoạt tính tốt dịng tế bào Nếu có điều... Nghiên cứu đơn tinh thể HL1 XRD để có sở xác định xác cấu hình E/Z HL1 cis/trans-MHL - Mở rô ̣ng thăm dò khả gây đô ̣c tế bào với nhiề u dòng ung thư khác - Mở rộng ứng dụng HL MHL nghiên. .. ứng dụng HL MHL nghiên cứu điện hóa phân tích định lượng 48 TÀI LIỆU THAM KHẢO [1] Rapheal P.F (2006), Diversity in structural and spectral chacracteristics of some transition metal complexes derived