Luận án Nghiên cứu tổng hợp, xác định cấu trúc và thăm dò hoạt tính sinh học của một số phức chất pt(ii), pd(ii) với phối tử bazơ schiff

ế đẩy và hút điện tử trong vòng thơm (ngoại trừ phức có nhóm thế hút điện tử F). Phức chất cấu hình (R) có hoạt tính tốt hơn cấu hình (S). Phức chất Pd(II) có hoạt tính và phức chất Pt(II) không có hoạt tính Phức chất có nguyên tử F trong vòng thơm có hoạt tính tốt nhất trong dãy phối tử dạng 2 càng NO Bảng 3.27. Bảng tổng kết các phức chất Pt(II), Pd(II) với phối tử bazơ Schiff 4 càng và 2 càng T T Viết tắt Tên phối tử Công thức cấu tạo 1 [Pt(spd)] 121a N,N'-bis(salicylidene)-1,2- phenylendiamine 134 2 [Pd(spd)] 121b N,N'-bis(salicylidene)-1,2- phenylendiamine 3 [Pt(cis-scd)] 122a cis-N,N'-bis(salicylidene)-1,2- cyclohexanediamine 4 [Pd(cis-scd)] 122b cis-N,N'-bis(salicylidene)-1,2- cyclohexanediamine 5 [Pt(trans-scd)] 122c trans-N,N'-bis(salicylidene)-1, 2-cyclohexanediamine 6 [Pd(trans-scd)] 122d trans-N,N'-bis(salicylidene)-1, 2-cyclohexanediamine 7 [Pt(sed)] 123a N,N'-bis(salicylidene)-1,2- ethylenediamine 8 [Pd(sed)] 123b N,N'-bis(salicylidene)-1,2- ethylenediamine 9 [Pt(5msed)] 124a N,N'-bis(5-methoxy- salicylidene)-1,2- ethylenediamine 10 [Pd(5msed)] 124b N,N'-bis(5-methoxy- salicylidene)-1,2- ethylenediamine 11 [Pt(3tbsed)] 125a N,N'-bis(3-tert-butyl- salicylidene )-1,2- ethylenediamine 135 12 [Pd(3tbsed)] 125b N,N'-bis(3-tert-butyl- salicylidene )-1,2- ethylenediamine 13 [Pt(5tbsed) 126a N,N'-bis(5-tert-butyl- salicylidene )-1,2- ethylenediamine 14 [Pd(5tbsed)] 126b N,N'-bis(5-tert-butyl- salicylidene)-1,2- ethylenediamine 15 [Pd(3,5tbsed)] 127 N,N'-bis(3,5-tert- butylsalicylidene)-1,2- ethylenediamine 16 [Pt(5Clsed)] 128a N,N'-bis(5-chloro- salicylidene)-1,2- ethylenediamine 17 [Pd(5Clsed)] 128b N,N'-bis(5-chloro- salicylidene)-1,2- ethylenediamine 18 [Pt(5Brsed)] 129a N,N'-bis(5-bromo- salicylidene)-1, 2- ethylenediamine 19 [Pd(5Brsed)] 129b N,N'-bis(5-bromo- salicylidene)-1, 2- ethylenediamine 20 [Pt(5Ised)] 130a N,N'-bis(5-iodo-salicylidene)- 1,2-ethylenediamine 21 [Pd(5Ised)] 130b N,N'-bis(5-iodo-salicylidene)- 1,2-ethylenediamine 22 [Pd(5Fsed)] 131 N,N'-bis(5-fluoro-salicylidene)- 1, 2-ethylenediamine 136 23 [Pt(R-spa)2] 132a (R)-N-salicylidene-1- phenylethyamine 24 [Pd(R-spa)2] 132b (R)-N-salicylidene-1- phenylethylamine 25 [Pd(S-spa)2] 132c (S)-N-salicylidene-1- phenylethylamine 26 [Pd(S-5mspa)2] 133 (S)-N-5- methoxy-salicylidene- 1-phenylethylamine 27 [Pd(R-5tbspa)2] 134a (R)-N-5-tert-butyl-salicylidene- 1-phenylethylamine 28 [Pd(S-5tbspa)2] 134b (S)-N-5-tert-butyl-salicylidene- 1-phenylethylamine 137 29 [Pd(R-5Clspa)2] 135a (R)-N-5-chloro-salicylidene-1- phenylethylamine 30 [Pd(S-5Clspa)2] 135b (S)-N-5-chloro-salicylidene-1- phenylethylamine 31 [Pt(R-5Brspa)2] 136a (R)-N-5-bromo-salicylidene-1- phenylethylamine 32 [Pd(R-5Brspa)2] 136b (R)-N-5-bromo-salicylidene-1- phenylethylamine 33 [Pd(S-5Brspa)2] 136c (S)-N-5-bromo-salicylidene-1- phenylethylamine 34 [Pd(R-5Ispa)2] 137a (R)-N-5-iodo-salicylidene-1- phenylethylamine 138 35 [Pd(S-5Ispa)2] 137b (S)-N-5-iodo-salicylidene-1- phenylethylamine 36 [Pt(R-5Fspa)2] 138a (R)-N-5- fluoro-salicylidene-1- phenylethylamine 37 [Pd(R-5Fspa)2] 138b (R)-N-5- fluoro-salicylidene-1- phenylethylamine 38 [Pd(S-5Fspa)2] 138c (S)-N-5- fluoro-salicylidene-1- phenylethylamine 139 KẾT LUẬN Luận án đã nghiên cứu tổng hợp 71 chất và thăm dò hoạt tính sinh học của các phức chất. Cấu trúc của các chất được chứng minh bằng các phương pháp phổ IR, ESI-MS, 1H-NMR, 13C-NMR và giá trị alpha D (đối với phức chất với phối tử 2 càng). 1. Đã tổng hợp 8 salicylaldehyde có các nhóm thế tại vị trí R3, R5khác nhau bằng phản ứng Reimer–Tiemann. 2. Đã tổng hợp và xác định cấu trúc của 25 phối tử bazơ Schiff . 3. Đã tổng hợp và xác định cấu trúc 38 phức chất Pt(II) và Pd(II) với phối tử bazơ Schiff 4 càng và phối tử 2 càng . 4. Đã đánh giá hoạt tính gây độc tế bào ung thư của 24 phức chất trên 4 dòng tế bào ung thư: Ung thư biểu mô (KB), ung thư gan (Hep-G2), ung thư phổi (Lu), ung thư vú (MCF-7). Kết quả cho thấy có 10/24 phức chất thể hiện hoạt tính gây độc tế bào ung thư ở các mức độ khác nhau, có 4/10 phức chất có hoạt tính < 20 µM (123a, 126a, 138b, 138c). Đặc biệt, phức chất 123a giá trịIC50 đạt 3,14 µM (KB), 3,57 µM (Hep-G2) và giá trị này gần bằng so với chất chuẩn ellipticine [IC50 đạt 2,03 µM (KB) và 2,47 µM (Hep-G2)]. Phức chất [Pd(R-5Fspa)2] 138b có có giá trị IC50 trên 4 dòng tế bào ung thư như sau: giá trịIC50 đạt 11,10 µM (KB), 6,69 µM (Hep-G2), 8,04 (Lu), 16,64 µM (MCF-7). - Phức chất của Pd(II) cấu hình (R) có hoạt tính kháng ung thư tốt hơn cấu hình (S). Phức chất của Pt(II) không có hoạt tính kháng ung thư (Hệ 2 càng). - Phức chất của Pd(II) không có hoạt tính kháng ung thư (Hệ 4 càng). 5. Đã thử hoạt tính kháng vi sinh vật của 2 phối tử 114a, 114b và 6 phức chất 121b, 122b, 122d, 123b, 132b, 132c trên các dòng vi sinh vật kiểm định Gram (+): Staphylococcus aureus, Bacillus subtilis, Lactobacillus fermentum; Gram (-): Salmonella enterica, Escherichia coli, Pseudomonas aeruginosa và nấm: candila albican. Kết quả cho thấy các mẫu đều không có hoạt tính kháng vi sinh vật. Như vậy, các kết quả nghiên cứu đã góp phần cung cấp dữ kiện cho việc nghiên cứu mối quan hệ giữa cấu trúc và hoạt tính sinh học của các phức chất Pt(II), Pd(II) với các phối tử hữu cơ bazơ Schiff 4 càng và 2 càng. 140 NHỮNG ĐÓNG GÓP MỚI CỦA LUẬN ÁN Đã tổng hợp được 25 phối tử bazơ Schiff nhờ phản ứng ngưng tụ từ salicylaldehyde có các nhóm thế tại vị trí R3, R5 khác nhau với hợp chất diamine bậc 1 là: 1,2-phenylendiamine, cis- và trans-1,2-cyclohexanediamine, 1,2-ethylene diamine và với monoamine bậc 1 là: (R)- và (S)-1-phenylethylamine. Xác định cấu trúc phối tử bằng các phương pháp phổ IR, ESI-MS, 1H-NMR, 13C-NMR. Lần đầu tiên ở Việt Nam đã tổng hợp được 38 phức chất Pt(II), Pd(II) với phối tử bazơ Schiff dạng 4 càng N2O2 và 2 càng NO. Xác định cấu trúc bằng các phương pháp phổ IR, ESI-MS, 1H-NMR, 13C-NMR, HSQC, HMBC và đo alpha D (đo cho phức chất với phối tử dạng 2 càng). Đã thử hoạt tính gây độc tế bào của phức chất trên 4 dòng tế bào ung thư. Kết quả cho thấy có 10 phức chất có hoạt tính kháng lại các dòng tế bào ung thư ở các mức độ khác nhau, trong đó có 4/10 phức chất có hoạt tính <20 µM và đặc biệt có 2 phức chất có hoạt tính tốt, đó là: Phức chất dạng 4 càng [Pt(sed)] 123a (Phức chất Pt(II) với phối tử N,N'-bis (salicylidene)-1,2-ethylenediamine): Có hoạt tính kháng ung thư, giá trị IC50 đạt 3,14 µM (KB), 3,57 µM (Hep-G2) và giá trị này gần bằng so với chất chuẩn ellipticine (IC50 đạt 2,03 µM (KB) và 2,47 µM (Hep-G2)). Phức chất dạng 2 càng [Pd(R-5Fspa)2] 138b (Phức chất Pd(II) với phối tử (R)-N-5- fluoro-salicylidene-1-phenylethylamine): Có hoạt tính kháng ung thư có giá trị IC50 đạt 11,10 µM (KB), 6,69 µM (Hep-G2), 8,04 µM (Lu). Riêng đối với dòng tế bào ung thư vú (MCF-7) có giá trị IC50 đạt 16,64 µM, thấp hơn các nhà khoa học trên thế giới công bố cho kết quả IC50 = 30,26–48,29 µM (MCF-7). Các kết quả nghiên cứu đã góp phần cung cấp số dữ liệu cho việc nghiên cứu mối quan hệ giữa cấu trúc và hoạt tính sinh học của các phức chất Pt(II), Pd(II) với các phối tử hữu cơ bazơ Schiff 4 càng và 2 càng. 141 CÁC CÔNG TRÌNH CÔNG BỐ LIÊN QUAN ĐẾN ĐỀ TÀI LUẬN ÁN 1. Lam Quang Hai, Nguyen Van Tuyen, Nguyen Quang Trung, Nguyen Thi Bich Huong, Dang Thi Tuyet Anh. Synthesis and structural characterization of palladium(II) complexes with tetradentate N2O2 and bidentate NO-donor salicylaldehyde Schiff base ligands. Vietnam Journal of Science and Technology, Issue 10.2017, Volume 55 (Number 5B), 86–93. 2. Lâm Quang Hải, Nguyến Văn Tuyến, Nguyễn Quang Trung. Tổng hợp, đặc trưng và độc tính tế bào của phức chất Pt(II) với phối tử bazơ Schiff dạng salen, Tạp chí Hóa học, 12.2017, 55 (5E34), 206–211. 3. Lâm Quang Hải, Nguyễn Văn Tuyến, Nguyễn Quang Trung, Nguyễn Thị Bích Hường. Tổng hợp, nghiên cứu cấu trúc và độc tính tế bào của phức chất Pd(II) với phối tử bazơ Schiff hai càng N,O: (S)-N-5-methoxy-salicylidene-1- phenylethylamine và (R)-, (S)-N-5-iodo-salicylidene-1-phenylethylamine., Tạp chí Hóa học, 12.2017, 55 (5E34), 202–205. 4. Lâm Quang Hải, Nguyễn Văn Tuyến, Nguyễn Quang Trung. Tổng hợp, đặc trưng và độc tính tế bào của phức chất Pd(II) với phối tử bazơ Schiff (R)-,(S)-N- 5-chloro-salicylidene-1-phenylethylamine và (R)-, (S)-N-5-bromo-salicylidene- 1-phenylethylamine, Tạp chí Hóa học, 12.2017, 55 (5E34), 235–239. 5. Lâm Quang Hải, Nguyễn Văn Tuyến, Nguyễn Quang Trung, Nguyễn Thị Bích Hường, Tổng hợp, đặc trưng và độc tính tế bào của phức chất Pt(II), Pd(II) với phối tử bazơ Schiff (R)-, (S)-N-5-flouro-salicylidene-1-phenylethylamine. Tạp chí Phân tích Hóa lý và Sinh học, 2017, 22 (4), 108–114. 6. Lâm Quang Hải, Nguyễn Văn Tuyến, Nguyễn Quốc Tuấn, Nguyễn Quang Trung. Tổng hợp, đặc trưng hóa lý của phức Pd(II) với các phối tử hữu cơ bazơ Schiff dạng salen, 7.2017, 6 (3), 133–138. 7. Lâm Quang Hải, P.T. Phương Nam, Nguyễn Văn Tuyến, Nguyễn Quốc Tuấn, Nguyễn Quang Trung. Tổng hợp, đặc trưng và độc tính tế bào của phức chất Palladium(II) với phối tử bazơ Schiff hai càng dạng NO quang hoạt, Tạp chí Hóa học, 6.2017, 55 (3E12), 17–21. 8. Nguyễn Quang Trung, Lâm Quang Hải, P.T. Phương Nam, Nguyễn Văn Tuyến. Nghiên cứu tổng hợp, xác định đặc trưng và độc tính tế bào của phức Pd(II) và Pt(II) với phối tử bazơ Schiff cis-N.N’bis(salicylidene) và -trans-1,2- cyclohexanediamine, Tạp chí Hóa học, 8.2017, 55 (4E23), 7–11. 9. Nguyễn Quang Trung, Lâm Quang Hải, Nguyễn Văn Tuyến. Tổng hợp, đặc trưng và hoạt tính kháng ung thư in vitro của phức chất Pt(II) với một số bazơ Schiff dạng salen, Tạp chí Hóa học, 12.2016, 54 (6E2), 219–222. 142 TÀI LIỆU THAM KHẢO TIẾNG VIỆT [1] Trần Thị Đà, Nguyễn Hữu Đĩnh. 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