BỘ GIÁO DỤC VÀ ĐÀO TẠO VIỆN HÀN LÂM KHOA HỌC VÀ CÔNG NGHỆ VIỆT NAM HỌC VIỆN KHOA HỌC VÀ CÔNG NGHỆ - LÂM QUANG HẢI NGHIÊN CỨU TỔNG HỢP, XÁC ĐỊNH CẤU TRÚC VÀ THĂM DỊ HOẠT TÍNH SINH HỌC CỦA MỘT SỐ PHỨC CHẤT Pt(II), Pd(II) VỚI PHỐI TỬ BAZƠ SCHIFF LUẬN ÁN TIẾN SỸ HÓA HỌC HÀ NỘI 2017 VIỆN HÀN LÂM KHOA HỌC VÀ CÔNG NGHỆ VIỆT NAM HỌC VIỆN KHOA HỌC VÀ CÔNG NGHỆ …… ….***………… LÂM QUANG HẢI 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 LUẬN ÁN TIẾN SỸ HĨA HỌC Chun ngành: Hóa Hữu Mã số: 62.44.01.14 Người Hưóng dẫn Khoa học: GS.TS NGUYỄN VĂN TUYẾN TS NGUYỄN QUANG TRUNG HÀ NỘI 2017 LỜI CAM ĐOAN Các kết trình bày luận án cơng trình nghiên cứu riêng tơi Các số liệu kết luận án trung thực chưa cơng bố cơng trình khác Tồn thơng tin trích dẫn luận án rõ nguồn gốc xuất xứ Tôi xin chịu trách nhiệm với lời cam đoan Hà Nội, ngày 12 tháng 12 năm 2017 Tác giả luận án NCS Lâm Quang Hải b LỜI CẢM ƠN Luận án hồn thành Viện Hóa học - Viện Hàn lâm Khoa học & Công nghệ Việt Nam Tơi xin bày tỏ lòng biết ơn sâu sắc, cảm phục, kính trọng đến thầy hướng dẫn khoa học GS.TS Nguyễn Văn Tuyến, TS Nguyễn Quang Trung, người thầy tận tâm hướng dẫn khoa học, động viên, khích lệ, đạo, tạo điều kiện thuận lợi cho suốt thời gian thực hiện, hoàn thành luận án thủ tục để bảo vệ luận án Tôi xin chân thành cảm ơn đến: - GS.TS Nguyễn Văn Tuyến–Viện trưởng, GS.TSKH Trần Văn Sung Tổng biên tập tạp chí Hóa học, ThS Đặng Vũ Lương, Hội đồng Khoa học, Phòng Quản lý Tổng hợp, Phòng Hóa dược, Phòng Tổng hợp Hữu cơ, Trung tâm phân tích phổ thầy giáo, nhà khoa học Viện Hóa học giúp đỡ tơi thực hồn thành luận án; - Ban lãnh đạo, Phòng Đào tạo Nghiên cứu Khoa học Học viện Khoa học Công nghệ, đào tạo, tạo điều kiện thuận lợi giúp đỡ tơi hồn thành thủ tục suốt thời gian bảo vệ luận án cấp; - Tôi xin cám ơn đến 50 thầy/cô giáo, nhà khoa học trường Đại học, Viện nghiên cứu nước đọc viết nhận xét tóm tắt luận án gửi Học Viện; - Th.S Nghiêm Thùy Lan – Chủ tịch Cơng đồn Tập đồn Dầu khí QG Việt Nam định hỗ trợ phần nhỏ kinh phí; - TS Từ Thành Nghĩa–Tổng giám đốc, TSKH Lâm Quang Chiến–Ngun Phó Tổng giám đốc, ơng Lê Quang Mẫn–Trưởng phòng Nhân sự, Xí nghiệp Liên doanh Việt Nga–Vietsovpetro; ông Trần Văn Thường–Giám đốc, ông Nguyễn Trọng Dương–Trưởng phòng Nhân sự, Xí nghiệp Khai thác Dầu khí – OPGE; Trong q trình nghiên cứu Hà Nội, tơi nhận nhiều động viên, giúp đỡ quý báu thầy cô, nhà khoa học anh chị Nghiên cứu sinh, bạn bè gần xa gia đình Luận án q tinh thần, tơi xin kính dâng đến cha mẹ già, gia đình bé nhỏ với tất lòng biết ơn, yêu thương trân trọng Hà Nội, ngày 12 tháng 12 năm 2017 Tác giả luận án NCS LÂM QUANG HẢI c MỤC LỤC LỜI CAM ĐOAN - b DANH MỤC CÁC KÝ HIỆU, CHỮ VIẾT TẮT - f DANH MỤC BẢNG k DANH MỤC SƠ ĐỒ - m DANH MỤC HÌNH - n MỞ ĐẦU - CHƯƠNG TỔNG QUAN - 1.1 Phối tử hữu bazơ Schiff, phức chất kim loại M(II) ứng dụng - 1.2 Nghiên cứu tổng hợp, cấu trúc hoạt tính sinh học phức chất kim loại M(II) với phối tử bazơ Schiff dạng N2O2 1.3 Nghiên cứu tổng hợp, cấu trúc hoạt tính sinh học phức chất M(II) với phối tử bazơ Schiff dạng NO 11 1.4 Tổng quan phức chất Pt(II) ứng dụng điều trị bệnh ung thư - 21 1.5 Tổng quan nghiên cứu phức chất Việt Nam 23 CHƯƠNG THỰC NGHIỆM 26 2.1 Các phương pháp nghiên cứu - 26 2.1.1 Phương pháp tổng hợp tinh chế sản phẩm 26 2.1.2 Phương pháp xác định cấu trúc 26 2.1.3 Phương pháp thử hoạt tính sinh học - 26 2.2 Kỹ thuật thực nghiệm 29 2.3 Tổng hợp salicylaldehyde có nhóm R3, R5 (phản ứng Reimer– Tiemann) 30 2.4 Tổng hợp phối tử bazơ Schiff phối tử 33 2.4.1 Tổng hợp dãy phối tử H2L1, H2L2, H2L3 33 2.4.2 Tổng hợp dãy phối tử HL4 39 2.5 Tổng hợp phức chất Pt(II) Pd(II) với phối tử bazơ Schiff 45 2.5.1 Tổng hợp phức chất với dãy phối tử H2L1, H2L2, H2L3 - 46 2.5.2 Tổng hợp phức chất với dãy phối tử HL4 56 CHƯƠNG KẾT QUẢ VÀ THẢO LUẬN 65 3.1 Nghiên cứu tổng hợp salicylaldehyde, phối tử phức chất 65 3.1.1 Nghiên cứu tổng hợp salicylaldehyde có nhóm R3, R5 65 d 3.1.2 Nghiên cứu tổng hợp phối tử phối tử - 65 3.1.3 Nghiên cứu tổng hợp phức chất với phối tử phối tử - 66 3.2 Nghiên cứu cấu trúc phối tử phức chất phương pháp phổ hồng ngoại 68 3.2.1 Phổ hồng ngoại dãy phối tử phức chất 68 3.2.2 Phổ hồng ngoại dãy phối tử phức chất 70 3.3 Nghiên cứu phức chất phương pháp phổ khối lượng - 72 3.4 Nghiên cứu cấu trúc phức chất phương pháp phổ NMR - 75 3.4.1 Nghiên cứu cấu trúc phức chất Pt(II), Pd(II) với dãy phối tử H2L1 75 3.4.2 Nghiên cứu cấu trúc phức chất Pt(II), Pd(II với dãy phối tử H2L2 - 82 3.4.3 Nghiên cứu cấu trúc phức chất Pt(II), Pd(II) với dãy phối tử H2L3 92 3.4.4 Nghiên cứu cấu trúc phức chất Pt(II), Pd(II) với dãy phối tử HL4 101 3.5 Nghiên cứu hoạt tính sinh học phối tử phức chất - 127 3.5.1 Hoạt tính kháng vi sinh vật phối tử phức chất 127 3.5.2 Khả ức chế phát triển tế bào ung thư phức chất - 127 3.6 Nghiên cứu mối tương quan cấu trúc - hoạt tính sinh học phức chất 130 KẾT LUẬN 139 NHỮNG ĐÓNG GÓP MỚI CỦA LUẬN ÁN - 140 TÀI LIỆU THAM KHẢO - 142 e DANH MỤC CÁC KÝ HIỆU, CHỮ VIẾT TẮT A549 Dòng ung thư biểu mơ tế bào phổi (human lung adenocarcinoma epithelial cells line) CC Sắc kí cột (Columm Chromatography) CDCl3 Chloroform deuteri hóa DNA Deoxyribo Nucleic Acid DCM Dichlorometan DMSO Dung môi dimethyl sulfoxide ESI-MS Phổ khối lượng phun mù điện tử (Electrospray Ionization Mass Spectrometry) EtOH Ethanol EtOAc Ethyl acetate H(%) Hiệu suất phản ứng (%) HCT-116 Dòng ung thư đại tràng (human colon carcinoma cell line) H2L Dãy phối tử dạng diimine N2O2, H nhóm OH HL Dãy phối tử dạng monoimine NO, H nhóm OH HL-60 Dòng ung thư tuyến tiền liệt (human leukemia cell line) HeLa Dòng tế bào ung thư biểu mơ (human epithelial carcinoma cell line) Hep-G2 Dòng tế bào ung thư gan (Human hepatocellular carcinoma cell line) HMBC Tương tác dị hạt nhân qua nhiều liên kết (Heteronuclear Multiple Bond Coherence) HSQC Tương tác dị hạt nhân qua liên kết (Heteronuclear Single Quantum Coherance) IR Phổ hồng ngoại (Infrared spectroscopy) IC50 Nồng độ chất thử ức chế 50% phát triển tế bào (Compound concentrations that produce 50% of cell growth inhibition) K562 Dòng tế bào ung thư máu cấp (Chronic myelogenous leukemic cell line) KB Lu Dòng tế bào ung thư biểu mơ (Human epidemoid carcinoma cell line) Dòng tế bào ung thư phổi (Lung carcinoma cell line) f L Phối tử (Ligand) M Kim loại chuyển tiếp hóa trị M(II) (Transition Metal) MCF-7 Dòng tế bào ung thư vú (Human breast adenocarcinoma cell line) MeOH Metanol MIC Giá trị nồng độ ức chế tối thiểu (Minimum Inhibitory Concentration values) MTT 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium N2O2 Phối tử bazơ Schiff dạng (diimine) NO Phối tử bazơ Schiff dạng (monoimine) P Phức chất (complex) PC3 Dòng tế bào ung thư tuyến tiền liệt (human prostate cancer cell line) Ph Nhóm phenyl rt Nhiệt độ phòng R Cấu hình (R) S Cấu hình (S) Salen Salicylaldehyde-ethylendiamine TLC Sắc kí lớp mỏng (Thin Layer Chromatography) TLTK Tài liệu tham khảo t-bu Nhóm tert-butyl br Broad d Mũi đơi (Doublet) dd Mũi đôi mũi đôi (Doublet of doublets) dm Nhiều mũi đôi (Doublet of multiplets) dt Doublet triplet m Nhiều mũi (Multiplet) ppm Phần triệu (Parts per million) q Mũi bốn (Quartet) s Mũi đơn (Singlet) t Mũi ba (Triplet) Phổ cộng hưởng từ hạt nhân proton proton 1H (Proton Nuclear H-NMR Magnetic Resonance spectroscopy) 13 C-NMR Phổ cộng hưởng từ hạt nhân carbon 13 (Carbon-13 Nuclear g Magnetic Resonance spectroscopy) J Hằng số tương tác spin-spin (Hz) Độ dịch chuyển hóa học (ppm) Ký hiệu 5ms Tên hóa học 5-methoxy-salicylaldehyde Công thức cấu tạo 3tbs 3-t-butyl-salicylaldehyde 5tbs 5-t-butyl-salicylaldehyde 3,5tbs 3,5-di-tert-butyl-salicylaldehyde 5Cls 5-chloro-salicylaldehyde 5Brs 5-bromo-salicylaldehyde 5Is 5-iodo-salicylaldehyde 5Fs 5-fluoro-salicylaldehyde H2spd N,N'-bis(salicylidene)-1,2phenylendiamine cis-H2scd N,N'-bis(salicylidene)cyclohexanediamine trans-H2scd N,N'-bis(salicylidene)- trans -1,2cyclohexanediamine cis-1,2- h H2sed N,N'-bis(salicylidene)-1,2ethylenediamine H25msed 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Nghiên cứu cấu trúc phức chất Pt(II), Pd(II) với dãy phối tử H2L3 92 3.4.4 Nghiên cứu cấu trúc phức chất Pt(II), Pd(II) với dãy phối tử HL4 101 3.5 Nghiên cứu hoạt tính sinh học phối tử phức. .. 65 d 3.1.2 Nghiên cứu tổng hợp phối tử phối tử - 65 3.1.3 Nghiên cứu tổng hợp phức chất với phối tử phối tử - 66 3.2 Nghiên cứu cấu trúc phối tử phức chất phương pháp phổ hồng... KHOA HỌC VÀ CÔNG NGHỆ VIỆT NAM HỌC VIỆN KHOA HỌC VÀ CÔNG NGHỆ …… ….***………… LÂM QUANG HẢI NGHIÊN CỨU TỔNG HỢP, XÁC ĐỊNH CẤU TRÚC VÀ THĂM DỊ HOẠT TÍNH SINH HỌC CỦA MỘT SỐ PHỨC CHẤT Pt(II), Pd(II) VỚI