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title page

ABSTRACT

Contents

CHAPTER I. Introduction 14

1.1. Platinum-based antitumor complexes 14

1.2. Structure and Properties of Cyclodextrins 30

1.3. Rotaxanes and Pseudorotaxanes 33

1.4. Polyazomethines 35

1.5. Objectives of Thesis 40

1.6. References 41

CHAPTER II. Nanoencapsulation as a tool: water-solubility of the anticancer drug trans-[PtCl₂(pyridine)]₂ by supramolecular complexation with β-cyclodextrin 46

2.1. Introduction 47

2.2. Experimental Section 48

2.3. Results and Discussion 52

2.4. Conclusion 66

2.5. References 67

CHAPTER III. Water-soluble tarns-platinum(II) derivative by supramolecular complexation with poly(β-cyclodextrin-triazine) 69

3.1. Introduction 70

3.2. Experimental Section 71

3.3. Results and discussions 75

3.4. Conclusions 86

3.5. References 87

CHAPTER IV. Synthesis of a novel water-soluble high molar mass polyazomethine rotaxane 88

4.1. Introduction 89

4.2. Experimental Section 91

4.3. Results and Discussions 99

4.4. Conclusion 106

4.5. References 107

SUMMARY 108

Acknowledgements 110

List of Tables

Table 1.1. Physical properties and molecular dimension of cyclodextrins 32

Table 2.1. Inhibitory concentrations (IC50) values calculated for cisplatin, DDP and DDP- CD inclusion complex (μM).(이미지참조) 64

Table 2.2. Different platinum derivatives and their suitable solvents 65

Table 3.2. Inhibitory concentrations (IC50) values calculated for cisplatin, DDP and DDP-CDTz inclusion complex (μM).(이미지참조) 83

Table 4.1. Condensation of Inclusion Complexes Yielding Poly(azomethine)s with Pseudorotaxane and Rotaxane Architecture. 105

List of Figures

Figure 1.1. Chemical structure of carboplatin, cisplatin and oxaliplatin. 15

Figure 1.2. Structure of trans-[PtCl₂(amine)(isopropylamine)], where amine = n, n- dimethylamine, propylamine, and butylamine. 16

Figure 1.3. Structure of piperazine and piperidine complexes. 17

Figure 1.4. Structure of trans-[PtCl₂(isopropylamine)(3-(hydroxymethyl-pyridine)] and trans-[PtCl₂(isopropylamine)(4-(hydroxymethyl)-pyridine)]. 18

Figure 1.5. Structure of 4-methyl and 4-ethyl substituted (trans-cyclohexane-1,2-diamine)oxalatoplatinum(II) complexes, rac-l(eq/ax) and rac-2(eq/ax). 18

Figure 1.6. Schematic representation of trans-platinum complexes with phosphines and amines as carrier ligands. 19

Figure 1.7. Structure of trans-[PtCl₂(OH)₂(dimethylamine)(isopropylamine)] and trans-[PtCl₂(OH)₂(dimethylamine)(isopropylamine)]. 20

Figure 1.8. Structure of cationic trans-Pt(II)Cl₂ complexes containing as inert groups NH₃ and piperazine, 4-picoline and piperazine, n-butylamine and piperazine, and NH₃ and 4-piperidino-piperidine. 21

Figure 1.9. Structure of piperazine complexes active against cisplatin resistant ovarian cancer cell lines. 22

Figure 1.10. Structure of trans-[PtCl₂(amine)(dimethylamine)] and trans-[PtCl₂(amine)(dimethylamine)] complexes. 22

Figure 1.11. Structure of trans-dichlorobis(diethyl pyridine-4-ylmethylphosphonate-N)platinum(II). 23

Figure 1.12. Structure of trans-[Pt(O₂CR)₂(L) (L')], (L = NH₃, L' = pyridine, quinoline, isoquinoline; L = L' = pyridine; R = H, CH₃, CH₂0H. 24

Figure 1.13. Structure of the three isomers of trans-[PtCl₂(NH₃)(metyl-piperidine)], 2-methylpiperidine, 3-methylpiperidine and 4-methylpiperidine. 24

Figure 1.14. Structure of trans-Pt(NH₃)LCl₂ containing pyridine, where L = 2-hydroxypyridine, 3-hydroxypyridine, imidazole, and imidazo(1,2-α)pyridine. 25

Figure 1.15. Structure of trans-bis(3-hydroxypyridine)dichloroplatinum(II), trans-bis(4- hydroxypyridine) dichloroplatinum(II), trans-tris(3-hydroxypyridine) dichloroplatinum(II) and trans-bis(imidazo[1,2-α]pyridine) dichloroplatinum(II). 26

Figure 1.16. Structure of trans-[Pt(OAc)₂(isopropylamine)(N-methylimidazole)] and trans-[Pt(OAc)₂(isopropylamine)(N-methylpyrazole)]. 27

Figure 1.17. Structure of trans,trans,trans-[Pt(N₃)₂(OH)₂(NH₃)₂] and cis,trans,cis- [Pt(N₃)₂(OH)₂(NH₃)₂]. 27

Figure 1.18. Trans-[PtCl₂(Am)(pip-pip)]HCl complexes. 28

Figure 1.19. Structure of cis-[PtCl₂py(5-SO₃H-isoquinoline)], trans-PtPy and cis-PtPy. 29

Figure 1.20. a) Structure of β-cyclodextrin, b) and 3D view of β-cyclodextrin. 30

Figure 1.21. Inner structure of cyclodextrin. 31

Figure 1.22. Schematic representation of pseudo-polyrotaxanes and polyrotaxanes. 34

Figure 1.23. Structure of fullerene-terminated polyazomethine rotaxane. 35

Figure 1.24. Schematic representation of the formation of polypseudorotaxane and polyazomethine backbone. 36

Figure 1.25. Structure of polyazomethine with p-aminophenyltriphenylmethane blocking ends. 37

Figure 1.26. Structure of cis- and trans-1,2-bis(4-aminophenyl)-1,2-diphenyletylene. 38

Figure 1.27. Structure of polyazomethine with methoxy and 2-ethylhexyloxy side chains. 39

Figure 2.1. X-ray diffraction pattern of a) DDP, b) CD, and c) CD-DDP inclusion complex. 53

Figure 2.2. FT-IR spectra of a) CD-DDP inclusion complex, b) CD, and c) DDP. 55

Figure 2.3. Thermo gravimetric curves of a) CD, b) CD-DDP inclusion complex, and c) DDP. 56

Figure 2.4. ¹H NMR spectra of a) DDP, b) CD-DDP inclusion complex, and c) CD. 58

Figure 2.5. SEM images of a) CD, b) potassium tetrachloroplatinate(II), c) DDP, and d) CD-DDP inclusion complex. 60

Figure 2.6. Space-filling energy-minimized (MM2) molecular models showing different views of DDP encapsulated in the CD cavity. 61

Figure 2.7. 3D plot showing the IC50 values of CPT, DDP and CD-DDP inclusion complex in CT and B16F10 cell lines.(이미지참조) 63

Figure 2.8. 3D plot showing the IC50 values of CPT, DDP and CD-DDP inclusion complex in CT 26 and B16F10 cell lines (calculations referred to Pt metal).(이미지참조) 64

Figure 3.1. Chemical structure of poly(β-cyelodextrin-triazine) and platinum complex trans-[PtCl₂(pyridine)₂]. 75

Figure 3.2. Far-IR spectrum of trans-[PtCl₂(pyridine)₂] 76

Figure 3.3. FT-IR spectra of a) trans-[PtCl₂(pyridine)₂]-poly(β-cyclodextrin-triazine) inclusion complex, b) poly(β-cyclodextrin-triazine), and c) trans- [PtCl₂(pyridine)₂]. 78

Figure 3.4. Thermo gravimetric curves of trans-[PtCl₂(pyridine)₂] complex with and without poly(β-cyclodextrin-triazine) encapsulation. a) poly(β- cyclodextrin-triazine)(PolyCDTz), b) trans-[PtCl₂(pyridine)₂] (DDP), c)... 79

Figure 3.5. ¹H-NMR spectra of trans-[PtCl₂(pyridine)₂] complex with and without poly(β-cyclodextrin-triazine) encapsulation. a) poly(β-cyclodextrin-triazine), b) trans-[PtCl₂(pyridine)₂]-poly(β-cyclodextrin-triazine)... 80

Figure 3.6. SEM images of a) trans-[PtCl₂(pyridine)₂], b) poly(β-cyclodextrin-triazine), c) trans-[PtCl₂(pyridine)₂]-poly(β-cyclodextrin-triazine) inclusion complex. 82

Figure 3.7. Measurement of relative cell viability vs. concentration. 84

Figure 3.8. 3D plot showing the IC50 values of cisplatin, trans-[PtCl₂(pyridine)₂] and trans-[ptCl₂(pyridine)₂]-poly(β-cyclodextrin-triazine) inclusion complex in CT26 and B16F10 cell lines....(이미지참조) 85

Figure 4.1. ¹H-NMR spectrum of the precursor inclusion complex between cyclodextrin and terephthalaldehyde (CD-TD). 92

Figure 4.2. TGA of the precursor inclusion complex between cyclodextrin and terephthalaldehyde (CD-TD). 93

Figure 4.3. FT-IR spectra of the precursor inclusion complex between cyclodextrin terephthalaldehyde and (CD-TD). 94

Figure 4.4. ¹H-NR spectrum of the precursor inclusion complex between cyclodextrin and polyoxipropylenediamine (CD-POPD). 95

Figure 4.5. FT-IR spectra of the precursor inclusion complex between cyclodextrin and polyoxyropylenediamine (CD-POPD). 96

Figure 4.6. TGA of the precursor inclusion complex between cyclodextrin and polyoxipropylenediamne (CD-POPD). 97

Figure 4.7. Titration curve of POPD with CD in aqueous solution at 25℃ 99

Figure 4.8. NR spectrum of the products; a) ¹H-NMR of polymer 1 and pseudorotaxane 4 in DMSO-d6 b) ¹³C-NMR of polyrotaxane 5 in DMSO-d6.(이미지참조) 101

Figure 4.9. FTIR spectra of pseudorotaxane 4 and polyrotaxane 5. 102

Figure 4.10. TGA of polymer 1, pseudorotaxane 4 and polyrotxane 5, and CD. 103

Figure 4.11. Molecular model (MM2 energy-minimized) of a short segment of the macromolecule 5. 105

List of Schemes

Scheme 1.1. Synthesis of rotaxane and pseudorotaxane. 33

Scheme 2.1. Synthesis of the inclusion of trans-dichloro(dipyridine)platinum(II) in the cavity of β-cyclodextrin. 50

Scheme 2.2. Schematic illustration of the inclusion of trans-dichloro(dipyridine) platinum(II) in the cavity of β-cyclodextrin. 54

Scheme 3.1. Synthesis of the trans-dichloro(dipyridine)platinum(II) (DDP) complex. 73

Scheme 4.1. Synthesis of the poly(azomethine) rotaxane by condensation of poly(oxypropylene)diamne and terephthaldehyde as monomers which are inclusion complexed with CD and giving Fullerene as the end-capping agent. 90

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