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Title Page

Contents

General Introduction 8

Part 1. Phenanthromethyl pyroglutamates: a new class of potent M. tuberculosis-specific drugs 10

ABSTRACT 11

Materials and Methods 13

Results and Discussion 29

Conclusion 57

References 58

국문초록 62

Part 2. In vitro activity of alpha-viniferin isolated from the roots of Carex humilis against Mycobacterium tuberculosis 64

ABSTRACT 65

Materials and Methods 67

Results and Discussion 73

Conclusion 86

References 87

국문초록 90

List of Tables

Part 1 30

Table 1. Structures of DPG analogues, their in vitro anti-tubercular activity against M.... 30

Table 2. In vitro anti-tuberculosis activity of phenanthromethyl pyroglutamates and... 37

Table 3. Effectiveness of phenanthromethyl pyroglutamates in combination with first- line... 39

Table 4. Determination of the MIC values of phenanthromethyl pyroglutamates and 5... 48

Table 5. Number of M. tuberculosis genes differentially expressed following 1× and... 49

Table 6. Number of genes (fold change cutoffs of 〉 2) regulated in M. tuberculosis... 50

Part 2 76

Table 1. Anti-tuberculosis activity of α-viniferin and control drugs against M.... 76

Table 2. Effectiveness of α-viniferin in combination with first-line drugs for anti-... 79

Table 3.Determination of the MIC of α-viniferin and five control drugs against 23... 84

List of Figures

Part 1 15

Figure 1. General scheme for the synthesis of DPG analogues. 15

Figure 2. Circular dichroism spectra of PP5S, PP14S, PP13S, and PP13R. 22

Figure 3. (a) Structure of 6,7-dimethoxy-3-alkoxy-9-phenanthrenecarboxylic acid and (b)... 29

Figure 4. Comparative efficacy of phenanthromethyl pyroglutamates in vitro and ex vivo 33

Figure 5. Anti-tubercular activity of phenanthromethyl pyroglutamates against M.... 35

Figure 6. Intracellular killing activity and the modulation of M. tuberculosis-induced... 36

Figure 7. Mean body weight of (a) male and (b) female rats. A single dose of 500, 1000,... 42

Figure 8. Efficacy of PP5S in a mouse model of chronic pulmonary tuberculosis. 43

Figure 9. Anti-tubercular activity of phenanthromethyl pyroglutamates and control drugs... 45

Figure 10. Mode of action of phenanthromethyl pyroglutamates. 46

Figure 11. Changes in protein expression in PP5S treated M. tuberculosis. 54

Figure 12. Purification and microarray analysis of Rv0560c protein. 56

Part 2 74

Figure 1. Chemical structure of α -viniferin isolated from the roots of C. humilis. 74

Figure 2. The UV-vis absorption and HPLC chromatogram of α -viniferin isolated from the... 75

Figure 3. Anti-tuberculosis activity of α-viniferin against M. tuberculosis H37Rv (A, C) and... 78

Figure 4. Cytotoxicity of α-viniferin against A549, Raw 264.7, and L929 cells as evaluated... 80

Figure 5. Intracellular killing activity of α-viniferin against M. tuberculosis H37Rv and XDR... 82

Figure 6. Antimicrobial activity of α -viniferin against methicillin-susceptible Staphylococcus... 85

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