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1 T DAC
2 (DAC) DAC 11 DAC8 DAC8 T Leukemia. 2008, 22, Clin. Cancer. Res. 2009, 15, DAC8 1)DAC8 2)
3 T T T-ALL 10 1 T-ALL 30~40% T CTCL 10 1 CTCL T ATLL 1 TLV ,000 TLV-1 16~41% 3~13
4 Click Chemistry Cu(I)-catalyzed Azide Alkyne Cycloaddition (CuAAC) Angew. Chem. Int. Ed. Engl. 2002, 41, CuAAC tris (benzyltriazolylmethyl)amine (TBTA) Cu(I) Cu(I) CuAAC rg. Lett.2004, 6,
5 Alkyne, Azide-unit ZBG Alkyne-unit (A):8 Drug Design Linker Zinc-Binding Group Cap (ZBG) vorinostat (Representative DAC Inhibitor) A1 A5 2 A2 A6 2 A3 A7 2 S S A4 A8 2 Cap DAC8 Selective Inhibitor Candidates ZBG Click Chemistry Cu(I) 3 n 3 Me B1: n=1 B4:n=4 B2: n=2 B5:n=5 B3: n=3 Cap B6 B7: m- B8: p- Azide-unit (B): B9: m- B10: p B11:1- B12:2- B13 B14 B15
6 CuAAC Triazole Library Alkyne-unit (A):8 Azide-unit (B):15 A1 A3 A4 S A2 3 n 3 Me B1:n=1 B4:n=4 B2:n=2 B5:n=5 B3:n=3 B6 B7: m- B8: p- 3 3 B9: m- B10: p- A5 2 A7 2 A8 2 S A6 2 B11: 1- B12: B13 B14 B15 TLC & LCMS Analysis CuS 4 5 2, 10 mol% Sodium Ascorbate, 50 mol% TBTA, 10 mol% DMS/ 2, rt, 1-3 days o Isolation & Purification DAC Fluorometric Assay
7 DAC Fluorophore C 3 DAC Fluorophore C 3 DEVELPER 360 nm 460 nm Detect!! DAC Activity Assay / Drug Discovery Kit, Fluorescent AK-500 (BIML TM ) DAC
8 PCI C10 C20 C30 C40 C50 C60 C70 C80 C90 C100 C110 C DAC8 (1) 0.3 μm Enzyme Activity (%)
9 PCI C10 C20 C30 C40 C50 C60 C70 C80 C90 C100 C110 C DACs (1) o Inhibition 0.3 μm Enzyme Activity (%)
10 C31, C32
11 DAC (2) Compound IC 50 (μm) a DACs class I class IIa class IIb (nuclear extract) DAC1 DAC2 DAC8 DAC4 DAC > vorinostat >100 >100 > > PCI C31 23 > > C32 a Values are means of at least three experiments.
12 DAC vorinostat C31 C32 PCI Control (2 M) (10 M) (50 M) (2 M) (10 M) (50 M) (2 M) (10 M) (50 M) (2 M) (10 M) (50 M) Ac SMC3 SMC3 Ac 3K9
13 Cell Line GI 50 (μm) a PCI C31 C32 Jurkat MLT4F T Cell > ut MT MT Rajii >100 >100 >100 B Cell Ramos >100 U266 > >100 K562 > >100 Solid Tumor ela ealthy PB PB- 97 >100 >100 PB- > >100 a Values are means of at least three experiments. C31, C32 T C31, C32 (PB-, ) T
14 C32 MacroModel 8.1, Glide 3.5 (DAC8, PDB: 1VKG) is142 Tyr306 Phe152 DAC8 Cap DAC8
15 Cap moiety C32 Cap C32 Lead ptimization Click Chemistry Cu(I) R C32 derivatives R 3 Azide-unit (B) A2 Azide Design & Synthesis R B16: 2-Me B17: 3-Me B18: 4-Me B19: 2-Me B20: 3-Me B21: 4-Me B22: 2-Cl B23: 3-Cl B24: 4-Cl 3 B25: 2-F B26: 3-F B27: 4-F B28: 2-CF 3 B29: 3-CF 3 B30: 4-CF 3 B31: 2-2 B32: 3-2 B33: 4-2 R B34: 1-aphtyl B35: 2-aphtyl B36: 3-Indolyl B37: 3-thienyl B38: 2-pyridinyl 3 B39: 4-methylthiazolyl B40: 4-morpholinyl B41: cyclopentyl B42: cyclohexyl B43: 1-adamantyl X 3 B44: X=SC 2 B45: X=CC 2 B46: X=CC (trans)
16 C32 C121 C122 C123 C124 C125 C126 C127 C128 C129 C130 C131 C132 C133 C134 C135 C136 C137 C138 C139 C140 C141 C142 C143 C144 C145 C146 C147 C148 C149 C150 C μm Enzyme Activity (%)
17 DACs (2) Enzyme Activity (%) C32 C121 C122 C123 C124 C125 C126 C127 C128 C129 C130 C131 C132 C133 C134 C135 C136 C137 C138 C139 C140 C141 C142 C143 C144 C145 C146 C147 C148 C149 C150 C μm
18 C32 C142 C149 C152, C153 A2, CuS 4 5 2, Sodium ascorbate, TBTA, Me/ 2 B44 S 3 mcpba (1.0 or 2.0 eq) C 2 Cl 2 X 3 B47: X=S,66% B48: X=S 2,97% A2 CuS Sodium ascorbate TBTA Me/ 2 X C149: X=S,94% C152: X=S,70% C153: X=S 2,54%
19 Compound DAC (2) IC 50 (μm) a DACs class I class IIa class IIb (nuclear extaract) DAC1 DAC2 DAC8 DAC4 DAC6 23 > > C32 44 >100 > > C > C149 > > C152 C153 > > a Values are means of at least three experiments.
20 DAC8 PCI GI 50 (μm) C32 GI 50 (μm) C149 GI 50 (μm) T-ALL Jurkat MLT4F T-cell lines CTCL > ut ealthy PB ATLL MT MT >100 >100
21 DAC8 DAC8 Click Chemistry
22 DAC8 T / cf) TSA (DAC / /
23 DAC
24
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