edward b. skibo, akmal jamil, douglas hansen, and brittany ... · edward b. skibo, akmal jamil,...
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1
Supplementry Information for
Triple Molecular Target Approach to Selective Melanoma Cytotoxicity
Edward B. Skibo, Akmal Jamil, Douglas Hansen, and Brittany Austin
Table of Contents:Page S2, H-NMR for Compound LD-1Page S3, MALDI for Compound LD-1Page S4, H-NMR for Compound DL-1Page S5, MALDI for Compound DL-1Page S6, H-NMR for Compound DD-1Page S7, MALDI for Compound DD-1Page S8, H-NMR for Compound 6aPage S9, COSY for Compound 6aPage S10, MS for Compound 6aPage S11, H-NMR for Compound 6bPage S12, COSY for Compound 6bPage S13, MS for Compound 6bPage S14, H-NMR for Compound 6cPage S15, COSY for Compound 6cPage S16, MS for Compound 6cPage S17, H-NMR for Compound 6dPage S18, COSY for Compound 6dPage S19, MS for Compound 6dPage S20, H-NMR for Compound 6ePage S21, COSY for Compound 6ePage S22, MS for Compound 6ePage S23, H-NMR for Compound 7aPage S24, COSY for Compound 7aPage S25, MS for Compound 7aPage S26, H-NMR for Compound 7bPage S27, COSY for Compound 7bPage S28, MS for Compound 7bPage S29, H-NMR for Compound 7cPage S30, COSY for Compound 7c
Page S31, MS for Compound 7cPage S32, H-NMR for Compound 7dPage S33, COSY for Compound 7dPage S34, MS for Compound 7dPage S35, H-NMR for Compound 7ePage S36, COSY for Compound 7ePage S37, MS for Compound 7ePage S38, H-NMR for Compound 2aPage S39, MALDI for Compound 2aPage S40, H-NMR for Compound 2bPage S41, MALDI for Compound 2bPage S42, H-NMR for Compound 2cPage S43, MALDI for Compound 2cPage S44, H-NMR for Compound 2dPage S45, MALDI for Compound 2dPage S46, H-NMR for Compound 2ePage S47, MALDI for Compound 2ePage S48 Mean graph for LL-1Page S49 Mean graph for DL-1Page S50 Mean graph for LD-1Page S51 Mean graph for DD-1Page S52 Mean graph for 2aPage S53 Mean graph for 2bPage S54 Mean graph for 2cPage S55 Mean graph for 2dPage S56 Mean graph for 2ePage S57 Mean graph for 2f
2
O
O
N
NN
N
H
O
N
H
O
NH2
LD1
3
O
O
N
NN
N
H
O
N
H
O
NH2
LD1
M+H+
M+Na+
4
O
O
N
NN
(S) N(R)
H
O
(E)N
H
(S)
O
NH2
DL1
5
O
O
N
NN
(S) N(R)
H
O
(E)N
H
(S)
O
NH2
DL1
M+H+
M+Na+
6
O
O
N
NN
(S) N(R)
H
O
(E)N
H
(R)
O
NH2
DD1
7
O
O
N
NN
(S) N(R)
H
O
(E)N
H
(R)
O
NH2
DD1
M+H+
M+Na+
8
6a
N
NN
H
NH
O
O
O
O
Br
N
O O
9
6a
N
NN
H
NH
O
O
O
O
Br
N
O O
10
6a
N
NN
H
NH
O
O
O
O
Br
N
O O
11
6b
N
N
N
H
NH
O
O
O
F
Br
N
O O
12
6b
N
N
N
H
NH
O
O
O
F
Br
N
O O
13
6b
N
N
N
H
NH
O
O
O
F
Br
N
O O
14
N
N
NBr
N
OO
H
NH
O
O
O
F
F
F
6c
15
N
N
NBr
N
OO
H
NH
O
O
O
F
F
F
6c
C3-H
Amide NH
Urethane NH
Phenylalaninemethine
Phenylalaninemethylene
C1- methyleneC2- methylene
16
N
N
NBr
N
OO
H
NH
O
O
O
F
F
F
6c
17
6d
N
N
N
H
NH
O
O
O
Br
N
O O
18
6d
N
N
N
H
NH
O
O
O
Br
N
O O
19
6d
N
N
N
H
NH
O
O
O
Br
N
O O
20
6e6e
N
N
NBr
N
OO
H
NH
O
O
O
F
21
6e
N
N
NBr
N
OO
H
NH
O
O
O
F
22
6e
N
N
NBr
N
OO
H
NH
O
O
O
F
23
7a
N
N
N
H
NH
O
O
O
O
O
O
24
7a
Phenylalanine Aromatic
Phenylalanine Aromatic
Urethane NH
Amide NH
6-H
3-HPhenylalanine Methine
Phenylalanine Methylene
C-2 methylene
N
N
N
H
NH
O
O
O
O
O
O1
2
3
45
6
7
8
25
7a
N
N
N
H
NH
O
O
O
O
O
O
26
7b
N
N
N
H
NH
O
O
O
F
O
O
27
7b
N
N
N
H
NH
O
O
O
F
O
O
28
7b
N
N
N
H
NH
O
O
O
F
O
O
29
7c
N
N
N
H
NH
O
O
O
F
F
F
O
O
30
7c
N
N
N
H
NH
O
O
O
F
F
F
O
O
31
7c
N
N
N
H
NH
O
O
O
F
F
F
O
O
32
7d
N
N
N
H
NH
O
O
O
O
O
33
7d
N
N
N
H
NH
O
O
O
O
O
34
7d
N
N
N
H
NH
O
O
O
O
O
35
7e
N
NN
H
NH
O
O
O
FO
O
36
7e
N
NN
H
NH
O
O
O
FO
O
37
7e
N
NN
H
NH
O
O
O
FO
O
38
N
NN
H
NH2
O
O
O
N
OCH3
2a
39
N
NN
H
NH2
O
O
O
N
OCH3
2a
40
2b
N
NN
H
NH2
O
O
O
N
F
41
M+H+
M+Na+
2b
N
NN
H
NH2
O
O
O
N
F
42
N
NN
H
NH2
O
O
O
N
CF3
2c
43
N
NN
H
NH2
O
O
O
N
CF3
2c
44
N
NN
H
NH2
O
O
O
N
CH3
2d
45
N
NN
H
NH2
O
O
O
N
CH3
2d
M+H+
M+Na+
46
N
NN
H
NH2
O
FO
O
N
2e
47
N
NN
H
NH2
O
FO
O
N
2e
M+H+
M+Na+
48
Prostate
Ovarian
NSC LungLeukemia
Colon
Renal
Breast
CNS
Melanoma
Mean Graph for LL-1
49
Prostate
Ovarian
NSC LungLeukemia
Colon
Renal
Breast
CNSMelanoma
Mean Graph for DL-1
50
Prostate
Ovarian
NSC LungLeukemia
Colon
Renal
Breast
CNSMelanoma
Mean Graph for LD-1
51
Prostate
Ovarian
NSC LungLeukemia
Colon
Renal
Breast
CNSMelanoma
Mean Graph for DD-1
52
Prostate
Ovarian
NSC LungLeukemia
Colon
Renal
Breast
CNSMelanoma
Mean Graph for 2aOCH3
O
O
N
NN
N
H
O
NH2
53
Prostate
Ovarian
NSC LungLeukemia
Colon
Renal
Breast
CNSMelanoma
Mean Graph for 2bO
O
N
NN
N
H
O
NH2
F
54
Prostate
Ovarian
NSC LungLeukemia
Colon
Renal
Breast
CNSMelanoma
Mean Graph for 2cCF3
O
O
N
NN
N
H
O
NH2
55
Prostate
Ovarian
NSC LungLeukemia
Colon
Renal
Breast
CNSMelanoma
Mean Graph for 2dO
O
N
NN
N
H
O
NH2
56
AJ-84-147, 742692
O
O
N
NN
N
H
O
NH2
F
57
Prostate
Ovarian
NSC LungLeukemia
Colon
Renal
Breast
CNSMelanoma
Mean Graph for 2eO
O
N
NN
N
H
O
NH2
F