Erratum: Recognition of HIV TAR RNA by triazole linked neomycin dimers (Bioorganic and Medicinal Chemistry Letters (2011) 21 (4788-4792))

Full text of DOI:10.1016/j.bmcl.2011.12.058

Bioorganic & Medicinal Chemistry Letters 22 (2012) 1827–1829
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Bioorganic & Medicinal Chemistry Letters
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Corrigendum
Corrigendum to ‘‘Recognition of HIV TAR RNA by triazole linked neomycin
dimers’’ [Bioorg. Med. Chem. Lett. 21 (2011) 4788–4792]
⇑
Sunil Kumar, Dev P. Arya
Laboratory of Medicinal Chemistry, Department of Chemistry, Clemson University, Clemson, SC 29634, United States
An error occurred in Figure 4, Schemes 1 and 2, Table 1. The corrected scheme appears below.
14
12
10
8
O
O
O
O
6
O
4
2
0
Linker length
Figure 4. Bar graph representing the effect of linker length and structure of neomycin dimers on the binding affinity towards HIV-1 TAR RNA, determined using ethidium
bromide displacement experiments.
DOI of original article: 10.1016/j.bmcl.2011.06.058
Corresponding author.
E-mail address: dparya@clemson.edu (D.P. Arya).
⇑
0960-894X/$ - see front matter Ó 2011 Elsevier Ltd. All rights reserved.
doi:10.1016/j.bmcl.2011.12.058

1828
S. Kumar, D. P. Arya / Bioorg. Med. Chem. Lett. 22 (2012) 1827–1829
Hairpin Region
G G
U
G
A
C
NH2
C
G
O
G C
HO
A U
H2N
HO
U G C
NH2
H2N
O
O
Upper Stem
C
Bulge region
O
HO
U
OH
A U
G C
A U
C G
G C
G C
5' 3'
OH
NH2
OH
O
Lower Stem
O
OH
H2N
Neomycin
TAR RNA
HO
NH2
OH
O
O
HO
H2N
NH2
O
N
N
O
HO
HO
HO
N
O
H2N
O
NH2
X
NH2
H2N
O
H2N
O
OH
OH
NH2
N
O
O
H2N
N
OH
N
OH
NH2
OH
12 HCl
O
O
H2N
OH
X = represents varying linker length
or functionality
Neomycin dimer
Scheme 1. Structures of small molecule ligands (neomycin and neomycin dimer) and TAR RNA used in the study.

S. Kumar, D. P. Arya / Bioorg. Med. Chem. Lett. 22 (2012) 1827–1829
1829
NH2
O
HO
H2N
HO
NH2
H2N
O
O
O
HO
OH
OH
NH2
O
OH
O
H2N
OH
a-c
NHR
O
HO
HO
RHN
NHR
RHN
O
R = Boc
O
N3
NHR
O
OH
OH
OH
O
O
RHN
OH
d-e
HO
NH2
OH
O
O
HO
H2N
N
NH2
N
N
O
O
HO
HO
HO
O
H2N
O
NH2
X
NH2
H2N
O
H2N
O
OH
OH
NH2
N
O
O
H2N
N
OH
N
OH
NH2
OH
O
12 HCl
O
H2N
OH
Scheme 2. Reagents and conditions: (a) (Boc)2O, DMF, H2O, Et3N, 60 °C, 5 h, 60%; (b) TPS-Cl, pyridine, rt, 40 h, 50%; (c) NaN3, DMF/H2O (10/1), 12 h, 90 °C, 90%; (d) Toluene,
CuI, DIPEA, rt, 90 °C, 85-92%; (e) 4 M HCl/dioxane, rt, 5 min, 76-95%.
Table 1
Table of UV thermal denaturation of ligand/HIV TAR RNA complexes at rdd = 1 and
D
Tm.
Tm
Neomycin dimer
Structure of the linker
DTm
(-x-, from Schemes 1 and 2)
HIV 1 TAR RNA
DPA51
NA
68.9
79.1
NA
10.2
O
DPA52
DPA65
78.2
78.2
9.3
9.3
DPA53
DPA54
78.5
77.1
9.6
8.2
DPA55
76.4
7.6
DPA56
DPA58
74.9
74.3
6.1
5.4
O
O
4
O
O
6
DPA60
72.1
69.1
3.3
0.2
Neomycin
NA
Buffer conditions: 100 mM KCl, 10 mM SC, 0.5 mM EDTA, pH 6.8. [HIV TAR RNA] = 1
dimer] = 1 M. [Neomycin] = 1 M.
l
M/strand. [Neomycin
l
l