› suppdata › c5 › ob › c5ob00860c › c5ob00860c1.pdf · 2015-05-18 · locked nucleic acid...
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S1
Locked Nucleic Acid (LNA) induced effect on hybridization and fluorescence properties of
oligodeoxyribonucleotides modified with nucleobase-functionalized DNA monomers
Mamta Kaura and Patrick J. Hrdlicka*
Department of Chemistry, University of Idaho, 875 Perimeter Dr MS 2343, Moscow, ID 83844-2343, USA
* [email protected] (+1 208-885-0108)
ELECTRONIC SUPPLEMENTARY INFORMATION
Table of contents
MALDI-ToF MS of modified 9-mer ONs (Table S1) S2
Representative thermal denaturation curves (Figure S1) S3
Absorption spectra for pyrene-modified ONs and duplexes (Figures S2-S5) S4
Biophysical characterization of 13-mer Y/M-modified ONs S8
MALDI-ToF MS of modified 13-mer ONs (Table S2) S8
Thermal denaturation data for 13-mer Y- or M-modified ONs and duplexes
(Tables S3 and S4 S6) S9
Absorption spectra for 13-mer Y-modified ONs and duplexes (Figure S6) S10
Absorption maxima for 13-mer Y-modified ONs and duplexes (Table S5) S11
Absorption spectra for 13-mer M-modified ONs and duplexes (Figure S7) S12
Absorption maxima for 13-mer M-modified ONs and duplexes (Table S6) S13
Fluorescence emission spectra for 13-mer Y-modified ONs and duplexes (Figure S8) S14
Fluorescence emission spectra for 13-mer M-modified ONs and duplexes (Figure S9) S15
NMR spectra for nucleosides S16
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2015
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S2
Table S1. MALDI-ToF MS of modified 9-mer ONs.a
(M+H) (M+H)
ON Sequence CALC OBS ON Sequence CALC OBS
T2 5′-GTG aTa TGC 2809.5 2810.7 A5 5′-GCA tAt CAC 2739.5 2738.2
T3 5′-GTg ATA tGC 2809.5 2810.6 A6 5′-GCa TAT cAC 2752.5 2751.2
W1 5′-GTG AWA TGC 2762.5 2763.6 L4 5′-GCA TLT CAC 2706.5 2706.3
W2 5′-GTG aWa TGC 2818.5 2819.6 L5 5′-GCA tLt CAC 2775.0 2776.0
W3 5′-GTg AWA tGC 2818.5 2819.6 L6 5′-GCa TLT cAC 2761.5 2762.3
X1 5′-GTG AXA TGC 2791.5 2793.0 M4 5′-GCA TMT CAC 2907.7 2906.7
X2 5′-GTG aXa TGC 2847.5 2848.0 M5 5′-GCA tMt CAC 2977.0 2977.0
X3 5′-GTg AXA tGC 2847.5 2848.7 M6 5′-GCa TMT cAC 2964.7 2964.0
Y1 5′-GTG AYA TGC 2964.7 2962.1 N4 5′-GCA TNT CAC 2962.6 2963.3
Y2 5′-GTG aYa TGC 3020.7 3019.6 N5 5′-GCA tNt CAC 3033.6 3033.3
Y3 5′-GTg AYA tGC 3020.7 3020.0 N6 5′-GCa TNT cAC 3018.6 3021.0
Z1 5′-GTG AZA TGC 3019.6 3020.7
Z2 5′-GTG aZa TGC 3075.5 3076.6
Z3 5′-GTg AZA tGC 3075.5 3076.6
a A/C/G/T = adenin-9-yl/cytosin-1-yl/guanin-9-yl/thymin-1-yl DNA monomers. For structures of
monomers W/X/Y/Z and L/M/N, see Figure 1 in main manuscript. LNA modifications are
shown in lower case (“c” = 5-methylcytosine LNA monomer). Modified ONs were obtained in a
purity of at least 75%.
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Figure S1. Representative thermal denaturation curves of duplexes between
W2/Y2/Z2/L5/M5/N5 and complementary DNA or RNA targets. For experimental conditions,
see Table 1.
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S4
Figure S2. Absorption spectra of single-stranded Y1-Y3 and the corresponding duplexes with
complementary DNA/RNA (cDNA/cRNA) or centrally mismatched DNA targets (mismatched
nucleoside is specified) - for sequences of matched/mismatched targets, see footnote of Table 5.
Spectra were recorded in Tm buffer at T = 5 °C using each strand at 1 µM concentration.
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S5
Figure S3. Absorption spectra of single-stranded M4-M6 and the corresponding duplexes with
complementary DNA/RNA or centrally mismatched DNA targets (mismatched nucleoside is
specified) - for sequences of matched/mismatched targets, see footnote of Table 5. For
experimental conditions, see Figure S2.
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Figure S4. Absorption spectra of single-stranded Z1-Z3 and the corresponding duplexes with
complementary DNA/RNA or centrally mismatched DNA targets (mismatched nucleoside is
specified) - for sequences of matched/mismatched targets, see footnote of Table 5. For
experimental conditions, see Figure S2.
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Figure S5. Absorption spectra of single-stranded N4-N6 and the corresponding duplexes with
complementary DNA/RNA or centrally mismatched DNA targets (mismatched nucleoside is
specified) - for sequences of matched/mismatched targets, see footnote of Table 5. For
experimental conditions, see Figure S2.
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S8
Biophysical characterization of 13-mer Y/M-modified ONs. Systematic studies of 13-mer ONs,
in which the C5- or C8-ethynylpyrene functionalized monomers Y or M are directly flanked by
LNA nucleotides, were performed (Table S2). The observed trends mirror those for the 9-mer
ONs (see main manuscript), with the following exceptions: i) M11-M14 exhibit lower-than-
anticipated cDNA (Table S4), ii) Y10 displays minimal blue-shifts in pyrene absorption maxima
upon cDNA hybridization (Table S5), iii) M13 displays blue-shifts in pyrene absorption maxima
upon hybridization with matched/mismatched DNA targets; this may be due to a structured state
of the single-stranded probe (note the high absolute λmax
value for M13, Table S5), and iv)
hybridization of M11-M14 to cDNA targets does not result in increased emission.
Table S2. MALDI-ToF MS of modified 13-mer ONs.a
(M+H)
ON Sequence CALC OBS
Y7 5′-CG CAA aYa AAC GC 4185.0 4184.0
Y8 5′-CG CAA cYc AAC GC 4232.7 4233.0
Y9 5′-CG CAA gYg AAC GC 4180.7 4182.0
Y10 5′-CG CAA tYt AAC GC 4200.0 4202.0
M11 3′-GCGTT aMa TTGCG 4249.7 4250.6
M12 3′-GCGTT cMc TTGCG 4299.7 4300.0
M13 3′-GCGTT gMg TTGCG 4247.7 4248.0
M14 3′-GCGTT tMt TTGCG 4267.8 4268.5 a A/C/G/T = adenin-9-yl/cytosin-1-yl/guanin-9-yl/thymin-1-yl DNA monomers. LNA
modifications are shown in lower case (c = 5-methylcytosine LNA). For structures of monomers
Y and M, see Figure 1 in main manuscript.
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S9
Table S3. Thermal denaturation data for duplexes between Y-modified ONs and complementary
or singly mismatched DNA targets.
Tm/°C ∆Tm/°C
ON Sequence B = A C G T
Y7
5′-CG CAA aYa AAC GC 3′-GC GTT TBT TTG CG 45.0 0.0 +1.0
+1.0
Y8
5′-CG CAA cYc AAC GC 3′-GC GTT GBG TTG CG 57.0 -5.0 -2.0
-6.0
Y9
5′-CG CAA gYg AAC GC 3′-GC GTT CBC TTG CG 49.0 0.0 -8.0
-3.0
Y10
5′-CG CAA tYt AAC GC 3′-GC GTT ABA TTG CG 45.5 -1.0 -1.0
-3.0
aFor experimental conditions, see Table 1 in main manuscript. Tm’s of the duplexes between cDNA and the unmodified control ONs for Y7-Y10 are 48.5 °C, 55.5 °C, 55.0 °C and 48.5 °C, respectively. Tm = change in Tm’s relative to fully matched duplex (B = A).
Table S4. Thermal denaturation data for duplexes between M-modified ONs and complementary
or singly mismatched DNA targets.
Tm/°C ∆Tm/°C
ON Sequence B = T A C G
M11
5′-CGCAA TBT AACGC 3′-GCGTT aMa TTGCG 41.0 -0.5 +2.5
-0.5
M12
5′-CGCAA GBG AACGC 3′-GCGTT cMc TTGCG 54.0 -1.5 -2.5
-1.5
M13
5′-CGCAA CBC AACGC 3′-GCGTT gMg TTGCG 47.0 +1.5 +2.5
-3.5
M14
5′-CGCAA ABA AACGC 3′-GCGTT tMt TTGCG 42.0 -1.5 -0.5
+1.5
aFor experimental conditions, see Table 1 in main manuscript. Tm’s of the duplexes between cDNA and the unmodified control ONs for M11-M14 are 48.5 °C, 55.0 °C, 55.5 °C and 48.5 °C, respectively. Tm = change in Tm’s relative to fully matched duplex (B = T).
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S10
Figure S6. Absorption spectra of 13-mer Y-modified ONs and the corresponding duplexes with
complementary or centrally mismatched DNA targets (nucleoside opposite of monomer Y is
specified) – for sequences see Table S3. Spectra were recorded in Tm buffer at T = 5 °C using
each strand at 1 µM concentration.
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S11
Table S5. Absorption maxima of 13-mer Y-modified ONs in the presence or absence of
complementary or singly mismatched DNA targets (nucleoside opposite of monomer Y is
specified).
λmax
/nm (∆λ
max)
ON Sequence SSP B = A B = C B = G B = T Y7 5′-CG CAA aYa AAC GC
3′-GC GTT TBT TTG CG 399 -1 +4 +1 +5 Y8 5′-CG CAA cYc AAC GC
3′-GC GTT GBG TTG CG 402 -4 +2 +2 +2 Y9 5′-CG CAA gYg AAC GC
3′-GC GTT CBC TTG CG 403 -6 +2 -1 +1 Y10 5′-CG CAA tYt AAC GC
3′-GC GTT ABA TTG CG 400 +0 +4 ±0 ±0 a Recorded in Tm buffer at T = 5 °C using 1.0 µM of each strand. SSP = single-stranded probe.
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S12
Figure S7. Absorption spectra of 13-mer M-modified ONs and the corresponding duplexes with
complementary or centrally mismatched DNA targets (nucleoside opposite of monomer M is
specified) – for sequences see Table S4. Spectra were recorded in Tm buffer at T = 5 °C using
each strand at 1 µM concentration.
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S13
Table S6. Absorption maxima of 13-mer M-modified ONs in the absence (SSP) or presence of
complementary or singly mismatched DNA targets (nucleoside opposite of monomer M is
specified).a
λmax
/nm (∆λ
max)
ON Sequence SSP B = T B = C B = G B = A
M11 3′-GCGTT aMa TTGCG 5′-CGCAA TBT AACGC
415 +2 +3 +2 +2
M12 3′-GCGTT cMc TTGCG 5′-CGCAA GBG AACGC
418 +4 +5 +5 +5
M13 3′-GCGTT gMg TTGCG 5′-CGCAA CBC AACGC
422 -4 -3 -5 -5
M14 3′-GCGTT tMt TTGCG 5′-CGCAA ABA AACGC
415 +4 +3 +3 +5
[a] Recorded in Tm buffer at T = 5 °C using 1.0 µM of each strand. SSP = single-stranded probe.
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S14
Figure S8. Steady-state fluorescence emission spectra of 13-mer Y-modified ONs in the
presence or absence of complementary or centrally mismatched DNA targets (mismatched
nucleoside opposite of monomer Y is specified) – for sequences see Table S3. Spectra were
recorded in Tm buffer at T = 5 °C using each strand at 1 µM concentration and ex = 380 nm.
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S15
Figure S9. Steady-state fluorescence emission spectra of 13-mer M-modified ONs in the
presence or absence of complementary or centrally mismatched DNA targets (mismatched
nucleoside opposite of monomer M is specified) – for sequences see Table S4. Spectra were
recorded in Tm buffer at T = 5 °C using each strand at 1 µM concentration, ex = 385 nm.
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2
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2
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2
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2
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2
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S24
5L
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S25
5L
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S26
5L
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S27
5L
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S28
5L
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S29
5L
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S30
5L
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S31
5L
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S32
5M
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S33
5M
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S34
5M
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S35
5M
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S36
5M
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S37
5M
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