supplementary information cytotoxicity dna/protein binding ...sellamuthu kathiresana, subramanian...
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Supplementary Information
Mixed-ligand copper(II)-phenolate complexes: structure and studies on
DNA/protein binding profile, DNA cleavage, molecular docking and
cytotoxicity
Sellamuthu Kathiresana, Subramanian Mugeshb, Maruthamuthu Muruganb, Feroze Ahamedb
and Jamespandi Annaraja*
aDepartment of Materials Science, School of Chemistry, Madurai Kamaraj University,
Madurai-625021, Tamil Nadu, India. E-mail address: [email protected]
bDepartment of Microbial Technology, School of Biological Sciences, Madurai Kamaraj
University, Madurai-625 021, Tamil Nadu, India
Table of Contents:
1. 1H and 13C NMR spectra of the ligand ……………………………….. S1-S2
2. UV-vis spectrum of L and complexes ………………………………… S3
3. ESI-MS spectra of ligand and complexes …………………................... S4-S8
4. CV spectrum of complexes 3 and 4 in CH3CN solvents ………………. S9
5. DNA studies of CV and DPV in complexes 1, 2 and 4 ………………... S10-S12
6. Docking protocol validated with removal of ClO4 from complex 4 …… S13
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2015
Fig. S1 1H-NMR spectra of 4-chloro-2-((2-phenylthio)phenylimino)methyl)phenol (L).
OHN
S
Cl
Fig. S2 13C-NMR spectra of 4-chloro-2-((2-(phenylthio)phenylimino)methyl)phenol (L).
OHN
S
Cl
Fig. S3 UV-vis spectrum of L and complexes (1-4).
Fig. S4 ESI-MS spectra of Schiff base ligand (L).
160BL #21 RT: 0.27 AV: 1 NL: 9.93E3T: ITMS + c ESI Full ms [50.00-1000.00]
100 200 300 400 500 600 700 800 900 1000m/z
0
10
20
30
40
50
60
70
80
90
100
Rel
ativ
e A
bund
ance
340.09
197.22382.10
241.11 297.09 560.22436.15
685.39171.27 582.22 803.60102.28 452.12 955.91864.23
OHN
S
Cl
Fig. S5 ESI-MS spectra of Cu(II) complex 1.
Fig. S6 ESI-MS spectra of Cu(II) complex 2.
16OBMC1_150123155420 #226 RT: 0.64 AV: 1 NL: 7.98E3T: ITMS + c ESI Full ms [150.00-1000.00]
200 300 400 500 600 700 800 900 1000m/z
0
10
20
30
40
50
60
70
80
90
100
Rel
ativ
e A
bund
ance
400.94
803.81583.08740.81 840.96
957.48536.15418.75201.85 340.11 613.95 722.06274.97 924.13
ON
S
Cl
CuOClO3
160BCL1_150110183637 #171 RT: 0.49 AV: 1 NL: 1.30E4T: ITMS + c ESI Full ms [150.00-1000.00]
200 300 400 500 600 700 800 900 1000m/z
0
10
20
30
40
50
60
70
80
90
100
Rel
ativ
e A
bund
ance
581.03
402.99
301.96243.02
420.35341.19 482.07181.05 597.00 866.62684.73 721.20 953.61
ON
S
Cl
Cu
N
N
Fig. S7 ESI-MS spectra of Cu(II) complex 3.
Fig. S8 ESI-MS spectra of Cu(II) complex 4.
16OBCL2_150110183637 #190 RT: 0.54 AV: 1 NL: 5.22E3T: ITMS + c ESI Full ms [150.00-1000.00]
200 300 400 500 600 700 800 900 1000m/z
0
10
20
30
40
50
60
70
80
90
100R
elat
ive
Abu
ndan
ce558.88
400.99
277.91390.90220.02 537.29 769.76 850.02708.42 895.85660.59592.72477.37330.94 955.03
ON
S
Cl
N
N
Cu
ON
S
Cl
N
N
Cu
160BCL3_150123155420 #124 RT: 0.35 AV: 1 NL: 7.91E3T: ITMS + c ESI Full ms [150.00-1000.00]
200 300 400 500 600 700 800 900 1000m/z
0
10
20
30
40
50
60
70
80
90
100
Rel
ativ
e A
bund
ance
584.96
305.96400.89
246.98
340.01685.36 783.71 818.89605.06 894.56418.20202.19 518.66 952.99
Fig. S9 Cyclic voltammograms of the complexes 3 (a) and 4 (b) in CH3CN (0.1 TBAP) on a
GC working electrode. Scan rate 100 mV s-1
Fig. S10 CV and DPV of 1 in the absence and presence of HS-DNA at scan rate of
100 mV s-1.
Fig. S11 CV and DPV of 2 in the absence and presence of HS-DNA at scan rate of
100 mV s-1.
Fig. S12 CV and DPV of 4 in the absence and presence of HS-DNA at scan rate of
100 mV s-1.
Fig. S13 Docked image of 423D bound ligand with remove of ClO4 coordinate.
Table S1:
The calculated E-total value of docking protocol was validated with the removal of ClO4
from complex 4 with DNA (423D)
Complex E-Total Value
(kcal mol-1)
Inhibitory constant
(µM)
Binding region
423D bound ligand -4.31 692.14 AT-GC