Structural Characterization, Antimicrobial Activity and BSA/DNA Binding Affinity of New Silver(I) Complexes with Thianthrene and 1,8-Naphthyridine
Abstract
:1. Introduction
2. Results
2.1. Synthesis and Characterization of Silver(I) Complexes Ag1–3
2.1.1. Solid-State Characterization
2.1.2. Solution Behavior
2.2. Biological Evaluation of the Silver(I) Complexes Ag1–3
2.2.1. Antimicrobial and Antiproliferative Effect of Silver(I) Complexes Ag1–3
2.2.2. C. elegans Toxicity
2.3. BSA Binding Study
2.4. Lipophilicity Assay
2.5. DNA Interaction
3. Materials and Methods
3.1. Materials
3.2. Measurements
3.3. Synthesis of Silver(I) Complexes Ag1–3
3.4. Air/Light Stability
3.5. Crystallographic Data Collection and Refinement of the Structures
3.6. Antimicrobial Studies
3.7. Toxicity Assessment
3.7.1. MTT Assay
3.7.2. C. elegans Survival Assay
3.8. BSA Binding Study
3.9. Lipophilicity Assay
3.10. DNA Interaction
3.10.1. Fluorescence Emission Spectroscopy
3.10.2. Gel Electrophoresis Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Distance (Å) | Ag1 | Distance (Å) | Ag2 | Ag3 | |
---|---|---|---|---|---|
Ag1–O1 | 2.360(2) | Ag1–O1 | 2.555(2) | 2.449(4) | |
Ag1–O2 | 2.328(2) | Ag1···O2 ii | 2.645(2) | – | |
Ag1–S1 | 2.6198(7) | Ag1–N1 | 2.200(2) | 2.186(3) | |
Ag1–S2 i | 2.6747(8) | Ag1–N2 i | 2.218(2) | 2.184(3) | |
Ag1···Ag1 i | 2.7871(5) | 2.7235(6) | |||
Angle (°) | Angle (°) | ||||
O1–Ag1–O2 | 108.07(7) | O1–Ag1–N1 | 112.75(8) | 91.94(14) | |
O1–Ag1–S1 | 105.18(5) | O1–Ag1–N2 i | 82.66(8) | 96.78(14) | |
O2–Ag1–S1 | 124.24(5) | N1–Ag1–N2 i | 164.29(10) | 169.76(12) | |
O1–Ag1–S2 i | 103.56(5) | ||||
O2–Ag1–S2 i | 121.54(5) | ||||
S1–Ag1–S2 i | 91.44(2) |
D–H···A | D–H (Å) | H···A (Å) | D···A (Å) | D–H···A (o) |
---|---|---|---|---|
Ag1 | ||||
O1–H1A···O3 i | 0.820(18) | 2.007(18) | 2.825(3) | 175(3) |
O1–H1B···O4 ii | 0.82(3) | 2.06(3) | 2.849(3) | 160(3) |
C3–H3···O1 iii | 0.95 | 2.50 | 3.428(3) | 166.6 |
C5–H5···O2 iv | 0.95 | 2.55 | 3.202(3) | 125.6 |
C5–H5···O4 v | 0.95 | 2.51 | 3.279(4) | 137.8 |
Ag2 | ||||
C1–H1···O2 ii | 0.95 | 2.43 | 3.169(4) | 134 |
C7–H7···F2 iii | 0.95 | 2.46 | 3.301(4) | 148 |
C8–H8···O3 iv | 0.95 | 2.40 | 3.299(4) | 157 |
Ag3 | ||||
O1–H1A···F1 | 0.91 | 2.12 | 2.787(7) | 129.0 |
O1–H1A···F1 ii | 0.91 | 2.11 | 2.810(7) | 133.0 |
O1–H1B···F5 | 0.92 | 2.49 | 3.121(6) | 126.6 |
O1–H1B···F5 iii | 0.92 | 2.51 | 3.084(6) | 121.2 |
C1–H1···O1 | 0.95 | 2.45 | 3.152(6) | 130.3 |
C8–H8···F5 iv | 0.95 | 2.52 | 3.141(5) | 123.0 |
Silver(I) Complex | Oxidation Process (E, V) | Reduction Processes (E, V) | |
---|---|---|---|
Ag(I)→Ag(II) | Ag(II)→Ag(I) | Ag(I)→Ag(0) | |
Ag1 | +1.25 | −0.43 | −1.26 |
Ag2 | +1.38 | −0.27 | −0.92 |
Ag3 | +1.12 | −0.19 | -0.82 |
Compound Test | tia | Ag1 | 1,8-naph | Ag2 | Ag3 | 1,5-naph | [Ag(NO3) (1,5-naph)]n | [Ag(CF3COO) (1,5-naph)]n | [Ag(CF3SO3) (1,5-naph)]n | AgSD | |
---|---|---|---|---|---|---|---|---|---|---|---|
C. albicans | µg/mL | >200 | 7.81 | >200 | 3.91 | 3.91 | >250 | 3.1 | 3.1 | 1.25 | 3.6 |
µM | >925 | 19.3 | >1537 | 10.1 | 5.0 | >1921 | 10.3 | 8.8 | 3.2 | 10 | |
C. krusei | µg/mL | >200 | 1.56 | >200 | 1.56 | 1.56 | >250 | 0.78 | 1.56 | 1.25 | 0.89 |
µM | >925 | 3.6 | >1537 | 4.0 | 1.0 | >1921 | 2.6 | 4.4 | 3.2 | 2.5 | |
C. parapsilosis | µg/mL | >200 | 3.91 | >200 | 3.91 | 7.81 | >250 | 6.25 | 3.1 | 2.5 | 0.89 |
µM | >925 | 9.7 | >1537 | 10.1 | 9.9 | >1921 | 20.8 | 8.8 | 6.5 | 2.5 | |
S. aureus | µg/mL | >250 | 3.91 | >250 | 7.81 | 7.81 | >250 | 50 | 50 | 25 | 27 |
µM | >1157 | 9.7 | >1921 | 20.2 | 9.9 | >1921 | 167 | 142 | 65 | 75 | |
L. monocytogenes | µg/mL | >250 | 15.62 | >250 | 15.62 | 125 | >250 | NT | NT | NT | NT |
µM | >1157 | 38.6 | >1921 | 40.4 | 160 | >1921 | NT | NT | NT | NT | |
E. coli | µg/mL | >250 | 15.62 | >250 | 31.25 | 15.62 | >250 | 25 | 12.5 | 12.5 | 7.14 |
µM | >1157 | 38.6 | >1921 | 80.7 | 19.8 | >1921 | 83 | 36 | 32 | 20 | |
P. aeruginosa ATCC 10332 | µg/mL | >200 | 6.25 | >200 | 3.13 | 3.13 | >250 | 25 | 25 | 25 | 8.93 |
µM | >925 | 15.5 | >1537 | 8.1 | 4.0 | >1921 | 83 | 71 | 65 | 25 | |
P. aeruginosa BK25H | µg/mL | >250 | 3.91 | >250 | 3.91 | 3.91 | >250 | NT | NT | NT | NT |
µM | >1157 | 9.7 | >1921 | 10.1 | 5.0 | >1921 | NT | NT | NT | NT | |
MRC-5 cells | µg/mL | >100 | 4.25 | >100 | 3.75 | 3.65 | >250 | NT | NT | NT | 3.6 |
µM | >462 | 10.5 | >768 | 9.7 | 4.6 | >1921 | NT | NT | NT | 10 |
Complex | Ksv (M−1) | Hypochromism (%) | Kq (M−1·s−1) | KA (M−1) | n |
---|---|---|---|---|---|
Ag1 | (1.56 ± 0.01) × 105 | 78.0 | 1.56 × 1013 | 3.05 × 106 | 1.41 |
Ag2 | (1.34 ± 0.01) × 104 | 70.2 | 1.34 × 1012 | 2.88 × 104 | 1.12 |
Ag3 | (2.70 ± 0.05) × 104 | 68.7 | 2.70 × 1012 | 6.08 × 105 | 1.37 |
Complex | Ksv (M−1) | Hypochromism (%) | Kq (M−1·s−1) | KA (M−1) | n |
---|---|---|---|---|---|
Ag1 | (7.33 ± 0.33) × 102 | 12.7 | 7.33 × 1010 | 1.05 × 102 | 0.76 |
Ag2 | (1.29 ± 0.03) × 103 | 15.2 | 1.29 × 1011 | 4.83 × 102 | 0.90 |
Ag3 | (1.15 ± 0.07) × 103 | 15.1 | 1.15 × 1011 | 4.33 × 102 | 0.88 |
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Ašanin, D.P.; Skaro Bogojevic, S.; Perdih, F.; Andrejević, T.P.; Milivojevic, D.; Aleksic, I.; Nikodinovic-Runic, J.; Glišić, B.Đ.; Turel, I.; Djuran, M.I. Structural Characterization, Antimicrobial Activity and BSA/DNA Binding Affinity of New Silver(I) Complexes with Thianthrene and 1,8-Naphthyridine. Molecules 2021, 26, 1871. https://doi.org/10.3390/molecules26071871
Ašanin DP, Skaro Bogojevic S, Perdih F, Andrejević TP, Milivojevic D, Aleksic I, Nikodinovic-Runic J, Glišić BĐ, Turel I, Djuran MI. Structural Characterization, Antimicrobial Activity and BSA/DNA Binding Affinity of New Silver(I) Complexes with Thianthrene and 1,8-Naphthyridine. Molecules. 2021; 26(7):1871. https://doi.org/10.3390/molecules26071871
Chicago/Turabian StyleAšanin, Darko P., Sanja Skaro Bogojevic, Franc Perdih, Tina P. Andrejević, Dusan Milivojevic, Ivana Aleksic, Jasmina Nikodinovic-Runic, Biljana Đ. Glišić, Iztok Turel, and Miloš I. Djuran. 2021. "Structural Characterization, Antimicrobial Activity and BSA/DNA Binding Affinity of New Silver(I) Complexes with Thianthrene and 1,8-Naphthyridine" Molecules 26, no. 7: 1871. https://doi.org/10.3390/molecules26071871