A Review of the Biological Activity of Amidrazone Derivatives
Abstract
:1. Introduction
2. Results
2.1. Antimicrobial Activity
2.1.1. Tuberculostatic Activity
2.1.2. Antibacterial Activity
2.1.3. Antifungal Activity
2.2. Antiparasitic Activity
2.3. Antiviral Activity
2.4. Anti-Inflammatory Activity
2.5. Cytoprotective Activity
2.6. Antitumor Activity
Comp. | IC50 MCF-7 | IC50 K562 | Ref. |
---|---|---|---|
69 | 2.50 µM | 3.10 µM | [69] |
70 | 2.70 µM | 3.50 µM | [69] |
71 | 7.26 µM | 9.91 µM | [70] |
72 | >50 µM | 1.02 µM | [71] |
73 | 5.18 µM | 2.89 µM | [72] |
74 | 5.91 µM | 5.02 µM | [73] |
75 | 20.20 µM | 9.30 µM | [74] |
76 | 4.50 µM | 1.10 µM | [75] |
79 | 4.30 µM | 3.00 µM | [77] |
81 | 0.09 µM | - | [78] |
2.7. Furin Inhibition
2.8. Acetylocholinesterase Inhibition
3. Summary
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Abbreviations
AChE | acetylcholinesterase |
BChE | butyrylocholinesterase |
CNS | central nervous system |
COX | cyclooxygenase |
EC50 | half maximal effective concentration |
HIV-RT | HIV reverse transcriptase |
IC50 | half-maximal inhibitory concentration |
IL-6 | interleukin-6 |
LD50 | dose which causes the death of 50% of a group of test animals |
LPS | lipopolysaccharide |
MBC | minimal bactericidal concentration |
MIC | minimal inhibitory concentration |
MRSA | methicillin-resistant Staphylococcus aureus |
MSSA | methicillin-susceptible Staphylococcus aureus |
PBMC | peripheral blood mononuclear cell |
TNF-α | tumor necrosis factor |
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Comp. | IC50 AChE [µM] | IC50 BChE [µM] | Ref. |
---|---|---|---|
75 | 24.25 ± 2.97 | 0.002 ± 0.0014 | [91] |
94 | 17.95 ± 0.90 | 17.51 ± 0.21 | [92] |
95 | 28.16 ± 0.98 | 1.69 ± 0.17 | [92] |
96 | 24.75 ± 0.17 | >500 | [92] |
tacrine | 0.124 ± 0.02 | 7.8 ± 0.06 | [91] |
rivastigmine | 56.10 ± 1.41 | 38.40 ± 1.97 | [92] |
Comp. | Activity | Animal Model | Dose | Effect | Reference Drug | Ref. |
---|---|---|---|---|---|---|
23 | anti-inflammatory | xylene-induced ear edema test in mice | 100 mg/kg | 92.45% edema reduction | indomethacin 89.38% reduction, ibuprofen 87.36% reduction | [25] |
25 | anti-inflammatory | xylene-induced ear edema test in mice | 50 mg/kg | 93.56% edema reduction | indomethacin 45.23% reduction, ibuprofen 29.56% reduction | [26] |
26 | 50 mg/kg | 81.65% edema reduction | ||||
30 | antibacterial | MRSA-infected C. elegans | 20 mg/mL | reduction in the MRSA burden by ~90% | vancomycin ~90% reduction | [30] |
MRSA murine skin infection | 2% suspension | 73% reduction in MRSA burden | fusidic acid 78% reduction | |||
MRSA-infected mice | 20 mg/kg | 77% reduction in MRSA burden | vancomycin 66% reduction | |||
31 | MRSA-infected C. elegans | 20 mg/mL | reduction in the MRSA burden by ~90% | vancomycin ~90% reduction | ||
MRSA murine skin infection | 2% suspension | 71% reduction in MRSA burden | fusidic acid 78% reduction | |||
55 | anti-inflammatory | carrageenan-induced rat hind paw edema | 21 mg/kg | 65–73% edema reduction (0.5–2 h) | diclofenac 50–58% edema reduction (0.5–8 h) | [50] |
42 mg/kg | 38–60% edema reduction (0.5–2 h) | |||||
antinociceptive | hot-plate test in mice | 21 mg/kg | analgesic effect (0.5–2 h) | morphine analgesic effect(0.5–1 h) | ||
42 mg/kg | analgesic effect (0.5–2 h) | |||||
60 | anti-inflammatory | carrageenan-induced rat hind paw edema | 65 mg/kg | 89.3% edema reduction | indomethacin 46% edema reduction | [55] |
61 | 65 mg/kg | 87.7% edema reduction | ||||
62 | 61 mg/kg | 80.7% edema reduction | ||||
63 | 61 mg/kg | 79.5% edema reduction | ||||
65 | anti-inflammatory neonatal sepsis treatment | LPS-induced sepsis in neonatal mice | 50 mg/kg | reduction in anxiety-like behavior and cognitive disorders in adult life | - | [58] |
Comp. | Activity | Mechanism | Ref. |
---|---|---|---|
AG | anti-inflammatory | suppression of oxidative stress, inhibition of IL-1β, IL-6, and Foxp3 mRNA upregulation | [57] |
1 | antituberculosic | inhibiting protein synthesis via direct binding to the bacterial ribosomal subunit | [15] |
8 | antibacterial | inhA inhibition | [19] |
27 | antibacterial | inhibition of DHFR protein | [27] |
28 | antibacterial | interaction with E. coli FabH-CoA receptor. | [28] |
29 | antibacterial | interaction with β-ketoacyl-ACP synthase III (FabH) | [29] |
30 | antibacterial | inhibitor of undecaprenyl diphosphate phosphatase and undecaprenyl diphosphate | [30] |
38–39 | antifungal | interaction with DNA (intercalation) | [37] |
43 | antifungal | inhibition of 14-α-demethylase (CYP51) | [40] |
46 | antigiardial | inhibition of adherence of trophozoides | [42] |
47 | cytoprotective | inhibition of R15A, inhibition of dephosphorylation of enzyme eIF2α | [59] |
48 | cytoprotective | inhibition of R15B, inhibition of dephosphorylation of enzyme eIF2α | [66] |
48–50 | antiparasitic | binding trypanothione reductase enzyme | [45] |
53 | antiviral | inhibition of HIV-RT | [48] |
54 | anti-inflammatory | decreasing production of TNF-α | [49] |
55 | anti-inflammatory | decreasing production of IL-6 | [50] |
56 | anti-inflammatory | decreasing production of TNF-α | [51] |
57 | anti-inflammatory | G1 phase arrest | [52] |
58 | anti-inflammatory | decreasing production of IL-6 | [54] |
60–63 | anti-inflammatory | inhibition of COX-1 and COX-2 | [55] |
64 | antarthritic | inhibition expression of ASIC1a protein | [56] |
65 | anti-inflammatory | inhibition of NFκB activation | [58] |
66 | cytoprotective | inhibition of R15A, inhibition of dephosphorylation of enzyme eIF2α | [59] |
72 | antitumor | tyrosine kinase brc-abl inhibitor | [71] |
73 | antitumor | tyrosine kinase brc-abl inhibitor | [72] |
74 | antitumor | tyrosine kinase brc-abl inhibitor | [73] |
75 | antitumor | tyrosine kinase brc-abl inhibitor | [74] |
76 | antitumor | tyrosine kinase brc-abl inhibitor | [75] |
79 | antitumor | phosphatidylinositol 3-kinase inhibitor | [77] |
81 | antitumor | inhibition of tubulin polymerization, colchicine binding | [78] |
82 | antitumor | inhibition of ribosomal kinase RSK2 | [79] |
92 | enzyme inhibition | furin inhibitor, trypsin inhibitor | [89] |
93 | enzyme inhibition | furin inhibitor, thrombin inhibitor | [89] |
75 | enzyme inhibition | BChE inhibitor | [91] |
94 | enzyme inhibition | AChE and BChE inhibitor | [92] |
95–96 | enzyme inhibition | BChE inhibitor | [92] |
Comp. | Animal Model | Time | Toxicity | Ref. |
18 | brine shrimp | 24 h | IC50 > 50 µg/mL | [23] |
19 | brine shrimp | 24 h | IC50 > 50 µg/mL | [23] |
20 | brine shrimp | 24 h | IC50 > 12.5 µg/mL | [23] |
21 | brine shrimp | 24 h | IC50 > 12.5 µg/mL | [23] |
43 | zebrafish embryos | 96 h | LC50 = 8.2 µg/mL | [40] |
55 | Swiss mice | - | LD50 = 417 mg/kg | [50] |
78 | brine shrimp | 24 h | IC50 > 50 µg/mL | [23] |
Comp. | Studied cells | Origin | Toxicity | Ref. |
2 | Vero | monkey | IC50 = 28.7 µM | [17] |
3 | Vero | monkey | IC50 = 23.1 µM | [17] |
4 | Vero | monkey | IC50 = 27.8 µM | [17] |
5 | Vero | monkey | IC50 = 298 µM | [17] |
6 | fibroblasts | human | IC50 = 10.39 µg/mL | [18] |
7 | fibroblasts | human | IC50 = 3.29 µg/mL | [18] |
28 | HEK 293T | human | IC50 = 56.39 µmol/L | [28] |
32 | fibroblasts | mice | IC50 = 41.8 µg/mL | [31] |
43 | MRC-5 | human | IC50 = 2.5 µg/mL | [40] |
23 | LO2 | human | IC50 = 18.1 µg/mL | [25] |
30–31 | HRT-18 | human | IC50 > 32 µg/mL | [30] |
44 | macrophages | mice | IC50 = 79.59 µM | [41] |
45 | macrophages | mice | IC50 = 423.33 µM | [41] |
46 | RAW264.7 | mice | IC50 = 17.1 µM | [42] |
48–50 | J774.A1 | mice | IC50 > 10 μM | [45] |
51 | PBMC | human | IC50 > 100 µg/mL | [46] |
54 | PBMC | human | IC50 > 100 µg/mL | [49] |
56 | PBMC | human | IC50 > 10 µg/mL | [51] |
57 | PBMC | human | IC50 > 50 µg/mL | [52] |
58–59 | PBMC | human | IC50 > 100 µg/mL | [54] |
64 | chondrocytes | rat | IC50 > 25 µM | [56] |
72 | fibroblasts | human | IC50 > 50 µM | [71] |
76 | fibroblasts | human | IC50 = 15 µM | [75] |
83 | Vero | monkey | IC50 > 100 µM | [80] |
87 | Vero | monkey | IC50 > 611.09 µM | [84] |
88 | ARPE-19 | human | IC50 = 38.82 µM | [85] |
89 | ARPE-19 | human | IC50 = 41.23 µM | [85] |
90 | MRC-5 | human | IC50 = 58.9 µM | [86] |
91 | PBMC | human | IC50 > 25 µg/mL | [49] |
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Paprocka, R.; Wiese-Szadkowska, M.; Kosmalski, T.; Frisch, D.; Ratajczak, M.; Modzelewska-Banachiewicz, B.; Studzińska, R. A Review of the Biological Activity of Amidrazone Derivatives. Pharmaceuticals 2022, 15, 1219. https://doi.org/10.3390/ph15101219
Paprocka R, Wiese-Szadkowska M, Kosmalski T, Frisch D, Ratajczak M, Modzelewska-Banachiewicz B, Studzińska R. A Review of the Biological Activity of Amidrazone Derivatives. Pharmaceuticals. 2022; 15(10):1219. https://doi.org/10.3390/ph15101219
Chicago/Turabian StylePaprocka, Renata, Małgorzata Wiese-Szadkowska, Tomasz Kosmalski, Daria Frisch, Magdalena Ratajczak, Bożena Modzelewska-Banachiewicz, and Renata Studzińska. 2022. "A Review of the Biological Activity of Amidrazone Derivatives" Pharmaceuticals 15, no. 10: 1219. https://doi.org/10.3390/ph15101219
APA StylePaprocka, R., Wiese-Szadkowska, M., Kosmalski, T., Frisch, D., Ratajczak, M., Modzelewska-Banachiewicz, B., & Studzińska, R. (2022). A Review of the Biological Activity of Amidrazone Derivatives. Pharmaceuticals, 15(10), 1219. https://doi.org/10.3390/ph15101219