Dichlorophen
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Category | Antibiotics |
Catalog number | BBF-05908 |
CAS | 97-23-4 |
Molecular Weight | 269.12 |
Molecular Formula | C13H10Cl2O2 |
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Description
Dichlorophen is an antimicrobial agent with activity against cestodes, protozoa, fungi, and bacteria.
Specification
Synonyms | dichlorophene; 2,2'-Methylenebis(4-chlorophenol); Dichlorofen |
IUPAC Name | 4-chloro-2-[(5-chloro-2-hydroxyphenyl)methyl]phenol |
Canonical SMILES | C1=CC(=C(C=C1Cl)CC2=C(C=CC(=C2)Cl)O)O |
InChI | InChI=1S/C13H10Cl2O2/c14-10-1-3-12(16)8(6-10)5-9-7-11(15)2-4-13(9)17/h1-4,6-7,16-17H,5H2 |
InChI Key | MDNWOSOZYLHTCG-UHFFFAOYSA-N |
Properties
Antibiotic Activity Spectrum | Bacteria; Fungi; Parasites |
Reference Reading
1. Drug repurposing for the treatment of alveolar echinococcosis: in vitro and in vivo effects of silica nanoparticles modified with dichlorophen
Julia Fabbri, Patricia E Pensel, Clara M Albani, Valeria B Arce, Daniel O Mártire, María C Elissondo Parasitology. 2019 Nov;146(13):1620-1630. doi: 10.1017/S0031182019001057. Epub 2019 Aug 28.
Alveolar echinococcosis is a neglected parasitic zoonosis caused by the metacestode Echinococcus multilocularis, which grows as a malignant tumour-like infection in the liver of humans. Albendazole (ABZ) is the antiparasitic drug of choice for the treatment of the disease. However, its effectiveness is low, due to its poor absorption from the gastro-intestinal tract. It is also parasitostatic and in some cases produces side-effects. Therefore, an alternative to the treatment of this severe human disease is necessary. In this context, the repositioning of drugs combined with nanotechnology to improve the bioavailability of drugs emerges as a useful, fast and inexpensive tool for the treatment of neglected diseases. The in vitro and in vivo efficacy of dichlorophen (DCP), an antiparasitic agent for intestinal parasites, and silica nanoparticles modified with DCP (NP-DCP) was evaluated against E. multilocularis larval stage. Both formulations showed a time and dose-dependent in vitro effect against protoscoleces. The NP-DCP had a greater in vitro efficacy than the drug alone or ABZ. In vivo studies demonstrated that the NP-DCP (4 mg kg-1) had similar efficacy to ABZ (25 mg kg-1) and greater activity than the free DCP. Therefore, the repurposing of DCP combined with silica nanoparticles could be an alternative for the treatment of echinococcosis.
2. Experimental and theoretical study on Fe(VI) oxidative degradation of dichlorophen in water: Kinetics and reaction mechanisms
Yi Fei, Zhuangzhuang Liu, Liang Meng, Guoqiang Liu, Deyang Kong, Xiaoxue Pan, Feng Zhu, Junhe Lu, Jing Chen Environ Pollut. 2022 Aug 1;306:119394. doi: 10.1016/j.envpol.2022.119394. Epub 2022 May 4.
Dichlorophenol (DCP), a commonly used fungicide and insecticide, is widely found in waters and wastewaters. Herein, the degradation of DCP by Ferrate (Fe(VI)) in different matrices was comprehensively investigated. In pure water, a complete removal of DCP was achieved in 300 s at [Fe(VI)]:[DCP] molar ratio of 2:1. The presence of HA (10 mg L-1) inhibited DCP degradation to a certain extent. A total of twenty degradation products were identified by HPLC/MS analysis. Based on these products, reaction pathways including the cleavage of C-C bridge bond, hydroxylation, and radical coupling were proposed. These reaction mechanisms were further rationalized by theoretical calculations. The analyses of Wiberg bond orders and transition state indicated that C7-C8 bond was the most vulnerable site for cleavage, and C12 site was the most likely site for hydroxyl addition. Mulliken atomic spin densities distribution suggested that self-coupling products was easily generated via C-O-C coupling ways. Finally, the feasibility of applying Fe(VI) to degrade DCP (20 μM) in a municipal wastewater effluent and a lake water was evaluated and verified. The findings in this study are of relevance in designing Fe(VI)-based treatment strategy for chlorine-containing persistent pesticides.
3. Identification of Bithionol, Dichlorophen, and Miconazole as Antibacterial Agents against Acinetobacter calcoaceticus
Tiffany H Khaw, S N Michael Wong, Genevieve Herle, Jean Patrick Gonzalez Dahua, Adhitya Logan, Saleem Alameh, Mikhail Martchenko Shilman, Anastasia Levitin ACS Omega. 2020 Sep 8;5(37):23951-23959. doi: 10.1021/acsomega.0c03211. eCollection 2020 Sep 22.
The rising prevalence of multidrug-resistant hospital-acquired infections has increased the need for new antibacterial agents. In this study, a library of 1586 FDA-approved drugs was screened against A. calcoaceticus, a representative of the Acinetobacter calcoaceticus-baumannii complex. Three compounds were found to have previously undiscovered antibacterial properties against A. calcoaceticus: antifungal Miconazole, anthelminthic Dichlorophen, and Bithionol. These three drugs were tested against a wide range of Gram-positive and Gram-negative bacteria and confirmed to have broad-spectrum antibacterial properties. Combinations of these three drugs were also tested against the same bacteria, and two novel combination therapies with synergistic effects were discovered. In the future, antibacterial properties of these three drugs and two combination therapies will be evaluated against pathogenic bacteria using an animal model.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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