Unsubstituted Oximes as Potential Therapeutic Agents

Surowiak, Alicja Karolina; Lochyński, Stanisław; Strub, Daniel

doi:10.3390/sym12040575

Cited by 24 publications

(12 citation statements)

References 49 publications

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“…In plants, oximes and their derivatives play a fundamental role in the metabolism of plant growth and development and in a variety of biosynthetic pathways [ 9 , 11 ]. In animals, oximes are most commonly known for their participation in the olfactory communication between animals [ 12 ]. Oximes exist as colorless crystals, are poorly soluble in water, and are easily accessible in laboratories and in industry, which makes them very appealing [ 13 , 14 ].…”

Section: Chemistry Of Steroidal Oximesmentioning

confidence: 99%

The Structural Diversity and Biological Activity of Steroid Oximes

et al. 2023

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Steroids and their derivatives have been the subject of extensive research among investigators due to their wide range of pharmacological properties, in which steroidal oximes are included. Oximes are a chemical group with the general formula R1R2C=N−OH and they exist as colorless crystals and are poorly soluble in water. Oximes can be easily obtained through the condensation of aldehydes or ketones with various amine derivatives, making them a very interesting chemical group in medicinal chemistry for the design of drugs as potential treatments for several diseases. In this review, we will focus on the different biological activities displayed by steroidal oximes such as anticancer, anti-inflammatory, antibacterial, antifungal and antiviral, among others, as well as their respective mechanisms of action. An overview of the chemistry of oximes will also be reported, and several steroidal oximes that are in clinical trials or already used as drugs are described. An extensive literature search was performed on three main databases—PubMed, Web of Science, and Google Scholar.

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Section: Chemistry Of Steroidal Oximesmentioning

confidence: 99%

The Structural Diversity and Biological Activity of Steroid Oximes

et al. 2023

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“…Oximes constitute a very important class of compounds in plants and serve as key players in the metabolism and a variety of biosynthetic pathways [11,12]. A wide range of oximes are found in plants and several structurally diverse oximes are involved in the metabolism of plant growth and development.…”

Section: The Sources and Discovery Of Oximesmentioning

confidence: 99%

“…Pralidoxime chloride is synthesized, as shown in the synthetic Scheme 1 [83]. The first step involves the treatment of pyridine-2-carboxaldehyde (12) with hydroxylamine hydrochloride to obtain an aldoxime intermediate 13. The resulting oxime ( 13) is further methylated using a corresponding methylation agent, to obtain N-methylated-pyridinium intermediate (14).…”

Section: Pralidoximementioning

confidence: 99%

FDA-Approved Oximes and Their Significance in Medicinal Chemistry

2022

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Despite the scientific advancements, organophosphate (OP) poisoning continues to be a major threat to humans, accounting for nearly one million poisoning cases every year leading to at least 20,000 deaths worldwide. Oximes represent the most important class in medicinal chemistry, renowned for their widespread applications as OP antidotes, drugs and intermediates for the synthesis of several pharmacological derivatives. Common oxime based reactivators or nerve antidotes include pralidoxime, obidoxime, HI-6, trimedoxime and methoxime, among which pralidoxime is the only FDA-approved drug. Cephalosporins are β-lactam based antibiotics and serve as widely acclaimed tools in fighting bacterial infections. Oxime based cephalosporins have emerged as an important class of drugs with improved efficacy and a broad spectrum of anti-microbial activity against Gram-positive and Gram-negative pathogens. Among the several oxime based derivatives, cefuroxime, ceftizoxime, cefpodoxime and cefmenoxime are the FDA approved oxime-based antibiotics. Given the pharmacological significance of oximes, in the present paper, we put together all the FDA-approved oximes and discuss their mechanism of action, pharmacokinetics and synthesis.

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“…The research carried out so far focused mainly on synthetic aspects of oximes 14 , 15 , and there are only few references related to the antimicrobial activity of this class of compounds. Some higher molecular weight oximes were tested on some microorganisms and were found to be effective, yet the mechanism of the observed antimicrobial activity is still not entirely clear 16 .…”

Section: Introductionmentioning

confidence: 99%

Cytotoxicity, early safety screening, and antimicrobial potential of minor oxime constituents of essential oils and aromatic extracts

Surowiak

Sowała

Talma

et al. 2022

Sci Rep

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Due to market and legislative expectations, there is a constant need to explore new potential antimicrobial agents for functional perfumery. In this study, we evaluated the antimicrobial activity of 53 low molecular oximes and the corresponding carbonyl compounds against Escherichia coli, Enterococcus hirae, Pseudomonas aeruginosa, Bacillus cereus, Staphylococcus aureus, Aspergillus brasiliensis, Legionella pneumophila and Candida albicans. The most potent compound was α-isomethylionone oxime, which exhibited a minimum inhibitory concentration (MIC) of 18.75 µg/mL against E. hirae. The evaluation of the MICs for bacterial and fungal strains was performed for selected compounds, for example, the MIC of 2-phenylpropionaldehyde, cis-jasmone oxime, and trans-cinnamaldehyde measured against A. brasiliensis was 37.50 µg/mL. ADME-Tox (Absorption, Distribution, Metabolism, Excretion, and Toxicity) and 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium (MTS) cell viability assays were performed to assess the cytotoxicity of tested compounds. ADME-Tox indicated the safety and promising properties of selected compounds, which enables their usage as nontoxic supporting antibacterial agents. The results of the in vitro MTS assay were consistent with the ADME-Tox results. None of the compounds tested was toxic to Human Embryonic Kidney 293T (HEK293T) cells, with all cell viabilities exceeding 85%.

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Unsubstituted Oximes as Potential Therapeutic Agents

Cited by 24 publications

References 49 publications

The Structural Diversity and Biological Activity of Steroid Oximes

The Structural Diversity and Biological Activity of Steroid Oximes

FDA-Approved Oximes and Their Significance in Medicinal Chemistry

Cytotoxicity, early safety screening, and antimicrobial potential of minor oxime constituents of essential oils and aromatic extracts

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