Discovery of a new class of antiviral compounds: Camphor imine derivatives

Соколова, А. С.; Yarovaya, Оlga I.; Shernyukov, Аndrey V.; Gatilov, Yuriy V.; Razumova, Yuliya V.; Zarubaev, Vladimir V.; Tretiak, Tatiana; Pokrovsky, Andrey G.; Киселев, О. И.; Salakhutdinov, N. F.

doi:10.1016/j.ejmech.2015.10.010

Cited by 85 publications

(47 citation statements)

References 44 publications

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“…The differential virucidal activities of QACs on enveloped or non-enveloped viruses were also investigated in another study [10]; the QACs tested were virucidal against enveloped Influenza A (H1N1) virus, but were ineffective against non-enveloped Poliovirus Sabin1. Several QA camphor derivatives have been evaluated against a broad range of influenza viruses [85][86][87][88]. These compounds interfered with the viral fusion process and effectively inhibited influenza virus replication in cell cultures.…”

Section: Antiviral Activitiesmentioning

confidence: 99%

Quaternary ammonium-based biomedical materials: State-of-the-art, toxicological aspects and antimicrobial resistance

Jiao

Niu

et al. 2017

Progress in Polymer Science

483

317

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a b s t r a c tMicrobial infections affect humans worldwide. Many quaternary ammonium compounds have been synthesized that are not only antibacterial, but also possess antifungal, antiviral and anti-matrix metalloproteinase capabilities. Incorporation of quaternary ammonium moieties into polymers represents one of the most promising strategies for preparation of antimicrobial biomaterials. Various polymerization techniques have been employed to prepare antimicrobial surfaces with quaternary ammonium functionalities; in particular, syntheses involving controlled radical polymerization techniques enable precise control over macromolecular structure, order and functionality. Although recent publications report exciting advances in the biomedical field, some of these technological developments have also been accompanied by potential toxicological and antimicrobial resistance challenges. Recent evidenced-based data on the biomedical applications of antimicrobial quaternary ammonium-containing biomaterials that are based on randomized human clinical trials, the golden standard in contemporary medicinal science, are included in the present review. This should help increase visibility, stimulate debates and spur conversations within a wider scientific community on the implications and plausibility for future developments of quaternary ammonium-based antimicrobial biomaterials.Published by Elsevier B.V.

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Section: Antiviral Activitiesmentioning

confidence: 99%

Quaternary ammonium-based biomedical materials: State-of-the-art, toxicological aspects and antimicrobial resistance

Jiao

Niu

et al. 2017

Progress in Polymer Science

483

317

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“…as anesthetic, muscular relaxant or insect repellent, either the compound itself or as part of natural products [23–25]. Information on the antimicrobial applications of camphor are scarce, although studies showed that camphorimine derivatives have antiviral properties against HIV [26] or influenza virus [27]. In addition, previous results obtained by us on the assessment of the antibacterial activity of camphorimine Ag(I) complexes showed that some have MIC (minimum inhibitory concentration) values considerably lower than AgNO 3 [28].…”

Section: Introductionmentioning

confidence: 99%

Ag(I) camphorimine complexes with antimicrobial activity towards clinically important bacteria and species of the Candida genus

et al. 2017

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The present work follows a previous report describing the antibacterial activity of silver camphorimine complexes of general formula [Ag(NO3)L]. The synthesis and demonstration of the antifungal and antibacterial activity of three novel [Ag(NO3)L] complexes (named 1, 2 and 3) is herein demonstrated. This work also shows for the first time that the previously studied complexes (named 4 to 8) also exert antifungal activity. The antibacterial activity of complexes was evaluated against Staphylococcus aureus, Pseudomonas aeruginosa, Burkholderia contaminans and Escherichia coli strains, while antifungal activity was tested against the Candida species C. albicans, C. glabrata, C. parapsilosis and C. tropicalis. The antimicrobial activity of the complexes ranged from very high (complex 4) to moderate (complex 6) or low (complex 8), depending on the structural and electronic characteristics of the camphorimine ligands. Notably, the highest antibacterial and anti-Candida activities do not coincide in the same complex and in some cases they were even opposite, as is the case of complex 4 which exhibits a high anti-bacterial and low antifungal activity. These distinct results suggest that the complexes may have different mechanisms against prokaryotic and eukaryotic cells. The antifungal activity of the Ag(I) camphorimine complexes (in particular of complex 1) was found to be very high (MIC = 2 μg/mL) against C. parapsilosis, being also registered a prominent activity against C. tropicalis and C. glabrata. None of the tested compounds inhibited C. albicans growth, being this attributed to the ability of these yeast cells to mediate the formation of less toxic Ag nanoparticles, as confirmed by Scanning Electron Microscopy images. The high antibacterial and anti-Candida activities of the here studied camphorimine complexes, especially of complexes 1 and 7, suggests a potential therapeutic application for these compounds.

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“…Its activity was based on specific inhibition of viral hemagglutinin. Further it was shown that analogs of camphecene are also of high activity against influenza virus . Our libraries included amino‐ and imino‐derivatives of camphor.…”

Section: Resultsmentioning

confidence: 99%

“…It was shown previously that a product resulting from the reaction of camphor and aminoethanol and called camphecene exhibits a wide spectrum of antiviral activity and low toxicity . Recently, we prepared a new series of compounds derived from camphecene showing expressed antiviral activity .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Camphecene and Cytisine Conjugates Using Click Chemistry Methodology and Study of Their Antiviral Activity

Аrtyushin

Moiseeva

Zarubaev

et al. 2019

Chemistry & Biodiversity

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A series of camphecene and quinolizidine alkaloid (−)‐cytisine conjugates has been obtained for the first time using ‘click’ chemistry methodology. The cytotoxicity and virus‐inhibiting activity of compounds were determined against MDCK cells and influenza virus A/Puerto Rico/8/34 (H1N1), correspondingly, in in vitro tests. Based on the results obtained, values of 50 % cytotoxic dose (CC50), 50 % inhibition dose (IC50) and selectivity index (SI) were determined for each compound. It has been shown that the antiviral activity is affected by the length and nature of linkers between cytisine and camphor units. Conjugate 13 ((1R,5S)‐3‐(6‐{4‐[(2‐{(E)‐[(1R,4R)‐1,7,7‐trimethylbicyclo[2.2.1]heptan‐2‐ylidene]amino}ethoxy)methyl]‐1H‐1,2,3‐triazol‐1‐yl}hexyl)‐1,2,3,4,5,6‐hexahydro‐8H‐1,5‐methanopyrido[1,2‐a][1,5]diazocin‐8‐one), which contains cytisine fragment separated from triazole ring by –C6H12– aliphatic linker, showed the highest activity at relatively low toxicity (CC50=168 μmol, IC50=8 μmol, SI=20). Its selectivity index appeared higher than that of reference compound, rimantadine. According to theoretical calculations, the antiviral activity of the lead compound 13 can be explained by its influence on the functioning of neuraminidase.

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Discovery of a new class of antiviral compounds: Camphor imine derivatives

Cited by 85 publications

References 44 publications

Quaternary ammonium-based biomedical materials: State-of-the-art, toxicological aspects and antimicrobial resistance

Quaternary ammonium-based biomedical materials: State-of-the-art, toxicological aspects and antimicrobial resistance

Ag(I) camphorimine complexes with antimicrobial activity towards clinically important bacteria and species of the Candida genus

Synthesis of Camphecene and Cytisine Conjugates Using Click Chemistry Methodology and Study of Their Antiviral Activity

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