Broad range of inhibiting action of novel camphor-based compound with anti-hemagglutinin activity against influenza viruses in vitro and in vivo

Zarubaev, Vladimir V.; Гаршинина, А В; Tretiak, Tatiana; Fedorova, V. A.; Штро, Анна А.; Соколова, А. С.; Yarovaya, Оlga I.; Salakhutdinov, N. F.

doi:10.1016/j.antiviral.2015.06.004

Cited by 65 publications

(45 citation statements)

References 24 publications

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“…Acetylene block, camphecene propargyl ether 9 , was obtained in one stage by the Williamson reaction via described procedure using propargyl bromide and camphecene alkoxylate obtained in situ by reacting camphecene with sodium hydride in toluene.…”

Section: Resultsmentioning

confidence: 99%

“…Compound 17 , like conjugates 11 – 13 , were prepared by click chemistry methodology using as azide building block azide 16 obtained by us previously by the alkylation of cytisine with propargyl bromide . Compound 18 with ethylene spacer was obtained by the reaction of cytisine with sulfonate 15 using previously described procedure …”

Section: Resultsmentioning

confidence: 99%

“…Previously, we synthesized and studied series of camphor‐based derivatives. Among them, camphecene (1,7,7‐trimethylbicyclo[2.2.1]heptan‐2‐ylidene‐aminoethanol) appeared to be the most active compound . Its activity was based on specific inhibition of viral hemagglutinin.…”

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%

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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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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

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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“…Mice were weighed and euthanized at 5 dpi, and the lungs were removed and weighed53. The lung index was calculated as follows using the obtained values: Lung index = A/B × 100, where A is the lung weight, and B is the body weight54.…”

Section: Methodsmentioning

confidence: 99%

Antiviral activity of chlorogenic acid against influenza A (H1N1/H3N2) virus and its inhibition of neuraminidase

Ding

Cao

et al. 2017

Sci Rep

158

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Lonicera japonica Thunb, rich in chlorogenic acid (CHA), is used for viral upper respiratory tract infection treatment caused by influenza virus, parainfluenza virus, and respiratory syncytial virus, ect in China. It was reported that CHA reduced serum hepatitis B virus level and death rate of influenza virus-infected mice. However, the underlying mechanisms of CHA against the influenza A virus have not been fully elucidated. Here, the antiviral effects and potential mechanisms of CHA against influenza A virus were investigated. CHA revealed inhibitory against A/PuertoRico/8/1934(H1N1) (EC50 = 44.87 μM), A/Beijing/32/92(H3N2) (EC50 = 62.33 μM), and oseltamivir-resistant strains. Time-course analysis showed CHA inhibited influenza virus during the late stage of infectious cycle. Indirect immunofluorescence assay indicated CHA down-regulated the NP protein expression. The inhibition of neuraminidase activity confirmed CHA blocked release of newly formed virus particles from infected cells. Intravenous injection of 100 mg/kg/d CHA possessed effective antiviral activity in mice, conferring 60% and 50% protection from death against H1N1 and H3N2, reducing virus titres and alleviating inflammation in the lungs effectively. These results demonstrate that CHA acts as a neuraminidase blocker to inhibit influenza A virus both in cellular and animal models. Thus, CHA has potential utility in the treatment of the influenza virus infection.

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Stability study of the antiviral agent camphecene in dried blood spots at different temperatures

Okhina

Rogachev

Yarovaya

et al. 2021

Drug Testing and Analysis

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In this study, an optimized procedure of sample preparation for quantitative determination of the antiviral agent camphecene in dried rat blood spots was developed. It has been shown that when using methanol containing 0.1% HCOOH as an extractant, the recovery of the substance increases in comparison with the previously developed method. In addition to this, there is no need to dilute the obtained solutions with water for the analysis of the sample by high‐performance liquid chromatography (HPLC) on a column with a reversed‐phase sorbent. By using the developed method, the stability of samples of dried rat blood spots containing camphecene in different concentrations at different temperatures was studied. It was found that while the samples were stored at room temperature, apparently, desorption of the substance occurs leading to a loss of more than 15% of its initial amount after 5–10 days. Lowering the temperature increases the stability of samples and their storage at −70°C is possible for 4 weeks.

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Broad range of inhibiting action of novel camphor-based compound with anti-hemagglutinin activity against influenza viruses in vitro and in vivo

Cited by 65 publications

References 24 publications

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

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

Antiviral activity of chlorogenic acid against influenza A (H1N1/H3N2) virus and its inhibition of neuraminidase

Stability study of the antiviral agent camphecene in dried blood spots at different temperatures

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