Synthesis of erythrodiol C-ring derivatives and their activity against Chlamydia trachomatis

Казакова, О. Б.; Rubanik, Liudmila; Лобов, А. Н.; Poleshchuk, N. N.; Байкова, И. П.; Kapustina, Yuliya; Petrova, А. V.; Korzun, Tatyana; Lopatina, T. V.; Fedorova, Alexandra A.; Рыбалова, Т. В.; Половяненко, Д.Н.; Mioc, Marius; Şoica, Codruţa

doi:10.1016/j.steroids.2021.108912

Cited by 10 publications

(6 citation statements)

References 29 publications

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“…In the spectrum, the download shift of the signal of carbon atom in the C3 position from δ 59.7 ppm (for compound 21 [ 38 ]) to 61.1 ppm ( 13 C NMR) was observed; the signals of the CONH group, at δ 169.5 ppm ( 13 C NMR), and the signals of the phthalic fragment at δ 134.0, were located at 123.0 ppm ( 13 C NMR) and 7.61–7.90 ppm ( 1 H NMR), respectively, while a free carboxylic group was located at δ 169.2 ppm ( 13 C NMR) ( Supplementary Material Figures S33, S34 ). The compound 23 was obtained according to [ 35 ].…”

Section: Resultsmentioning

confidence: 99%

“…The oleanolic acid was purchased in Xi’an Rongsheng Biotechnology Co Ltd. (ISO9001:2008 and GMP certified company). Compounds 5 [ 26 ], 13 and 14 [ 37 ], 21 [ 38 ], 23 [ 35 ] were obtained according to the methods described previously.…”

Section: Methodsmentioning

confidence: 99%

“…Therefore, taking into account the high potency of OA as an antibacterial and antiviral scaffold [ 26 , 34 , 35 ], we present a synthesis of new oleanonic, 2,3-indolo-and 2-pyridinoylidene-oleanonic acids dipeptides and conjugates with some linear and cyclic polyamines, as well as a screening of their antiviral activity against influenza A (H1N1) and all serotypes of Dengue virus.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

et al. 2022

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A series of sixteen A-ring modified (2,3-indolo-, 2-benzylidene) oleanonic acid derivatives, holding some cyclic amines, linear polyamines and benzylaminocarboxamides at C28, has been synthesized and screened for antiviral activity against influenza A/PuertoRico/8/34 (H1N1) and Dengue virus serotypes of DENV-1, -2, -3, -4. It was found that 28-homopiperazine 2 and 3-N-phthalyl 22 amides of oleanonic acid demonstrated high potency with selectivity index SI 27 (IC50 21 μM) and 42 (IC50 12 μM). Oleanonic acid aminoethylpiperazine amide 6 and C-azepano-erythrodiol 23 appeared to be the most effective compounds against DENV-1 (IC50′s 67 and 107 μM) and -2 (IC50′s 86 and 68 μM correspondingly) serotypes.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

et al. 2022

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“…Despite their better in vitro potency, the effects of maniladiol and erythrodiol against cancer models have been poorly investigated. Interest seems to be turned onto some less hydrophobic derivatives [ 142 , 143 , 144 ]. Noteworthy, the introduction of an oxygen substituent into the C-ring increases the biological activities, including cytotoxic effects [ 145 ].…”

Section: Discussionmentioning

confidence: 99%

Systematic Review of Potential Anticancerous Activities of Erythrina senegalensis DC (Fabaceae)

Fofana

Ouédraogo

Esposito

et al. 2021

Plants

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The objective of this study was to carry out a systematic review of the substances isolated from the African medicinal plant Erythrina senegalensis, focusing on compounds harboring activities against cancer models detailed in depth herein at both in vitro and in vivo preclinical levels. The review was conducted through Pubmed and Google Scholar. Nineteen out of the forty-two secondary metabolites isolated to date from E. senegalensis displayed interesting in vitro and/or in vivo antitumor activities. They belonged to alkaloid (Erysodine), triterpenes (Erythrodiol, maniladiol, oleanolic acid), prenylated isoflavonoids (senegalensin, erysenegalensein E, erysenegalensein M, alpinumisoflavone, derrone, warangalone), flavonoids (erythrisenegalone, senegalensein, lupinifolin, carpachromene) and pterocarpans (erybraedine A, erybraedine C, phaseollin). Among the isoflavonoids called “erysenegalensein”, only erysenealenseins E and M have been tested for their anticancerous properties and turned out to be cytotoxic. Although the stem bark is the most frequently used part of the plant, all pterocarpans were isolated from roots and all alkaloids from seeds. The mechanisms of action of its metabolites include apoptosis, pyroptosis, autophagy and mitophagy via the modulation of cytoplasmic proteins, miRNA and enzymes involved in critical pathways deregulated in cancer. Alpinumisoflavone and oleanolic acid were studied in a broad spectrum of cancer models both in vitro and in preclinical models in vivo with promising results. Other metabolites, including carpachromen, phaseollin, erybraedin A, erysenegalensein M and maniladiol need to be further investigated, as they display potent in vitro effects.

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“…Additionally, Hwang et al, optimized peptide-based inhibitors (2-Pyridone-based analogs) in order to better target HtrA serine protease in Ct, an enzyme essential to several bacterial vital functions, which seems to be a promising strategy [ 97 ]. Finally, Kazakova and colleagues have defended the need for further research to investigate the promising role ofC-ring oxygen and nitrogen erythrodiol derivatives against Ct infections [ 98 ].…”

Section: Treatment Failure and Novel Approachesmentioning

confidence: 99%

Therapeutic Options for Chlamydia trachomatis Infection: Present and Future

et al. 2022

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Sexually transmitted infections (STIs), such as Chlamydia trachomatis (Ct) infection, have serious consequences for sexual and reproductive health worldwide. Ct is one of the most common sexually transmitted bacterial infections in the world, with approximately 129 million new cases per year. C. trachomatis is an obligate intracellular Gram-negative bacterium. The infection is usually asymptomatic, notwithstanding, it could also be associated with severe sequels and complications, such as chronic pain, infertility, and gynecologic cancers, and thus there is an urgent need to adequately treat these cases in a timely manner. Consequently, beyond its individual effects, the infection also impacts the economy of the countries where it is prevalent, generating a need to consider the hypothesis of implementing Chlamydia Screening Programs, a decision that, although it is expensive to execute, is a necessary investment that unequivocally will bring financial and social long-term advantages worldwide. To detect Ct infection, there are different methodologies available. Nucleic acid amplification tests, with their high sensitivity and specificity, are currently the first-line tests for the detection of Ct. When replaced by other detection methods, there are more false negative tests, leading to underreported cases and a subsequent underestimation of Ct infection’s prevalence. Ct treatment is based on antibiotic prescription, which is highly associated with drug resistance. Therefore, currently, there have been efforts in line with the development of alternative strategies to effectively treat this infection, using a drug repurposing method, as well as a natural treatment approach. In addition, researchers have also made some progress in the Ct vaccine development over the years, despite the fact that it also necessitates more studies in order to finally establish a vaccination plan. In this review, we have focused on the therapeutic options for treating Ct infection, expert recommendations, and major difficulties, while also exploring the possible avenues through which to face this issue, with novel approaches beyond those proposed by the guidelines of Health Organizations.

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Synthesis of erythrodiol C-ring derivatives and their activity against Chlamydia trachomatis

Cited by 10 publications

References 29 publications

Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

Systematic Review of Potential Anticancerous Activities of Erythrina senegalensis DC (Fabaceae)

Therapeutic Options for Chlamydia trachomatis Infection: Present and Future

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