Synthesis, Molecular Docking, Molecular Dynamics Studies, and In Vitro Biological Evaluation of New Biofunctional Ketoprofen Derivatives with Different N-Containing Heterocycles

Manolov, Stanimir; Bojilov, Dimitar; Ivanov, Iliyan; Marc, Gabriel; Bataklieva, Nadezhda; Oniga, Smaranda; Oniga, Ovidiu; Nedialkov, Paraskev

doi:10.3390/pr11061837

Cited by 4 publications

(3 citation statements)

References 47 publications

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“…Nonsteroidal and steroidal anti-inflammatory drugs reduce inflammation, but these drugs have many unwanted side effects. Anti-inflammatory drugs are known to show a dose-dependent ability to inhibit thermally induced protein denaturation [68,69]. The results showed that the leaf extracts had better anti-inflammatory activity than the fruit extracts.…”

Section: Discussionmentioning

confidence: 99%

Metabolic Profile of Leaves and Pulp of Passiflora caerulea L. (Bulgaria) and Their Biological Activities

Gerasimova,

Nikolova,

Petkova

et al. 2024

Plants

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At present, there are no data in the scientific literature on studies aimed at characterizing Passiflora caerulea L. growing in Bulgaria. The present study aimed to investigate the metabolic profile and elemental composition of the leaves and pulp of this Passiflora, as well as to evaluate the antioxidant, antimicrobial and anti-inflammatory activities of its leaf and pulp extracts. The results showed that the pulp predominantly contained the essential amino acid histidine (7.81 mg g−1), while it was absent in the leaves, with the highest concentration being tryptophan (8.30 mg g−1). Of the fatty acids, palmitoleic acid predominated both in the pulp and in the leaves. A major sterol component was β-sitosterol. Fructose (7.50%) was the predominant sugar in the pulp, while for the leaves, it was glucose—1.51%. Seven elements were identified: sodium, potassium, iron, magnesium, manganese, copper and zinc. The highest concentrations of K and Mg were in the pulp (23,946 mg kg−1 and 1890 mg kg−1) and leaves (36,179 mg kg−1 and 5064 mg kg−1). According to the DPPH, FRAP and CUPRAC methods, the highest values for antioxidant activity were found in 70% ethanolic extracts of the leaves, while for the ABTS method, the highest value was found in 50% ethanolic extracts. In the pulp, for all four methods, the highest values were determined at 50% ethanolic extracts. Regarding the antibacterial activity, the 50% ethanolic leaf extracts were more effective against the Gram-positive bacteria. At the same time, the 70% ethanolic leaf extract was more effective against Gram-negative bacteria such as Salmonella enteritidis ATCC 13076. The leaf extracts exhibited higher anti-inflammatory activity than the extracts prepared from the pulp. The obtained results revealed that P. caerulea is a plant that can be successfully applied as an active ingredient in various nutritional supplements or cosmetic products.

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Section: Discussionmentioning

confidence: 99%

Metabolic Profile of Leaves and Pulp of Passiflora caerulea L. (Bulgaria) and Their Biological Activities

Gerasimova,

Nikolova,

Petkova

et al. 2024

Plants

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“…The affinity of arzanol, (R)-bitalin A, and (S)-bitalin A to the human serum albumin was evaluated according to the previously reported protocol in a molecular docking study [67]. The stability of the predicted complexes between human serum albumin and the three compounds was evaluated further using a molecular dynamics study, according to the previously reported protocol [67,68].…”

Section: %I Ad =mentioning

confidence: 99%

HPLC Analysis and In Vitro and In Silico Evaluation of the Biological Activity of Polyphenolic Components Separated with Solvents of Various Polarities from Helichrysum italicum

Bojilov,

Manolov,

Ahmed

et al. 2023

Molecules

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Helichrysum italicum has piqued the interest of many researchers in recent years, mostly for its essential oil, but increasingly for its polyphenolic content as well. In the current study, we examine the polyphenolic composition of H. italicum grown in Bulgaria. The polyphenolic complex was fractionated with solvents of various polarities, including hexane, chloroform, ethyl acetate, and butanol, in order to assess the biological impact of the components. HPLC-PDA and UHPLC-MS/MS were used to examine all fractions. The green coffee fingerprint profile was employed as a “surrogate standard” in the polyphenolic components detection approach. From the UHPLC-MS/MS analysis, we identified 60 components of the polyphenolic complex such as quercetin 3-O-glucuronide, quercetin acetyl-glycoside, isorhamnetin acetyl-glycoside, isorhamnetin caffeoyl-glycoside, quercetin caffeoyl-malonyl-glycoside, isorhamnetin coumaroyl-glycoside, coumaroyl-caffeoylquinic acid, and diCQA-acetyl-derivative were first reported in the composition of H. italicum. The biological activity of the fractions was evaluated in vitro and in silico, which included the fight against oxidative stress (hydrogen peroxide scavenging activity (HPSA), hydroxyl radical scavenging activity (HRSA), metal-chelating activity (MChA)) and nitrosative (nitric oxide scavenging activity) (NOSA)), in vitro anti-inflammatory, and anti-arthritic activity. Results are presented as IC50 ± SD μg/mL. The analysis showed that the EtOAc fraction was characterized by highest HPSA (57.12 ± 1.14 μg/mL), HRSA (92.23 ± 1.10 μg/mL), MChA (5.60 ± 0.17 μg/mL), and NOSA (89.81 ± 2.09 μg/mL), while the hexane and chloroform fractions showed significantly higher in vitro anti-inflammatory activity (30.48 ± 2.33 μg/mL, 62.50 ± 1.69 μg/mL) compared to the standard ibuprofen. All three fractions showed potential anti-arthritic activity (102.93 ± 8.62 μg/mL, 108.92 ± 4.42 μg/mL, 84.19 ± 3.89 μg/mL).

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“…The findings regarding the antibacterial activity, antioxidant effect, and toxicity experiments, as well as in silico analysis, demonstrated the potential of N-{4-[(4-bromophenyl)sulfonyl]benzoyl}-L-valine and 2-{4-[(4-bromophenyl)sulfonyl]phenyl}-4-isopropyl-4H-1,3-oxazol-5-one for the development of new antimicrobial drugs to combat Gram-positive bacteria, particularly Enterococcus faecium biofilm-associated illnesses. Manolov and co-workers [4] reported the synthesis of a series of novel compounds between ketoprofen and nitrogen-containing heterocyclic compounds (piperidine, pyrrolidine, 1,2,3,4-tetrahydroquinoline, and 1,2,3,4-tetrahydroisoquinoline). The compounds were investigated for their anti-inflammatory and antioxidant properties in vitro.…”

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confidence: 99%

Special Issue: Synthesis, Application, and Biological Evaluation of Chemical Organic Compounds

Manolov,

Ivanov

2023

Processes

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Synthesis, Molecular Docking, Molecular Dynamics Studies, and In Vitro Biological Evaluation of New Biofunctional Ketoprofen Derivatives with Different N-Containing Heterocycles

Cited by 4 publications

References 47 publications

Metabolic Profile of Leaves and Pulp of Passiflora caerulea L. (Bulgaria) and Their Biological Activities

Metabolic Profile of Leaves and Pulp of Passiflora caerulea L. (Bulgaria) and Their Biological Activities

HPLC Analysis and In Vitro and In Silico Evaluation of the Biological Activity of Polyphenolic Components Separated with Solvents of Various Polarities from Helichrysum italicum

Special Issue: Synthesis, Application, and Biological Evaluation of Chemical Organic Compounds

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