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Article ; Online: 11 H -Indeno[1,2- b ]quinoxalin-11-one 2-(4-ethylbenzylidene)hydrazone

Anastasia R. Kovrizhina / Elizaveta I. Samorodova / Andrei I. Khlebnikov

Molbank, Vol 2021, Iss M1299, p M

2021 Volume 1299

Abstract: 11 H -Indeno[1,2- b ]quinoxaline derivatives present an important type of nitrogen-containing heterocyclic compound that are useful intermediate products in organic synthesis and have potential pharmaceutical applications. A new 11 H -indeno[1,2- b ] ... ...

Abstract	11 H -Indeno[1,2- b ]quinoxaline derivatives present an important type of nitrogen-containing heterocyclic compound that are useful intermediate products in organic synthesis and have potential pharmaceutical applications. A new 11 H -indeno[1,2- b ]quinoxalin-11-one-2-(4-ethylbenzylidene)hydrazone (compound 3 ) was synthesized. Compound 3 is the first example of an azine derivative based on the 11 H -indeno[1,2- b ]quinoxaline system. The Z , E -isomerism of compound 3 was investigated by DFT calculations. Bioavailability was evaluated in silico using ADME predictions. According to the ADME results, compound 3 is potentially highly bioavailable and has potential to be used for the treatment of neuroinflammation and ischemia–reperfusion injury.
Keywords	azine ; aldazine ; 11 H -indeno[1,2- b ]quinoxalin-11-one ; DFT ; ADME ; Inorganic chemistry ; QD146-197
Subject code	540
Language	English
Publishing date	2021-11-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: 2-(2-(Fluorosulfonyloxy)phenyl)benzoxazole

Nadezhda V. Danilenko / Vladimir I. Shmalyuk / Andrei I. Khlebnikov

Molbank, Vol 2021, Iss M1242, p M

2021 Volume 1242

Abstract: The fluorosulfate derivatives of benzoxazole attract attention since benzoxazole-based compounds have a wide range of biological activities, and the ability of the –SO 2 F group to react with various functional groups makes it possible to synthesize ... ...

Abstract	The fluorosulfate derivatives of benzoxazole attract attention since benzoxazole-based compounds have a wide range of biological activities, and the ability of the –SO 2 F group to react with various functional groups makes it possible to synthesize various new derivatives. The new 2-(2-(fluorosulfonyloxy)phenyl)benzoxazole ( 2 ) has been synthesized by the SuFEx click reaction in a two-chamber reactor. Compound 2 is the first example of a benzoxazole derivative with a fluorosulfate-containing substituent at position two of the benzoxazole heterocycle. The anti-cancer potency of 2 was evaluated in silico using molecular docking. The docking results suggest that title compound 2 is of great interest for further studies as a possible anaplastic lymphoma kinase inhibitor.
Keywords	benzoxazole ; SuFEx ; molecular docking ; Inorganic chemistry ; QD146-197
Language	English
Publishing date	2021-07-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: 2-(4-(Fluorosulfonyloxy)phenyl)benzoxazole

Nadezhda V. Danilenko / Mariia O. Lutsuk / Svetlana E. Patlasova / Elena I. Korotkova / Andrei I. Khlebnikov

Molbank, Vol 2023, Iss 4, p M

2023 Volume 1746

Abstract: New 2-(4-(fluorosulfonyloxy)phenyl)benzoxazole ( 2 ) was synthesized through the SuFEx click reaction in a two-chamber reactor. The effect of silylation on the yield of the target compound was investigated. The fluorescent properties of compound 2 were ... ...

Abstract	New 2-(4-(fluorosulfonyloxy)phenyl)benzoxazole ( 2 ) was synthesized through the SuFEx click reaction in a two-chamber reactor. The effect of silylation on the yield of the target compound was investigated. The fluorescent properties of compound 2 were determined using experimental and computational methods.
Keywords	benzoxazole ; SuFEx ; fluorescent properties ; Inorganic chemistry ; QD146-197
Language	English
Publishing date	2023-11-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Peptide Blocking CTLA-4 and B7-1 Interaction

Stepan V. Podlesnykh / Kristina E. Abramova / Anastasia Gordeeva / Andrei I. Khlebnikov / Andrei I. Chapoval

Molecules, Vol 26, Iss 2, p

2021 Volume 253

Abstract: Discovery of the B7 family immune checkpoints such as CTLA-4 (CD152), PD-1 (CD279), as well as their ligands B7-1 (CD80), B7-2 (CD86), B7-H1 (PD-L1, CD274), and B7-DC (PD-L2, CD273), has opened new possibilities for cancer immunotherapy using monoclonal ... ...

Abstract	Discovery of the B7 family immune checkpoints such as CTLA-4 (CD152), PD-1 (CD279), as well as their ligands B7-1 (CD80), B7-2 (CD86), B7-H1 (PD-L1, CD274), and B7-DC (PD-L2, CD273), has opened new possibilities for cancer immunotherapy using monoclonal antibodies (mAb). The blockade of inhibitory receptors (CTLA-4 and PD-1) with specific mAb results in the activation of cancer patients’ T lymphocytes and tumor rejection. However, the use of mAb in clinics has several limitations including side effects and cost of treatment. The development of new low-molecular compounds that block immune checkpoints’ functional activity can help to overcome some of these limitations. In this paper, we describe a synthetic peptide (p344) containing 14 amino acids that specifically interact with CTLA-4 protein. A 3D computer model suggests that this peptide binds to the 99 MYPPPY 104 loop of CTLA-4 protein and potentially blocks the contact of CTLA-4 receptor with B7-1 ligand. Experimental data confirm the peptide-specific interaction with CTLA-4 and its ability to partially block CTLA-4/B7-1 binding. The identified synthetic peptide can be used for the development of novel immune checkpoint inhibitors that can block CTLA-4 functional activity for cancer immunotherapy.
Keywords	peptides ; immune checkpoints ; peptide microarray ; cancer ; immunotherapy ; Organic chemistry ; QD241-441
Subject code	616
Language	English
Publishing date	2021-01-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Neutrophil Immunomodulatory Activity of Farnesene, a Component of Artemisia dracunculus Essential Oils

Igor A. Schepetkin / Gulmira Özek / Temel Özek / Liliya N. Kirpotina / Andrei I. Khlebnikov / Robyn A. Klein / Mark T. Quinn

Pharmaceuticals, Vol 15, Iss 642, p

2022 Volume 642

Abstract: Despite their reported therapeutic properties, not much is known about the immunomodulatory activity of essential oils present in Artemisia species. We isolated essential oils from the flowers and leaves of five Artemisia species: A. tridentata , A. ... ...

Abstract	Despite their reported therapeutic properties, not much is known about the immunomodulatory activity of essential oils present in Artemisia species. We isolated essential oils from the flowers and leaves of five Artemisia species: A. tridentata , A. ludoviciana , A. dracunculus , A. frigida , and A. cana . The chemical composition of the Artemisia essential oil samples had similarities and differences as compared to those previously reported in the literature. The main components of essential oils obtained from A. tridentata , A. ludoviciana , A. frigida , and A. cana were camphor (23.0–51.3%), 1,8-cineole (5.7–30.0%), camphene (1.6–7.7%), borneol (2.3–14.6%), artemisiole (1.2–7.5%), terpinen-4-ol (2.0–6.9%), α-pinene (0.8–3.9%), and santolinatriene (0.7–3.5%). Essential oils from A. dracunculus were enriched in methyl chavicol (38.8–42.9%), methyl eugenol (26.1–26.4%), terpinolene (5.5–8.8%), ( E / Z )-β-ocimene (7.3–16.0%), β-phellandrene (1.3–2.2%), p -cymen-8-ol (0.9–2.3%), and xanthoxylin (1.2–2.2%). A comparison across species also demonstrated that some compounds were present in only one Artemisia species. Although Artemisia essential oils were weak activators of human neutrophils, they were relatively more potent in inhibiting subsequent neutrophil Ca 2+ mobilization with N -formyl peptide receptor 1 (FPR1) agonist f MLF- and FPR2 agonist WKYMVM, with the most potent being essential oils from A. dracunculus . Further analysis of unique compounds found in A. dracunculus showed that farnesene, a compound with a similar hydrocarbon structure as lipoxin A 4 , inhibited Ca 2+ influx induced in human neutrophils by f MLF (IC 50 = 1.2 μM), WKYMVM (IC 50 = 1.4 μM), or interleukin 8 (IC 50 = 2.6 μM). Pretreatment with A. dracunculus essential oils and farnesene also inhibited human neutrophil chemotaxis induced by f MLF, suggesting these treatments down-regulated human neutrophil responses to inflammatory chemoattractants. Thus, our studies have identified farnesene as a potential anti-inflammatory modulator of ...
Keywords	anti-inflammatory ; Artemisia ; calcium flux ; chemotaxis ; essential oils ; farnesene ; Medicine ; R ; Pharmacy and materia medica ; RS1-441
Subject code	571
Language	English
Publishing date	2022-05-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Neutrophil Immunomodulatory Activity of (−)-Borneol, a Major Component of Essential Oils Extracted from Grindelia squarrosa

Igor A. Schepetkin / Gulmira Özek / Temel Özek / Liliya N. Kirpotina / Andrei I. Khlebnikov / Mark T. Quinn

Molecules, Vol 27, Iss 4897, p

2022 Volume 4897

Abstract: Grindelia squarrosa (Pursh) Dunal is used in traditional medicine for treating various diseases; however, little is known about the immunomodulatory activity of essential oils from this plant. Thus, we isolated essential oils from the flowers (GEO Fl ) ... ...

Abstract	Grindelia squarrosa (Pursh) Dunal is used in traditional medicine for treating various diseases; however, little is known about the immunomodulatory activity of essential oils from this plant. Thus, we isolated essential oils from the flowers (GEO Fl ) and leaves (GEO Lv ) of G. squarrosa and evaluated the chemical composition and innate immunomodulatory activity of these essential oils. Compositional analysis of these essential oils revealed that the main components were α-pinene (24.7 and 23.2% in GEO Fl and GEO Lv , respectively), limonene (10.0 and 14.7%), borneol (23.4 and 16.6%), p -cymen-8-ol (6.1 and 5.8%), β-pinene (4.0 and 3.8%), bornyl acetate (3.0 and 5.1%), trans -pinocarveol (4.2 and 3.7%), spathulenol (3.0 and 2.0%), myrtenol (2.5 and 1.7%), and terpinolene (1.7 and 2.0%). Enantiomer analysis showed that α-pinene, β-pinene, and borneol were present primarily as (−)-enantiomers (100% enantiomeric excess (ee) for (−)-α-pinene and (−)-borneol in both GEO Fl and GEO Lv 82 and 78% ee for (−)-β-pinene in GEO Fl and GEO Lv ), while limonene was present primarily as the (+)-enantiomer (94 and 96 ee in GEO Fl and GEO Lv ). Grindelia essential oils activated human neutrophils, resulting in increased [Ca 2+ ] i (EC 50 = 22.3 µg/mL for GEO Fl and 19.4 µg/mL for GEO Lv ). In addition, one of the major enantiomeric components, (−)-borneol, activated human neutrophil [Ca 2+ ] i (EC 50 = 28.7 ± 2.6), whereas (+)-borneol was inactive. Since these treatments activated neutrophils, we also evaluated if they were able to down-regulate neutrophil responses to subsequent agonist activation and found that treatment with Grindelia essential oils inhibited activation of these cells by the N -formyl peptide receptor 1 (FPR1) agonist f MLF and the FPR2 agonist WKYMVM. Likewise, (−)-borneol inhibited FPR-agonist-induced Ca 2+ influx in neutrophils. Grindelia leaf and flower essential oils, as well as (−)-borneol, also inhibited f MLF-induced chemotaxis of human neutrophils (IC 50 = 4.1 ± 0.8 µg/mL, 5.0 ± 1.6 µg/mL, and 5.8 ...
Keywords	borneol ; calcium influx ; chemotaxis ; essential oils ; Grindelia squarrosa ; monoterpene ; Organic chemistry ; QD241-441
Subject code	290
Language	English
Publishing date	2022-07-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Volatile Composition, Antimicrobial Activity, and In Vitro Innate Immunomodulatory Activity of Echinacea purpurea (L.) Moench Essential Oils

Noura S. Dosoky / Liliya N. Kirpotina / Igor A. Schepetkin / Andrei I. Khlebnikov / Brent L. Lisonbee / Jeffrey L. Black / Hillary Woolf / Trever L. Thurgood / Brittany L. Graf / Prabodh Satyal / Mark T. Quinn

Molecules, Vol 28, Iss 21, p

2023 Volume 7330

Abstract: Echinacea purpurea (L.) Moench is a medicinal plant commonly used for the treatment of upper respiratory tract infections, the common cold, sore throat, migraine, colic, stomach cramps, and toothaches and the promotion of wound healing. Based on the ... ...

Abstract	Echinacea purpurea (L.) Moench is a medicinal plant commonly used for the treatment of upper respiratory tract infections, the common cold, sore throat, migraine, colic, stomach cramps, and toothaches and the promotion of wound healing. Based on the known pharmacological properties of essential oils (EOs), we hypothesized that E. purpurea EOs may contribute to these medicinal properties. In this work, EOs from the flowers of E. purpurea were steam-distilled and analyzed by gas chromatography–mass spectrometry (GC–MS), GC with flame-ionization detection (GC–FID), and chiral GC–MS. The EOs were also evaluated for in vitro antimicrobial and innate immunomodulatory activity. About 87 compounds were identified in five samples of the steam-distilled E. purpurea EO. The major components of the E. purpurea EO were germacrene D (42.0 ± 4.61%), α-phellandrene (10.09 ± 1.59%), β-caryophyllene (5.75 ± 1.72%), γ-curcumene (5.03 ± 1.96%), α-pinene (4.44 ± 1.78%), δ-cadinene (3.31 ± 0.61%), and β-pinene (2.43 ± 0.98%). Eleven chiral compounds were identified in the E. purpurea EO, including α-pinene, sabinene, β-pinene, α-phellandrene, limonene, β-phellandrene, α-copaene, β-elemene, β-caryophyllene, germacrene D, and δ-cadinene. Analysis of E. purpurea EO antimicrobial activity showed that they inhibited the growth of several bacterial species, although the EO did not seem to be effective for Staphylococcus aureus . The E. purpurea EO and its major components induced intracellular calcium mobilization in human neutrophils. Additionally, pretreatment of human neutrophils with the E. purpurea EO or (+)-δ-cadinene suppressed agonist-induced neutrophil calcium mobilization and chemotaxis. Moreover, pharmacophore mapping studies predicted two potential MAPK targets for (+)-δ-cadinene. Our results are consistent with previous reports on the innate immunomodulatory activities of β-caryophyllene, α-phellandrene, and germacrene D. Thus, this study identified δ-cadinene as a novel neutrophil agonist and suggests that δ-cadinene may ...
Keywords	Echinacea purpurea ; purple coneflower ; essential oil ; antimicrobial activity ; (+)-δ-cadinene ; calcium flux ; Organic chemistry ; QD241-441
Subject code	571
Language	English
Publishing date	2023-10-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Absorption of Water Vapor by Bambus[6]uril and a Density Functional Theory Study of Its Aqua Complexes

Pana Turebayeva / Alexey N. Guslyakov / Svetlana A. Novikova / Andrei I. Khlebnikov / Ekaterina A. Befus / Evgeniy P. Meshcheryakov / Abdigali A. Bakibaev / Lyazat Kusepova / Nazira Kassenova / Sarzhan Sharipova / Rakhmetulla Yerkassov

Molecules, Vol 28, Iss 23, p

2023 Volume 7680

Abstract: The absorption/desorption of water vapor by bambus[6]uril (Bu[6]) has been studied. According to kinetic experiments, the absorption capacity of Bu[6] is 4 moles of water per 1 mole of Bu[6] with the absorption duration of 20 min and the complete ... ...

Abstract	The absorption/desorption of water vapor by bambus[6]uril (Bu[6]) has been studied. According to kinetic experiments, the absorption capacity of Bu[6] is 4 moles of water per 1 mole of Bu[6] with the absorption duration of 20 min and the complete desorption duration of 100 min. Experimental rate constants for water vapor absorption and desorption by Bu[6] have been determined to be 0.166 min −1 and 0.0221 min −1 , respectively. The obtained results are in agreement with theoretical calculations using the DFT method. A hypothetical structure of bambus[6]uril tetrahydrate (Bu[6]·4H 2 O) has been proposed based on the experimental and DFT data.
Keywords	bambus[6]uril ; water absorption ; DFT calculations ; water desorption ; aqua complex ; Organic chemistry ; QD241-441
Language	English
Publishing date	2023-11-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Novel Tryptanthrin Derivatives with Selectivity as c –Jun N–Terminal Kinase (JNK) 3 Inhibitors

Igor A. Schepetkin / Oleksander S. Karpenko / Anastasia R. Kovrizhina / Liliya N. Kirpotina / Andrei I. Khlebnikov / Stepan I. Chekal / Alevtyna V. Radudik / Maryna O. Shybinska / Mark T. Quinn

Molecules, Vol 28, Iss 4806, p

2023 Volume 4806

Abstract: The c -Jun N-terminal kinase (JNK) family includes three proteins (JNK1-3) that regulate many physiological processes, including cell proliferation and differentiation, cell survival, and inflammation. Because of emerging data suggesting that JNK3 may ... ...

Abstract	The c -Jun N-terminal kinase (JNK) family includes three proteins (JNK1-3) that regulate many physiological processes, including cell proliferation and differentiation, cell survival, and inflammation. Because of emerging data suggesting that JNK3 may play an important role in neurodegenerative diseases, such as Alzheimer’s disease (AD) and Parkinson’s disease, as well as cancer pathogenesis, we sought to identify JNK inhibitors with increased selectivity for JNK3. A panel of 26 novel tryptanthrin-6-oxime analogs was synthesized and evaluated for JNK1-3 binding (K d ) and inhibition of cellular inflammatory responses. Compounds 4d (8-methoxyindolo[2,1- b ]quinazolin-6,12-dione oxime) and 4e (8-phenylindolo[2,1- b ]quinazolin-6,12-dione oxime) had high selectivity for JNK3 versus JNK1 and JNK2 and inhibited lipopolysaccharide (LPS)-induced nuclear factor-κB/activating protein 1 (NF-κB/AP-1) transcriptional activity in THP-1Blue cells and interleukin-6 (IL-6) production by MonoMac-6 monocytic cells in the low micromolar range. Likewise, compounds 4d , 4e , and pan-JNK inhibitor 4h (9-methylindolo[2,1- b ]quinazolin-6,12-dione oxime) decreased LPS-induced c -Jun phosphorylation in MonoMac-6 cells, directly confirming JNK inhibition. Molecular modeling suggested modes of binding interaction of these compounds in the JNK3 catalytic site that were in agreement with the experimental data on JNK3 binding. Our results demonstrate the potential for developing anti-inflammatory drugs based on these nitrogen-containing heterocyclic systems with selectivity for JNK3.
Keywords	anti-inflammatory ; c -Jun N-terminal kinase ; molecular docking ; nuclear factor-κB ; oxime ; selective kinase inhibitor ; Organic chemistry ; QD241-441
Subject code	540
Language	English
Publishing date	2023-06-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Chemical Composition and Immunomodulatory Activity of Essential Oils from Rhododendron albiflorum

Igor A. Schepetkin / Gulmira Özek / Temel Özek / Liliya N. Kirpotina / Andrei I. Khlebnikov / Mark T. Quinn

Molecules, Vol 26, Iss 3652, p

2021 Volume 3652

Abstract: Rhododendron (Ericaceae) extracts contain flavonoids, chromones, terpenoids, steroids, and essential oils and are used in traditional ethnobotanical medicine. However, little is known about the immunomodulatory activity of essential oils isolated from ... ...

Abstract	Rhododendron (Ericaceae) extracts contain flavonoids, chromones, terpenoids, steroids, and essential oils and are used in traditional ethnobotanical medicine. However, little is known about the immunomodulatory activity of essential oils isolated from these plants. Thus, we isolated essential oils from the flowers and leaves of R. albiflorum (cascade azalea) and analyzed their chemical composition and innate immunomodulatory activity. Compositional analysis of flower (REO Fl ) versus leaf (REO Lv ) essential oils revealed significant differences. REO Fl was comprised mainly of monoterpenes (92%), whereas sesquiterpenes were found in relatively low amounts. In contrast, REO Lv was primarily composed of sesquiterpenes (90.9%), with a small number of monoterpenes. REO Lv and its primary sesquiterpenes (viridiflorol, spathulenol, curzerene, and germacrone) induced intracellular Ca 2+ mobilization in human neutrophils, C20 microglial cells, and HL60 cells transfected with N -formyl peptide receptor 1 (FPR1) or FPR2. On the other hand, pretreatment with these essential oils or component compounds inhibited agonist-induced Ca 2+ mobilization and chemotaxis in human neutrophils and agonist-induced Ca 2+ mobilization in microglial cells and FPR-transfected HL60 cells, indicating that the direct effect of these compounds on [Ca 2+ ] i desensitized the cells to subsequent agonist activation. Reverse pharmacophore mapping suggested several potential kinase targets for these compounds; however, these targets were not supported by kinase binding assays. Our results provide a cellular and molecular basis to explain at least part of the beneficial immunotherapeutic properties of the R. albiflorum essential oils and suggest that essential oils from leaves of this plant may be effective in modulating some innate immune responses, possibly by inhibition of neutrophil migration.
Keywords	Rhododendron albiflorum ; essential oil ; calcium flux ; neutrophil ; chemotaxis ; sesquiterpene ; Organic chemistry ; QD241-441
Subject code	571
Language	English
Publishing date	2021-06-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
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