Abstract:
:A novel series of homonucleosides and their double-headed analogs containing theophylline, 1,3,4-oxadiazole, and variant nucleobases was designed and synthesized. The new derivatives were fully characterized by HRMS, FT-IR, 1H NMR, and 13C NMR. The cytotoxic activities of all prepared compounds were screened in vitro against four cell lines, including fibrosarcoma (HT-1080), breast (MCF-7 and MDA-MB-231), and lung carcinoma (A-549). The double-headed analogue 18 showed marked growth inhibition against all the cell lines tested, specifically in HT-1080, with an IC50 values of 17.08 ± 0.97 µM. The possible mechanism of apoptosis was investigated using Annexin V staining, caspase-3/7 activity, and analysis cell cycle progression. The compound 18 induced apoptosis through caspase-3/7 activation and cell-cycle arrest in HT-1080 and A-549 cells. The molecular docking confirms that the compound 18 activated caspase-3 via the formation of hydrogen bonds and hydrophobic interactions.
journal_name
Bioorg Chemjournal_title
Bioorganic chemistryauthors
El Mansouri AE,Oubella A,Mehdi A,AitItto MY,Zahouily M,Morjani H,Lazrek HBdoi
10.1016/j.bioorg.2020.104558subject
Has Abstractpub_date
2020-12-15 00:00:00pages
104558eissn
0045-2068issn
1090-2120pii
S0045-2068(20)31856-3pub_type
杂志文章abstract::Five new maleimide derivatives, (+)- and (-)- farinomalein F (1), (+)- and (-)- farinomalein G (2), farinomalein H (3) and one new linearly fused prenylated indole alkaloid phomoamide (8), along with five known compounds 4-7 and 9 were isolated from the mangrove endophytic fungus Phomopsis sp. SYSUQYP-23. Their struct...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2020.103712
更新日期:2020-04-01 00:00:00
abstract::Some derivatives containing pyrido[2,3-d:6,5d']dipyrimidine-4,5-diones (9a-f), tetrahydropyrido[2,3-d]pyrimidine-6-carbonitriles (11a-c) and 6-(4-acetylphenyl)-2-thioxo-2,3,5,6,7,8-hexahydro-1H-pyrimido[4,5-d]pyrimidin-4-one (12) were synthesized from 6-amino-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (8). The anti-infla...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2018.01.028
更新日期:2018-04-01 00:00:00
abstract::The relationship between structure and activity of insect oostatic decapeptide (Aed-TMOF) analogues in flesh fly was analyzed. The highest oostatic activity was exhibited by the pentapetide and tetrapeptide analogues, H-Tyr-Asp-Pro-Ala-Pro-OH and H-Tyr-Asp-Pro-Ala-OH, respectively. The tetrapeptide, either native or t...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2004.05.003
更新日期:2004-08-01 00:00:00
abstract::Eight phenalenone derivatives, including four new compounds, aceneoherqueinones A and B (1 and 2), (+)-aceatrovenetinone A (3a), and (+)-aceatrovenetinone B (3d), along with four known congeners, (-)-aceatrovenetinone A (3b), (-)-aceatrovenetinone B (3c), (-)-scleroderolide (4a), and (+)-scleroderolide (4b), were char...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2020.104477
更新日期:2021-01-01 00:00:00
abstract::Activated carbon's porous structure allows it to adsorb a substrates, products and catalysts from the environment thus modificated the biocatalysis processes in digestive tract. Active carbons are currently used to remove solvents from gas streams and for water purification; however, few studies have examined the mech...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.02.029
更新日期:2019-12-01 00:00:00
abstract::A series of novel quinazolines as tubulin inhibitors occupying three zones of colchicine domain have been designed and synthesized inspired by the recently disclosed crystal structure of verubulin analogue 6 with tubulin. Among the newly synthesized compounds, 19c showed noteworthy potency against K562, HepG2, KB, HCT...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2018.10.027
更新日期:2019-03-01 00:00:00
abstract::Simple biomembrane models, namely micellar aggregates formed by enantiopure sodium N-acylprolinates, are able to convert the racemic mixture of bilirubin-IXalpha into an enantiomerically enriched mixture, thus suggesting a possible role of chirality in bilirubin toxicity due to the perturbation of neuron membrane dyna...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2008.05.001
更新日期:2008-10-01 00:00:00
abstract::The chemical investigation of the fruits of a mangrove Sonneratia apetala collected from the Beibu Gulf led to the isolation of four new compounds, sonneradons A-D (1-4), as well as 18 known compounds (5-22). The structures of the new compounds were elucidated based on extensive spectroscopic analysis, and the structu...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2020.103813
更新日期:2020-06-01 00:00:00
abstract::The DFT and HF calculation results for the proton transfer reactions of three different systems reveal that the reaction mechanism (transfer of a proton to a nucleophile) is largely determined by the distance between the two reactive centers (r). Systems with relatively large r values tend to abstract a proton from a ...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2009.04.003
更新日期:2009-08-01 00:00:00
abstract::In trying to develop new anticancer agents, a series of 1H-pyrazolo[3,4-b]pyridine derivatives was designed and synthesized. Fifteen compounds were evaluated in vitro for their anti-proliferative activity against HePG-2, MCF-7, HCT-116, and PC-3 cell lines. Additionally, DNA binding affinity of the synthesized derivat...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2016.05.006
更新日期:2016-08-01 00:00:00
abstract::A series of benzimidazole-oxindole conjugates were synthesized and evaluated for their cytotoxic activity. The cytotoxicity assay results suggest that conjugates 5c and 5p exhibit promising cytotoxicity against human breast cancer cell line (MCF-7). The Cell cycle analysis revealed that these conjugates induced cell c...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2015.09.003
更新日期:2015-12-01 00:00:00
abstract::3-Amino-1-aryl-1H-benzo[f]chromene-2-carbonitrile derivatives were synthesized from three-component reaction of arylaldehyde, malononitrile and 2-naphthol in the presence of 1, 4-bis(4-ferrocenylbutyl)piperazine as a new catalyst. Cytotoxic potencies of the compounds were tested on HT-29 cells. 3-Amino-1-(4-fluorophen...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.103329
更新日期:2019-12-01 00:00:00
abstract::Non-polio enteroviruses such as enterovirus A71 (EV-A71), EV-D68, and coxsackievirus B3 (CVB3) are significant human pathogens with disease manifestations ranging from mild flu-like symptoms to more severe encephalitis, myocarditis, acute flaccid paralysis/myelitis, and even death. There is currently no effective anti...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2020.103981
更新日期:2020-08-01 00:00:00
abstract::The competitive inhibition constants of series of inhibitors related to phenylacetic acid against both wild-type and the doubly mutanted C298A/W219Y aldose reductase have been measured. Van't Hoff analysis shows that these acids bind with an enthalpy near -6.8 kcal/mol derived from the electrostatic interactions, whil...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2006.09.004
更新日期:2006-12-01 00:00:00
abstract::A series of new cytisine derivatives with a unique endocyclic scaffold were synthesized and evaluated for their inhibitory effect on collagen α1 (I) (COL1A1) promotor in human LX2 cells, taking cytisine as the lead. Structure-activity relationship (SAR) revealed that introducing a 12N-benzyl substitution might signifi...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.103032
更新日期:2019-09-01 00:00:00
abstract::A facile synthetic strategy has been developed for the generation of structurally diverse N-fused heterocycles. The formation of fused 1,2,3-triazole indolo and pyrrolodiazepines proceeds through an initial Knoevenagel condensation followed by intramolecular azide-alkyne cycloaddition reaction at room temperature with...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.103306
更新日期:2019-12-01 00:00:00
abstract::Glycyrrhetinic acid has been usually studied for their anti-tumor activities. However, the low bioavailability and poor aqueous solubility as well as limited intracellular accumulation have limited their utility. In this present study, a series of new glycyrrhetinic acid conjugates with a triphenylphosphonium cation (...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2018.12.036
更新日期:2019-04-01 00:00:00
abstract::A series of novel pyrimidylaminoquinoline derivatives 8(a-i) and 9(a-i) containing amino side chain, and the bisaminoquinoline analogs 3(b-e) have been designed and synthesized by structural modifications on a lead DOT1L inhibitor, 3a. All the compounds have been evaluated for their DOT1L inhibitory activities. The re...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2018.07.022
更新日期:2018-10-01 00:00:00
abstract::A novel 1(2), 2(18)-diseco indole diterpenoid, drechmerin H (1), was isolated from the fermentation broth of Drechmeria sp. together with a new indole diterpenoid, 2'-epi terpendole A (3), and a known analogue, terpendole A (2). Their structures were determined by HRESIMS, 1D and 2D NMR, ECD, and X-ray single crystal ...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2018.05.001
更新日期:2018-09-01 00:00:00
abstract::Lysine specific demethylase 1 (LSD1) is a flavin-dependent amine oxidase that selectively removes one or two methyl groups from H3 at Lys4 and is recognized as a promising therapeutic target for cancer and other diseases. Here, a series of 3-oxoamino-benzenesulfonamides were synthesized and evaluated for their inhibit...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2017.04.006
更新日期:2017-06-01 00:00:00
abstract::A novel series of tacrine derivatives containing sulfonamide group were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. The result showed that all the synthesized tacrine-sulfonamides (VIIIa-o) exhibited inhibitory activity on both cholinesteras...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2017.01.005
更新日期:2017-02-01 00:00:00
abstract::In the present work, a novel series of B-RAF kinase inhibitors having imidazo[2,1-b]oxazole scaffold was designed and synthesized based on the structures of the well-known B-RAF inhibitors. The twenty two final compounds were tested over A375 and SKMEL28 cell lines to determine the primary cytotoxic activity of these ...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.103349
更新日期:2019-12-01 00:00:00
abstract::The structurally related tetrapyrrolic pigments are a group of natural products that participate in many of the fundamental biosynthetic and catabolic processes of living organisms. Porphobilinogen synthase catalyzes a rate-limiting step for the biosyntheses of tetrapyrrolic natural products. In the present study, a v...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2008.11.001
更新日期:2009-02-01 00:00:00
abstract::For the first time, the structure-activity relationships of thirteen synthesized flavonoids have been investigated by evaluating their ability to modulate horseradish peroxidase (HRP) catalytic activity. Indeed, a modified spectrophotometrically method was carried out and optimized using 4-methylcatechol (4-MC) as per...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2017.08.001
更新日期:2017-10-01 00:00:00
abstract::Breaking a carbon-hydrogen bond adjacent to a carbonyl is a slow step in a large number of chemical reactions. However, many enzymes are capable of catalyzing this reaction with great efficiency. One of the most proficient of these enzymes is 3-oxo-Delta5-steroid isomerase (KSI), which catalyzes the isomerization of a...
journal_title:Bioorganic chemistry
pub_type: 杂志文章,评审
doi:10.1016/j.bioorg.2004.06.005
更新日期:2004-10-01 00:00:00
abstract::The non-mevalonate or 2-C-methyl-d-erythritol-4-phosphate (MEP) pathway is responsible for generating isoprenoid precursors in plants, protozoa, and bacteria. Because this pathway is absent in humans, its enzymes represent potential targets for the development of herbicides and antibiotics. 1-Deoxy-d-xylulose (DXP) re...
journal_title:Bioorganic chemistry
pub_type: 杂志文章,评审
doi:10.1016/j.bioorg.2014.06.001
更新日期:2014-12-01 00:00:00
abstract::Three different modified phosphoramidite nucleoside building blocks equipped with additional protected imidazole, masked alcohol and masked carboxylate functionality are synthesized and incorporated into oligonucleotides. Based on the serine-protease active site model, doubly and triply modified duplexes are created a...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2010.01.002
更新日期:2010-06-01 00:00:00
abstract::The Forkhead boX M1 (FOXM1) protein is an essential transcription factor required for the normal activation of human cell cycle. However, increasing evidence supports a correlation between FOXM1 overexpression and the onset of several types of cancer. Based on a previously reported molecular modeling and molecular dyn...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.103269
更新日期:2019-12-01 00:00:00
abstract::The current study is concerned with the identification of lead molecules based on the bis-coumarin scaffold having selective urease inhibitory and antiglycation activities. For that purpose, bis-coumarins (1-44) were synthesized and structurally characterized by different spectroscopic techniques. Eight derivatives 4,...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.103170
更新日期:2019-10-01 00:00:00
abstract::With the rapid development of nanotechnology, much has been anticipated with silver nanoparticles (AgNPs) due to their extensive industrial and commercial applications. However, it has raised concerns over environmental safety and human health effects. In this study, AgNPs were bio-fabricated using aqueous extract of ...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2020.104535
更新日期:2020-12-11 00:00:00