Abstract:
:Thirteen cationic peptidomimetics derived from amino acids bearing an alkyl or ethynylphenyl moiety that mimic the structure of cationic antibacterial peptides were designed and synthesized using a simple coupling reaction of an amino acid with a substituted amine. Antibacterial activities of the resulting peptidomimetics against drug-sensitive bacteria, such as Gram-positive Staphylococcus aureus (S. aureus) and Bacillus subtilis, Gram-negative Escherichia coli (E. coli) and Salmonella enterica, and a drug-resistant bacterium, methicillin-resistant S. aureus (MRSA), were systematically evaluated. Most peptidomimetics show significant broad-spectrum antibacterial activity. A-L-Iso-C12 (isoleucine derivative bearing a dodecyl moiety) show MICs of 2.5 μg/mL against S. aureus and 4 μg/mL against MRSA and A-L-Val-C12 (valine derivative bearing a dodecyl moiety) show MICs of 1.67 μg/mL against E. coli and 8.3 μg/mL against MRSA. A-L-Val-C12 showed low cytotoxicity toward L929 cells in comparison with SGC 7901 cells, indicating tumor-directed killing by peptidomimetics while avoiding toxicity to normal cells. The influences of type of amino acid and substituent, length of substituent, and stereochemistry of amino acids on antibacterial activity and cytotoxicity of peptidomimetics were systematically investigated. The results indicate that this series of cationic peptidomimetics derived from amino acids display antitumor activity and may be useful for treatment of bacterial infections.
journal_name
Bioorg Chemjournal_title
Bioorganic chemistryauthors
Li H,Fu S,Wang Y,Yuan X,Liu L,Dong H,Wang Q,Zhang Zdoi
10.1016/j.bioorg.2020.104506subject
Has Abstractpub_date
2021-01-01 00:00:00pages
104506eissn
0045-2068issn
1090-2120pii
S0045-2068(20)31804-6journal_volume
106pub_type
杂志文章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::Herein, we synthesized a series of twelve benzoxazole and benzothiazole derivatives incorporated with phthalimide core as anticancer agents. The most active compounds were 5a and 5g against HepG2 and MCF7 cell lines with IC50 = 0.011 and 0.006 μM, respectively. They evaluated against EGFR and HER2 enzymes. From cell c...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.102978
更新日期:2019-08-01 00:00:00
abstract::A new series of s-triazine derivatives incorporating sulfanilamide, homosulfanilamide, 4-aminoethyl-benzenesulfonamide and piperazine or aminoalcohol structural motifs is reported. Molecular docking was exploited to select compounds from virtual combinatorial library for synthesis and subsequent biological evaluation....
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2017.12.034
更新日期:2018-04-01 00:00:00
abstract::Two β-secreatase (BACE1) inhibitors from natural products (cinnamic acid and flavone) were linked to furnish potent, cell permeable BACE1 inhibitors with noncompetitive mode of inhibition, with the assistance of saturated transfer difference (STD)-NMR technique. Some of these conjugates also exhibited selective BACE1 ...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.103253
更新日期:2019-11-01 00:00:00
abstract::The coenzyme function of ubiquinone was subject of extensive studies in mitochondria since more than 40 years. The catalytic activity of ubiquinone (UQ) in electron transfer and proton translocation in cooperation with mitochondrial dehydrogenases and cytochromes contributes essentially to the bioenergetic activity of...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1006/bioo.2000.1193
更新日期:2001-02-01 00:00:00
abstract::The stereoselective synthesis and anti- Hymenolepis nana activity of six Linezolid-type compounds, obtained by chemical modification of l-Alanine, are reported in this work. The synthetic strategy was to prepare diasteromeric N,N-dibenzylamino oxazolidinones 1 and 2, and coupling with 4-(4-bromophenyl)morpholine (3) t...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2020.104359
更新日期:2020-12-01 00:00:00
abstract::Seven new taxane diterpenoids taxumarienes A-G (1-7) were isolated from the leaves of Taxus mairei, along with seven known analogous (8-14). The structures of the new compounds were elucidated based on the analysis of NMR and MS spectroscopy. All isolates were evaluated for their α-glucosidase inhibitory activities. A...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.103400
更新日期:2020-01-01 00:00:00
abstract::Alzheimer's Disease (AD) is a progressive neurodegenerative disorder that effects 50 million people worldwide. In this review, AD pathology and the development of novel therapeutic agents targeting AD were fully discussed. In particular, common approaches to prevent Aβ production and/or accumulation in the brain inclu...
journal_title:Bioorganic chemistry
pub_type: 杂志文章,评审
doi:10.1016/j.bioorg.2020.103649
更新日期:2020-04-01 00:00:00
abstract::The isomerization of l-amino acids in peptides and proteins into d-configuration under physiological conditions would affect the physiological dysfunction and caused protein conformational diseases. The presence of d-amino acids might change the higher-order structure of proteins and triggered abnormal aggregation. In...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2020.104389
更新日期:2020-12-01 00:00:00
abstract::This study deals with design and synthesis of novel benzofuran-pyrazole hybrids as anticancer agents. Eight compounds were chosen by National Cancer Institute (NCI), USA to evaluate their in vitro antiproliferative activity at 10(-5)M in full NCI 60 cell panel. The preliminary screening of the tested compounds showed ...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2015.08.006
更新日期:2015-12-01 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::Rapid emergence of drug resistance is crucial in management of HIV infection limiting implementation of efficacious drugs in the ART regimen. Designing new molecules against HIV drug resistant strains is utmost essential. Based on the anti-HIV-1 activity, we selected four 4-thiazolidinone derivatives (S009-1908, S009-...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2017.02.007
更新日期:2017-04-01 00:00:00
abstract::Five previously undescribed 4,5-seco-abietane rearrange diterpenoids (1-5, Prionidipene A-E) were isolated from the aerial parts of Salvia prionitis, along with thirteen known seco-abietane diterpenoids (6-18). The structures of 1-5 were elucidated mainly based on analysis of NMR and MS data. The absolute configuratio...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2018.08.040
更新日期:2018-12-01 00:00:00
abstract::New thiophene (2-13) and thienopyrimidine (15-27) derivatives have been synthesized. Twenty three compounds were screened against five cell lines namely; hepatocellular carcinoma (liver) HepG-2, epidermoid carcinoma (larynx) Hep-2, mammary gland (breast) MCF-7, human prostate cancer PC-3 and epithelioid cervix carcino...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2018.09.022
更新日期:2018-12-01 00:00:00
abstract::Seven new diterpenoids (1-7), including five 7-membered ring vibsane-type diterpenoids, vibsanolide A-E (1-5) and a pair of epimers of 14,15,16,17-tetranorvibsane-type diterpenoids possessing bicyclo[4.2.1]nonane moiety, vibsanolide F-G (6-7), together with twelve known analogues (8-19) were isolated from the crude ex...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2020.104498
更新日期:2021-01-01 00:00:00
abstract::Adenosine receptor antagonists are under investigation as potential drug candidates for the treatment of certain cancers, neurological disorders, depression and potentially improve tumour immunotherapy. The benzo-γ-pyrone scaffold is well-known in medicinal chemistry with diverse pharmacological activities attributed ...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2018.01.004
更新日期:2018-04-01 00:00:00
abstract::In continuation of our research program aiming at developing new potent antimicrobial agents, new series of substituted 3,4-dihydrothieno[2,3-d]pyrimidines was synthesized. The newly synthesized compounds were preliminary tested for their in vitro activity against six bacterial and three fungal strains using the agar ...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.102934
更新日期:2019-07-01 00:00:00
abstract::In an approach to develop potent cytotoxic compounds with targeted action, a systematic methodology was employed to design and initially synthesize parent compounds A1, A8, A13 and A14 followed by synthesis of further analogs of A1 (A2-A7) and A8 (A9-A12) with characterization by IR, NMR, mass and elemental techniques...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.103539
更新日期:2020-01-01 00:00:00
abstract::In addition to its catalytic domain, phosphoinsositide-dependent protein kinase-1 (PDK1) contains a C-terminal pleckstrin homology (PH) domain, which binds the membrane-bound phosphatidylinositol (3,4,5)-triphosphate [PI(3,4,5)P3] second messenger. Here, we report in vitro kinetic, phosphopeptide mapping, and oligomer...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2006.05.002
更新日期:2006-08-01 00:00:00
abstract::3-Azidobenzoates and 3-azidonitrobenzoates of 25-hydroxyvitamin D3 as well as 3-deoxy-3-azido-25-hydroxyvitamin D3 and 3-deoxy-3-azido-1,25-dihydroxyvitamin D3 were prepared as photoaffinity labels for vitamin D serum binding protein and 1,25-dihydroxyvitamin D3 intestinal receptor protein. The compounds prepared wer...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/0045-2068(86)90023-4
更新日期:1986-01-01 00:00:00
abstract::Inhibition of α-glucosidase is one of the important approaches in designing antidiabetic drugs for its role in decrease of the carbohydrates digestion to avoid post-prandial increase in blood sugar levels in diabetic patients. In the present study we designed a novel series of 2-acetylbenzofuran hydrazones (L1-L7) and...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2020.104082
更新日期:2020-09-01 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::The stilbenoid resveratrol (1) was subjected to regioselective acetylation catalysed by Candida antarctica lipase (CAL) to obtain 4'-acetylresveratrol (2). CAL biocatalysed regioselective alcoholysis of 3,5,4'-triacetylresveratrol (3), 3,5,4'-tributanoylresveratrol (6), and 3, 4, 5'-trioctanoylresveratrol (9) afforded...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2004.08.003
更新日期:2005-02-01 00:00:00
abstract::In this work a set of novel derivatives of parabanic acid 9a-d, 12a-d and 13a-d was synthesized and their anticonvulsant potential was evaluated. All the compounds under investigation exhibited anticonvulsant activity in both scPTZ and MES tests. In phase II anticonvulsant study, the trimethoxy phenyl derivative 9a ev...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.103473
更新日期:2020-01-01 00:00:00
abstract::Tumor hypoxia has been widely explored over the years as a diagnostic and therapeutic marker. Herein, we designed, optimized and synthesized a new multifunctional bioreductive linker (12) containing an alkynyl group (potential click chemistry fragment); the linker is based on 2-nitroimidazole which was expected to sim...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2020.103975
更新日期:2020-08-01 00:00:00
abstract::New series of hexahydroquinoline and fused quinoline derivatives were designed and synthesized. The thirty seven new compounds were screened for in vitro antitumor activity against HepG2, HCT-116 and MCF-7 cancer cells. Results indicated that compounds 2e, 2h, 5b, 5c, 6a, 7d and 9b have the strongest potency against t...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2020.104274
更新日期:2020-12-01 00:00:00
abstract::We report design and synthesis of set of novel anticancer agents based on caffeine-hydrazones bearing 2-hydroxyaryl- or 2-N-heteroaryl moiety. Anticancer activity evaluation using seven cancer cell lines and two non-malignant cell lines demonstrated that several derivatives display significant anticancer activity and ...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2015.03.003
更新日期:2015-06-01 00:00:00
abstract::Several new 5,6-dihydropyrimidine-2(1H)-thione derivatives have been prepared and investigated for their potencies for anticonvulsant activity against maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) test in mice. The acute neurotoxicity was measured by rotarod test. Compounds 3c and 3l were foun...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2017.07.017
更新日期:2017-10-01 00:00:00
abstract::2-Epi-jaspine B is an isomer of the natural product jaspine B and shows certain selectivity for SphK1 and potent antitumor activity. Based on the crystal structure of SphK1, we transformed the structure of 2-epi-jaspine B and modified the hydrophobic side chain to obtain a series of 2-epi-jaspine B analogs. The MTT as...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.103369
更新日期:2020-05-01 00:00:00
abstract::Tyrosinase inhibitors have become increasingly important as whitening agents and for the treatment of pigmentary disorders. In this study, the synthesis of kojic acid derivatives having 2-substituted-3-hydroxy-6-hyroxymethyl/chloromethyl/methyl/morpholinomethylpiperidinyl- methyl/pyrrolidinylmethyl-4H-pyran-4-one stru...
journal_title:Bioorganic chemistry
pub_type: 杂志文章
doi:10.1016/j.bioorg.2019.102950
更新日期:2019-07-01 00:00:00