Dataset Information

Synthesis and Biological Activities of 5-Thio-?-GalCers.

ABSTRACT: NKT cells, a unique subset of T cells that recognizes glycolipid antigens presented by CD1d molecules, are believed to produce key cytokines of both Th1 and Th2 T cells and are thus involved in the control of several types of immune response. As an active glycolipid antigen having ?-galactosyl ceramide core structure, KRN7000 showed promising immunostimulation activity and was selected as an anticancer drug candidate for further clinical application. In this report, three new KRN7000 structural analogues were designed and synthesized, in which the ring oxygen of the galactopyranose residue is replaced by a sulfur atom along with the variation on the lipid chain. Their abilities for stimulating mouse NKT cells to produce IFN-? and IL-4 were evaluated both in vivo and in vitro.

SUBMITTER: Bi J

PROVIDER: S-EPMC4416434 | biostudies-literature | 2015 Apr

REPOSITORIES: biostudies-literature

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Synthesis and Biological Activities of 5-Thio-α-GalCers.

Bi Jingjing J Wang Jing J Zhou Kai K Wang Yuancheng Y Fang Min M Du Yuguo Y

ACS medicinal chemistry letters 20150211 4

NKT cells, a unique subset of T cells that recognizes glycolipid antigens presented by CD1d molecules, are believed to produce key cytokines of both Th1 and Th2 T cells and are thus involved in the control of several types of immune response. As an active glycolipid antigen having α-galactosyl ceramide core structure, KRN7000 showed promising immunostimulation activity and was selected as an anticancer drug candidate for further clinical application. In this report, three new KRN7000 structural ...[more]

PMID: 25941558

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Project description:: A series of sixteen ring-substituted N-arylcinnamamides was prepared and characterized. Primary in vitro screening of all the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra, Fusarium avenaceum, and Bipolaris sorokiniana. Several of the tested compounds showed antistaphylococcal, antitubercular, and antifungal activities comparable with or higher than those of ampicillin, isoniazid, and benomyl. (2E)-N-[3,5-bis(trifluoromethyl)phenyl]-3-phenylprop-2-enamide and (2E)-3-phenyl-N-[3-(trifluoromethyl)phenyl]prop-2-enamide showed the highest activities (MICs = 22.27 and 27.47 µM, respectively) against all four staphylococcal strains and against M.tuberculosis. These compounds showed an activity against biofilm formation of S.aureus ATCC 29213 in concentrations close to MICs and an ability to increase the activity of clinically used antibiotics with different mechanisms of action (vancomycin, ciprofloxacin, and tetracycline). In time-kill studies, a decrease of CFU/mL of >99% after 8 h from the beginning of incubation was observed. (2E)-N-(3,5-Dichlorophenyl)- and (2E)-N-(3,4-dichlorophenyl)-3-phenylprop-2-enamide had a MIC = 27.38 µM against M. tuberculosis, while a significant decrease (22.65%) of mycobacterial cell metabolism determined by the MTT assay was observed for the 3,5-dichlorophenyl derivative. (2E)-N-(3-Fluorophenyl)- and (2E)-N-(3-methylphenyl)-3-phenylprop-2-enamide exhibited MICs = 16.58 and 33.71 µM, respectively, against B. sorokiniana. The screening of the cytotoxicity of the most effective antimicrobial compounds was performed using THP-1 cells, and these chosen compounds did not shown any significant lethal effect. The compounds were also evaluated for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. (2E)-N-(3,5-dichlorophenyl)-3-phenylprop-2-enamide (IC50 = 5.1 µM) was the most active PET inhibitor. Compounds with fungicide potency did not show any in vivo toxicity against Nicotiana tabacum var. Samsun. The structure?activity relationships are discussed.

Dataset Information

Synthesis and Biological Activities of 5-Thio-?-GalCers.

Publications

Synthesis and Biological Activities of 5-Thio-α-GalCers.

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