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ABSTRACT: A series of novel N-linked diglycose derivatives 9 and 10 were conveniently and directly synthesized based on the key step of one-pot tandem Staudinger/aza-Wittig/reduction reaction from the azido sugar and sugar-derived aldehyde followed by deprotection. The biological activities against glycosidases (α-amylase, α-glucosidase, and β-glucosidase) and HIV-RT and antitumor activity of these compounds were preliminarily evaluated.
Carbohydrate research 02/2013; 372C:15-22. · 2.03 Impact Factor
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ABSTRACT: A series of phenanthrene imidazole with polyglycol side chain (2a-2c and 3a-3c) were synthesized and characterized by IR, NMR and MS. The cytotoxicity of 2a-2c and 3a-3c against cancer cell lines (HL-60, BGC-823, Bel-7402 and KB) in vitro were measured using MTT method. The DNA binding properties of 3a-3c were investigated by UV, fluorescence, CD spectroscopies and thermal denaturation. The results indicate that 2a exhibits higher cytotoxicity than cisplatin against BGC-823 and Bel-7402 cell lines, 3b and 3c exhibit higher cytotoxicity than 2b and 2c against BGC-823, Bel-7402 and KB cell lines. The cytotoxic effect of 2a-2c decrease with the increase of side chains length, the cytotoxic effect of 3a-3c increased with the increasing length of side chains against BGC-823, Bel-7402 and KB cell lines. Compounds 3a-3c intercalated DNA with a vertical orientation in the intercalation pocket. The binding constants of 3a-3c with Ct-DNA are 1.68×10(6), 1.51×10(6) and 0.709×10(6)M(-1), respectively. The binding affinity of 3a-3c with Ct-DNA trended to decrease with the increasing length of polyglycol side chains.
Bioorganic & medicinal chemistry letters 08/2012; 22(20):6347-51. · 2.65 Impact Factor
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ABSTRACT: A series of novel isoxazoline linked pseudodisaccharide derivatives were regiospecifically synthesized by 1,3-dipolar cycloaddition of α-allyl-C-glycopyranosides and sugar-derived nitrile oxides with good yields. The structures of the compounds were characterized by NMR spectroscopy and MS spectrometry and confirmed by the X-ray crystallographic analysis of compound ((5S)-3-(2,3-O-isopropylidene-5-deoxy-d-lyxofuranose-4-yl)isoxazoline-5-yl) methyl α- C-D-galactopyranoside. Their biological activities against glycosidases (α-amylase, α-glucosidase, and β-glucosidase) and HIV-RT, and antitumor activity were preliminarily evaluated. Some of them exhibited potent inhibitory activity to HIV-RT.
Carbohydrate research 04/2012; 351:7-16. · 2.03 Impact Factor
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ABSTRACT: A series of novel naphthalimide derivatives modified with various hydroxyl-alkylamines at 4-position have been synthesized. Their DNA binding properties were investigated by UV-Vis, fluoescence, and circular dichroism (CD) spectroscopies and thermal denaturation. The results showed that compounds 3a-e as the DNA intercalator exhibited middle binding affinities with Ct-DNA. The anticancer activities of 3a-e were preliminarily evaluated, compounds 3c and 3e exhibited potent anticancer activities against Bel-7402 cell line with IC(50) values of 5.57 and 9.17μM, respectively. More interestingly, enhancement of the fluorescence emission was found in the complexes of 3a-e with Ct-DNA, especially for 3c. This would make these compounds as potential DNA staining agents.
Bioorganic & medicinal chemistry letters 12/2011; 22(2):937-41. · 2.65 Impact Factor
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ABSTRACT: A series of novel ribonucleosides with C-5 OH replaced by a diaminopyrimidinyl group were synthesized by successively nucleophilic substitutions of 5'-deoxy-5'-amino-ribonucleosides with 2,4-dichloropyrimidine and then with various fatty amines under microwave irradiation. Their anticancer activities in vitro were preliminarily evaluated. Compounds 7a and 8a only exhibited anticancer activity against A549 cell line with the IC(50) values of 10.73 and 10.99 μM, respectively. In addition, 7h and 8h showed potent activities against both A549 and Hela cell lines with the IC(50) values of 12.71, 8.55 and 8.44, 5.55 μM, respectively.
Bioorganic & medicinal chemistry letters 02/2011; 21(3):916-9. · 2.65 Impact Factor
