Synthesis and biological activities of indolocarbazoles bearing amino acid residues.
Three indolocarbazole compounds bearing a tripeptide or a lysine group attached to one of the indole nitrogens via a propylamino chain and two rebeccamycin derivatives bearing a lysine residue on the sugar moiety were synthesised with the aim of improving the binding to DNA and the antiproliferative activities. Four tumour cell lines, from murine L1210 leukemia, human HT29 colon carcinoma, A549 non-small cell lung carcinoma and K-562 leukemia, were used to evaluate the cytotoxicity of the drugs. Their effects on the cell cycle of L1210 cells and their antimicrobial properties against two Gram-positive bacteria Bacillus cereus and Streptomyces chartreusis, a Gram-negative bacterium Escherichia coli and a yeast Candida albicans were also investigated.
Moreau
P
P
Laboratoire SEESIB, Université Blaise Pascal, UMR 6504 du CNRS, 24 avenue des Landais, F-63177 Aubière Cedex, France.
Sancelme
M
M
Bailly
C
C
Léonce
S
S
Pierré
A
A
Hickman
J
J
Pfeiffer
B
B
Prudhomme
M
M
D000596:Amino Acids / Q000737:chemistry; D000617:Aminoglycosides; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001409:Bacillus cereus / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D002227:Carbazoles / Q000737:chemistry; D002289:Carcinoma, Non-Small-Cell Lung; D002453:Cell Cycle / Q000187:drug effects; D002455:Cell Division / Q000187:drug effects; D003110:Colonic Neoplasms; D004926:Escherichia coli / Q000187:drug effects; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007938:Leukemia; D008175:Lung Neoplasms; D051379:Mice; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013302:Streptomyces / Q000187:drug effects; D014407:Tumor Cells, Cultured
C450183:12-(2-O-lysyl-4-O-methyl-glucopyranosyl)-6,7,12,13-tetrahydro(5H)-indolo(2,3-a)-pyrrolo(3,4-c)carbazole-5,7-dione dihydrochloride; D000596:Amino Acids; D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D002227:Carbazoles; D007211:Indoles; D009005:Monosaccharides; C075954:indolo(3,2-b)carbazole; C053339:rebeccamycin