title: Preparation of betulinic acid derivatives by chemical and biotransformation methods and determination of cytotoxicity against selected cancer cell lines.
abstract: Several novel 2,4-dinitrophenylhydrazone betulinic acid derivatives have been prepared by chemical and biotransformation methods using fungi and carrot cells. Some compounds showed significant cytotoxicity and selectivity against some tumor cell lines. The most active, 3-[(2,4-dinitrophenyl)hydrazono]lup-(20R)-29-oxolupan-28-oic acid, showed IC50 values between 1.76 and 2.51 μM against five human cancer cell lines. The most selective, 3-hydroxy-20-[(2,4-dinitrophenyl)hydrazono]-29-norlupan-28-oic acid, was five to seven times more selective for cancer cells when compared to fibroblasts. Cell cycle analysis and apoptosis induction were studied for the most active derivatives.
authors: Departamento de Química, Universidade Federal do Paraná, Centro Politécnico, 81531-970, CP 19081 Curitiba, PR, Brazil.
authors: Leopoldo C
authors: LC
authors: Baratto
authors: Mariana V
authors: MV
authors: Porsani
authors: Ida C
authors: IC
authors: Pimentel
authors: Adaucto B
authors: AB
authors: Pereira Netto
authors: Reinhard
authors: R
authors: Paschke
authors: Brás H
authors: BH
authors: Oliveira
mesh_terms: D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D005434:Flow Cytometry; D006801:Humans; D006835:Hydrazones / Q000737:chemistry* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D053978:Pentacyclic Triterpenes; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D000094062:Betulinic Acid
chemical_list: C000590553:3-((2,4-dinitrophenyl)hydrazono)lup-29-oxolupan-28-oic acid; D006835:Hydrazones; D053978:Pentacyclic Triterpenes; D014315:Triterpenes; D000094062:Betulinic Acid
keywords: Antitumor activity; Betulinic acid; Biotransformation; Cytotoxicity; SRB assay