(+/-)-3,4-Dihydroxy-8,9-methylenedioxypterocarpan and derivatives: cytotoxic effect on human leukemia cell lines.
Naturally occurring pterocarpans 1a,b, pterocarpan 1c, isoflavane 2 and ortho-quinone 3 were synthesized in the racemic form and their cytotoxic effect was evaluated on the human leukemia cell lines K562 (resistant to oxidative stress), Lucena-1 (MDR phenotype) and HL-60. Ortho-quinone 3 (IC(50)=1.5 microM, 1.8 microM and 0.2 microM, respectively) and catechol pterocarpan 1a (IC(50)=3.0 microM, 3.7 microM and 2.1 microM, respectively) were the most active compounds on these cells and were also evaluated on other human leukemia cell lines (Jurkat and Daudi). Ortho-quinone 3 was 2 to 10 times more potent than pterocarpan 1a, depending on the cell line considered, however, showed a greater toxicity for lymphocytes activated by PHA.
Netto
Chaquip D
CD
Laboratório de Química Bioorgânica (LQB), Núcleo de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Bloco H, Universidade Federal do Rio de Janeiro, RJ 21941-590, Brazil.
Santos
Eduardo S J
ES
Castro
Carolina Pereira
CP
da Silva
Alcides J M
AJ
Rumjanek
Vivian M
VM
Costa
Paulo R R
PR
D000970:Antineoplastic Agents / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D007938:Leukemia / Q000188:drug therapy*; D036343:Pterocarpans / Q000138:chemical synthesis* / Q000494:pharmacology; D011809:Quinones
C100482:3,4-dihydroxy-8,9-methylenedioxypterocarpan; D000970:Antineoplastic Agents; D001688:Biological Products; D036343:Pterocarpans; D011809:Quinones