Polyamine conjugates of stigmasterol

Three new polyamine conjugates with stigmasterol [(3β,22E)-stigmasta-5,22-dien-3-ol] were synthesized and subjected to basic antimicrobial and cytotoxic tests. The conjugate derived from spermine, (3β,22E)-stigmasta-5,22-dien-3-yl 4(12-amino-4,9-diaza-dodecylamino)-4-oxobutanoate (5c), displayed considerable antimicrobial activity on Staphylococcus aureus at low concentration (50 μg mL−1). The cytotoxic activity was tested on cells of human T-lymfoblastic leukemia (IC50 = 35.8 ± 10.3 μM (5c) and IC50 = 35.9 ± 5.7 μM (5b)) and normal human fibroblasts (IC50 = 38.0 ± 2.8 μM (5c) and IC50 = 45.5 ± 1.9 μM (5b)). Conjugate 5a displayed no activity in both tests.

Three new polyamine conjugates with stigmasterol [(3β,22E)-stigmasta-5,22-dien-3-ol] were synthesized a subjected to basic antimicrobial and cytotoxic tests. (3β,22E)-Stigmasta-5,22-dien-3-yl 4(12-amino-4,9-diaza-dodecylamino)-4-oxobutanoate (5c) displayed considerable antimicrobial activity on Staphylococcus aureus at low concentration (50 μg mL−1), and cytotoxic activity on cells of human T-lymfoblastic leukemia (IC50 = 35.8 ± 10.3 μM). Cytotoxicity values of 5b were higher than those of the parent piperazine. Calculation shows the illustration geometry of 5c.Figure optionsDownload as PowerPoint slideHighlights
► New polyamine conjugates of stigmasterol.
► Cytotoxic activity against human T-lymfoblastic leukemia.
► Pro-drug concept for slow release of polyamines from their conjugates.
► Antimicrobial activity on Staphylococcus aureus.
► Physico-chemical parameters for pharmacology applications.