Synthesis and bioevaluation of N-(arylalkyl)-homospermidine conjugates
Abbreviated Journal Title
Bioorg. Med. Chem. Lett.
homospermidine; polyamine conjugate; synthesis; apoptosis; ACTIVE POLYAMINE TRANSPORTERS; MOLECULAR REQUIREMENTS; BIOLOGICAL; EVALUATION; SELECTIVE DELIVERY; CANCER CELLS; HOMOLOGATION; DERIVATIVES; ANALOGS; AGENTS; Chemistry, Medicinal; Chemistry, Organic
N'-(Arylalkyl)homospermidines (Ic-1f) and terminally piperazine-substituted homospermidine conjugates (2a-2e) were synthesized and evaluated for cytotoxicity in mouse leukemia L 1210, alpha-difluorometliylornithine (DFMO)-treated L 12 10, melanoma B 16, spermidine (SPD)-treated B 16, and HeLa cell lines. Results demonstrated that homospermidine was a more effective vector than piperazine-substituted homospermidine in ferrying diverse arenes into cells via the polyamine transporter. The leading compound, 9-anthracenemethyl-homospermidine (1a), was shown to induce apoptosis in B16 cells and IL-3 dependent FL5.12A proB cells. The novel conjugate 4-biphenylmethyl-homospermidine (1e) could also induce apoptosis. However, it exhibited different effect on the cell cycle of B16 cells compared to la. (c) 2007 Elsevier Ltd. All rights reserved.
Bioorganic & Medicinal Chemistry Letters
"Synthesis and bioevaluation of N-(arylalkyl)-homospermidine conjugates" (2007). Faculty Bibliography 2000s. 7806.