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ID: ALA1149564

Journal: Bioorg Med Chem Lett

Title: Synthesis and bioevaluation of N-(arylalkyl)-homospermidine conjugates.

Authors: Xie S, Cheng P, Liu G, Ma Y, Zhao J, Chehtane M, Khaled AR, Phanstiel O, Wang C.

Abstract: N1-(Arylalkyl)homospermidines (1c-1f) and terminally piperazine-substituted homospermidine conjugates (2a-2e) were synthesized and evaluated for cytotoxicity in mouse leukemia L1210, alpha-difluoromethylornithine (DFMO)-treated L1210, melanoma B16, spermidine (SPD)-treated B16, 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 pro-B 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 1a.

CiteXplore: 17574415

DOI: 10.1016/j.bmcl.2007.06.009