Title

Synthesis and bioevaluation of N-(arylalkyl)-homospermidine conjugates

Authors

Authors

S. Q. Xie; P. F. Cheng; G. C. Liu; Y. F. Ma; J. Zhao; M. Chehtane; A. R. Khaled; O. Phanstiel;C. J. Wang

Comments

Authors: contact us about adding a copy of your work at STARS@ucf.edu

Abbreviated Journal Title

Bioorg. Med. Chem. Lett.

Keywords

homospermidine; polyamine conjugate; synthesis; apoptosis; ACTIVE POLYAMINE TRANSPORTERS; MOLECULAR REQUIREMENTS; BIOLOGICAL; EVALUATION; SELECTIVE DELIVERY; CANCER CELLS; HOMOLOGATION; DERIVATIVES; ANALOGS; AGENTS; Chemistry, Medicinal; Chemistry, Organic

Abstract

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.

Journal Title

Bioorganic & Medicinal Chemistry Letters

Volume

17

Issue/Number

16

Publication Date

1-1-2007

Document Type

Article

Language

English

First Page

4471

Last Page

4475

WOS Identifier

WOS:000248877800013

ISSN

0960-894X

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