Title

Synthesis And Biological Evaluation Of Dihydromotuporamine Derivatives In Cells Containing Active Polyamine Transporters

Abstract

Dihydromotuporamine C (4) and its 4,4-triamine analogue (5) were synthesized in good yield using ring-closing metathesis (RCM) methods. Comparison of their biological activities (Ki determinations in L1210 cells and IC50 determinations in L1210, CHO, and CHO-MG cells) revealed that the motuporamine derivatives do not use the polyamine transporter (PAT) for cellular entry. Bioevaluation of a N1-(anthracen-9- ylmethyl)-n1-(ethyl)homospermidine control (7) revealed that the presence of a N1 tertiary amine center imparted a significant reduction in the PAT affinity of the polyamine conjugate and abolished its PAT-targeting selectivity. © 2005 American Chemical Society.

Publication Date

6-2-2005

Publication Title

Journal of Medicinal Chemistry

Volume

48

Issue

11

Number of Pages

3832-3839

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1021/jm0491288

Socpus ID

20144363253 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/20144363253

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