PMID: 11606128Oct 19, 2001Paper

Amino acid/spermine conjugates: polyamine amides as potent spermidine uptake inhibitors

Journal of Medicinal Chemistry
M R BurnsG F Graminski

Abstract

In this paper we describe the synthesis and characterization of a series of simple spermine/amino acid conjugates, some of which potently inhibit the uptake of spermidine into MDA-MB-231 breast cancer cells. The presence of an amide in the functionalized polyamine appeared to add to the affinity for the polyamine transporter. The extensive biological characterization of an especially potent analogue from this series, the Lys-Spm conjugate (31), showed this molecule will be an extremely useful tool for use in polyamine research. It was shown that the use of 31 in combination with DFMO led to a cytostatic growth inhibition of a variety of cancer cells, even when used in the presence of an extracellular source of transportable spermidine. It was furthermore shown that this combination effectively reduced the cellular levels of putrescine and spermidine while not affecting the levels of spermine. These facts together with the nontoxic nature of 31 make it a novel lead for further anticancer development.

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Citations

Mar 10, 2005·Bioorganic & Medicinal Chemistry·Mark R BurnsSunil A David
Dec 12, 2001·Bioorganic & Medicinal Chemistry Letters·Gerard F GraminskiMark R Burns
Sep 3, 2003·Bioorganic & Medicinal Chemistry Letters·Laurence CovassinRichard Poulin
Jan 11, 2014·Journal of Medicinal Chemistry·Aaron MuthOtto Phanstiel
Mar 10, 2007·Biochemical and Biophysical Research Communications·Toshiyuki ItoAkira Shirahata
Aug 21, 2003·Journal of Cellular and Molecular Medicine·Thresia Thomas, T J Thomas
May 24, 2005·Comparative Biochemistry and Physiology. Toxicology & Pharmacology : CBP·Rosa María RegueraRafael Balaña-Fouce
Dec 13, 2002·Rapid Communications in Mass Spectrometry : RCM·Changjin ZhuYufen Zhao
Apr 3, 2003·Rapid Communications in Mass Spectrometry : RCM·Changjin ZhuYufen Zhao
Jul 25, 2009·Rapid Communications in Mass Spectrometry : RCM·Jingjing DingYufen Zhao
Dec 7, 2005·International Journal of Cancer. Journal International Du Cancer·Yan ChenThomas G O'Brien
May 4, 2007·American Journal of Physiology. Cell Physiology·Masato IsomeJoseph Satriano
Dec 4, 2003·Journal of Medicinal Chemistry·Raymond J BergeronWilliam R Weimar
Jul 13, 2021·The International Journal of Biochemistry & Cell Biology·Aiste DobrovolskaiteOtto Phanstiel
Jan 6, 2006·Journal of Medicinal Chemistry·Jean-Guy DelcrosPhilippe Uriac
Dec 9, 2010·Journal of Medicinal Chemistry·Xiong-Jie JiangDennis K P Ng
Oct 12, 2010·Journal of Medicinal Chemistry·Sophie TomasiJean-Guy Delcros
Feb 14, 2006·The Journal of Physical Chemistry. B·Sun McMasters, Lisa A Kelly

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