Preliminary evaluation of the cytotoxicity of a series of tris-2-aminoethylamine (Tren) based hexadentate heterocyclic donor agents

Suzy V. Torti; Rong Ma; Vincent J. Venditto; Frank M. Torti; Roy P. Planalp; Martin W. Brechbiel

doi:10.1016/j.bmc.2005.07.007

Preliminary evaluation of the cytotoxicity of a series of tris-2-aminoethylamine (Tren) based hexadentate heterocyclic donor agents

Suzy V. Torti, Rong Ma, Vincent J. Venditto, Frank M. Torti, Roy P. Planalp, Martin W. Brechbiel

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

Tachpyridine is a cytotoxic metal chelator with potential anti-tumor activity. The synthesis and evaluation of a set of derivatives of the related hexadentate heterocyclic donor agents tris-2-aminoethylamine (tren) and tris[N-(2-pyridylmethylene)-2-aminoethyl]amine (trenpyr) was performed to compare their cytotoxic activity to tachpyridine in HeLa tumor cells. Methyl groups were added to the pyridyl ring of trenpyr, and the effects of alkyl group substitution on cell survival were assessed. Profound cytotoxicity was observed and IC₅₀ data were obtained in ascending order from those compounds substituted with a methyl group at the 3-, 4-, or 5-position and lastly by the 6-methyl derivative. These results suggest that analogous derivatives with substitution at the 3-position of the pyridyl ring deserve further exploration.

Original language	English
Pages (from-to)	5961-5967
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	13
Issue number	21
DOIs	https://doi.org/10.1016/j.bmc.2005.07.007
State	Published - Nov 1 2005

Bibliographical note

Funding Information:
This work was supported in part by grant No. DK 57781 (S.V.T.) from the National Institutes of Health. This research was supported in part by the Intramural Research Program of the NIH, National Cancer Institute, Center for Cancer Research.

Funding

This work was supported in part by grant No. DK 57781 (S.V.T.) from the National Institutes of Health. This research was supported in part by the Intramural Research Program of the NIH, National Cancer Institute, Center for Cancer Research.

Funders	Funder number
Center for Cancer Research
National Institutes of Health (NIH)
National Institute of Mental Health	Z01MH002793
National Childhood Cancer Registry – National Cancer Institute

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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title = "Preliminary evaluation of the cytotoxicity of a series of tris-2-aminoethylamine (Tren) based hexadentate heterocyclic donor agents",

abstract = "Tachpyridine is a cytotoxic metal chelator with potential anti-tumor activity. The synthesis and evaluation of a set of derivatives of the related hexadentate heterocyclic donor agents tris-2-aminoethylamine (tren) and tris[N-(2-pyridylmethylene)-2-aminoethyl]amine (trenpyr) was performed to compare their cytotoxic activity to tachpyridine in HeLa tumor cells. Methyl groups were added to the pyridyl ring of trenpyr, and the effects of alkyl group substitution on cell survival were assessed. Profound cytotoxicity was observed and IC50 data were obtained in ascending order from those compounds substituted with a methyl group at the 3-, 4-, or 5-position and lastly by the 6-methyl derivative. These results suggest that analogous derivatives with substitution at the 3-position of the pyridyl ring deserve further exploration.",

author = "Torti, {Suzy V.} and Rong Ma and Venditto, {Vincent J.} and Torti, {Frank M.} and Planalp, {Roy P.} and Brechbiel, {Martin W.}",

note = "Funding Information: This work was supported in part by grant No. DK 57781 (S.V.T.) from the National Institutes of Health. This research was supported in part by the Intramural Research Program of the NIH, National Cancer Institute, Center for Cancer Research.",

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AU - Torti, Suzy V.

AU - Ma, Rong

AU - Venditto, Vincent J.

AU - Torti, Frank M.

AU - Planalp, Roy P.

AU - Brechbiel, Martin W.

N1 - Funding Information: This work was supported in part by grant No. DK 57781 (S.V.T.) from the National Institutes of Health. This research was supported in part by the Intramural Research Program of the NIH, National Cancer Institute, Center for Cancer Research.

PY - 2005/11/1

Y1 - 2005/11/1

N2 - Tachpyridine is a cytotoxic metal chelator with potential anti-tumor activity. The synthesis and evaluation of a set of derivatives of the related hexadentate heterocyclic donor agents tris-2-aminoethylamine (tren) and tris[N-(2-pyridylmethylene)-2-aminoethyl]amine (trenpyr) was performed to compare their cytotoxic activity to tachpyridine in HeLa tumor cells. Methyl groups were added to the pyridyl ring of trenpyr, and the effects of alkyl group substitution on cell survival were assessed. Profound cytotoxicity was observed and IC50 data were obtained in ascending order from those compounds substituted with a methyl group at the 3-, 4-, or 5-position and lastly by the 6-methyl derivative. These results suggest that analogous derivatives with substitution at the 3-position of the pyridyl ring deserve further exploration.

AB - Tachpyridine is a cytotoxic metal chelator with potential anti-tumor activity. The synthesis and evaluation of a set of derivatives of the related hexadentate heterocyclic donor agents tris-2-aminoethylamine (tren) and tris[N-(2-pyridylmethylene)-2-aminoethyl]amine (trenpyr) was performed to compare their cytotoxic activity to tachpyridine in HeLa tumor cells. Methyl groups were added to the pyridyl ring of trenpyr, and the effects of alkyl group substitution on cell survival were assessed. Profound cytotoxicity was observed and IC50 data were obtained in ascending order from those compounds substituted with a methyl group at the 3-, 4-, or 5-position and lastly by the 6-methyl derivative. These results suggest that analogous derivatives with substitution at the 3-position of the pyridyl ring deserve further exploration.

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JO - Bioorganic and Medicinal Chemistry

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ER -

Preliminary evaluation of the cytotoxicity of a series of tris-2-aminoethylamine (Tren) based hexadentate heterocyclic donor agents

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

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