Synthesis and Characterization of a Fluorescent Analogue of Methotrexate

A. Ashok Kumar; James H. Freisheim; Robert J. Kempton; Gregory M. Anstead; Angelique M. Black; Larry Judge

doi:10.1021/jm00355a023

Synthesis and Characterization of a Fluorescent Analogue of Methotrexate

A. Ashok Kumar, James H. Freisheim, Robert J. Kempton, Gregory M. Anstead, Angelique M. Black, Larry Judge

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

17 Scopus citations

Abstract

The lysine analogue (4) of methotrexate (1) was treated with 5-(dimethylamino)naphthalene-l-sulfonyl chloride to give the corresponding dansyl analogue 5. The product isolated by preparative TLC was further purified on a preparative HPLC column. Analogue 5 exhibited fluorescence properties characteristic of the dansyl moiety and was a potent inhibitor of dihydrofolate reductase purified from Lactobacillus casei, chicken liver, and a human lymphoblastoid cell line.

Original language	English (US)
Pages (from-to)	111-113
Number of pages	3
Journal	Journal of Medicinal Chemistry
Volume	26
Issue number	1
DOIs	https://doi.org/10.1021/jm00355a023
State	Published - Jan 1983
Externally published	Yes

ASJC Scopus subject areas

Drug Discovery
Molecular Medicine

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abstract = "The lysine analogue (4) of methotrexate (1) was treated with 5-(dimethylamino)naphthalene-l-sulfonyl chloride to give the corresponding dansyl analogue 5. The product isolated by preparative TLC was further purified on a preparative HPLC column. Analogue 5 exhibited fluorescence properties characteristic of the dansyl moiety and was a potent inhibitor of dihydrofolate reductase purified from Lactobacillus casei, chicken liver, and a human lymphoblastoid cell line.",

author = "Kumar, {A. Ashok} and Freisheim, {James H.} and Kempton, {Robert J.} and Anstead, {Gregory M.} and Black, {Angelique M.} and Larry Judge",

year = "1983",

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AU - Kumar, A. Ashok

AU - Freisheim, James H.

AU - Kempton, Robert J.

AU - Anstead, Gregory M.

AU - Black, Angelique M.

AU - Judge, Larry

PY - 1983/1

Y1 - 1983/1

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AB - The lysine analogue (4) of methotrexate (1) was treated with 5-(dimethylamino)naphthalene-l-sulfonyl chloride to give the corresponding dansyl analogue 5. The product isolated by preparative TLC was further purified on a preparative HPLC column. Analogue 5 exhibited fluorescence properties characteristic of the dansyl moiety and was a potent inhibitor of dihydrofolate reductase purified from Lactobacillus casei, chicken liver, and a human lymphoblastoid cell line.

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Synthesis and Characterization of a Fluorescent Analogue of Methotrexate

Abstract

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