Glutathione-like tripeptides as inhibitors of glutathionylspermidine synthetase.: Part 1: Substitution of the glycine carboxylic acid group

Katie Amssoms; Sandra Oza; Esteban Ravaschino; Abdellah Yamani; Anne Marie Lambeir; Padinchare Rajan; Gunther Bal; Juan Bautista Rodriguez; Alan H. Fairlamb; Achiel Haemers

doi:10.1016/S0960-894X(02)00489-4

Glutathione-like tripeptides as inhibitors of glutathionylspermidine synthetase. Part 1: Substitution of the glycine carboxylic acid group

Katie Amssoms, Sandra Oza, Esteban Ravaschino, Abdellah Yamani, Anne Marie Lambeir, Padinchare Rajan, Gunther Bal, Juan Bautista Rodriguez, Alan H. Fairlamb, Achiel Haemers (Lead / Corresponding author)

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Abstract

Glutathionylspermidine synthetase/amidase (GspS) is an essential enzyme in the biosynthesis and turnover of trypanothione and represents an attractive target for the design of selective anti-parasitic drugs. We synthesised a series of analogues of glutathione (L-γ-Glu-L-Leu-Gly-X) where the glycine carboxylic acid group (X) has been substituted for other acidic groups such as tetrazole, hydroxamic acid, acylsulphonamide and boronic acid. The boronic acid appears the most promising lead compound (IC₅₀ of 17.2 µM).

Original language	English
Pages (from-to)	2553-2556
Number of pages	4
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	12
Issue number	18
DOIs	https://doi.org/10.1016/S0960-894X(02)00489-4
Publication status	Published - 16 Sept 2002

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Amssoms, K., Oza, S., Ravaschino, E., Yamani, A., Lambeir, A. M., Rajan, P., Bal, G., Rodriguez, J. B., Fairlamb, A. H., & Haemers, A. (2002). Glutathione-like tripeptides as inhibitors of glutathionylspermidine synthetase. Part 1: Substitution of the glycine carboxylic acid group. Bioorganic & Medicinal Chemistry Letters, 12(18), 2553-2556. https://doi.org/10.1016/S0960-894X(02)00489-4

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title = "Glutathione-like tripeptides as inhibitors of glutathionylspermidine synthetase.: Part 1: Substitution of the glycine carboxylic acid group",

abstract = "Glutathionylspermidine synthetase/amidase (GspS) is an essential enzyme in the biosynthesis and turnover of trypanothione and represents an attractive target for the design of selective anti-parasitic drugs. We synthesised a series of analogues of glutathione (L-γ-Glu-L-Leu-Gly-X) where the glycine carboxylic acid group (X) has been substituted for other acidic groups such as tetrazole, hydroxamic acid, acylsulphonamide and boronic acid. The boronic acid appears the most promising lead compound (IC50 of 17.2 µM).",

author = "Katie Amssoms and Sandra Oza and Esteban Ravaschino and Abdellah Yamani and Lambeir, {Anne Marie} and Padinchare Rajan and Gunther Bal and Rodriguez, {Juan Bautista} and Fairlamb, {Alan H.} and Achiel Haemers",

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Amssoms, K, Oza, S, Ravaschino, E, Yamani, A, Lambeir, AM, Rajan, P, Bal, G, Rodriguez, JB, Fairlamb, AH & Haemers, A 2002, 'Glutathione-like tripeptides as inhibitors of glutathionylspermidine synthetase. Part 1: Substitution of the glycine carboxylic acid group', Bioorganic & Medicinal Chemistry Letters, vol. 12, no. 18, pp. 2553-2556. https://doi.org/10.1016/S0960-894X(02)00489-4

TY - JOUR

T1 - Glutathione-like tripeptides as inhibitors of glutathionylspermidine synthetase.

T2 - Part 1: Substitution of the glycine carboxylic acid group

AU - Amssoms, Katie

AU - Oza, Sandra

AU - Ravaschino, Esteban

AU - Yamani, Abdellah

AU - Lambeir, Anne Marie

AU - Rajan, Padinchare

AU - Bal, Gunther

AU - Rodriguez, Juan Bautista

AU - Fairlamb, Alan H.

AU - Haemers, Achiel

PY - 2002/9/16

Y1 - 2002/9/16

N2 - Glutathionylspermidine synthetase/amidase (GspS) is an essential enzyme in the biosynthesis and turnover of trypanothione and represents an attractive target for the design of selective anti-parasitic drugs. We synthesised a series of analogues of glutathione (L-γ-Glu-L-Leu-Gly-X) where the glycine carboxylic acid group (X) has been substituted for other acidic groups such as tetrazole, hydroxamic acid, acylsulphonamide and boronic acid. The boronic acid appears the most promising lead compound (IC50 of 17.2 µM).

AB - Glutathionylspermidine synthetase/amidase (GspS) is an essential enzyme in the biosynthesis and turnover of trypanothione and represents an attractive target for the design of selective anti-parasitic drugs. We synthesised a series of analogues of glutathione (L-γ-Glu-L-Leu-Gly-X) where the glycine carboxylic acid group (X) has been substituted for other acidic groups such as tetrazole, hydroxamic acid, acylsulphonamide and boronic acid. The boronic acid appears the most promising lead compound (IC50 of 17.2 µM).

U2 - 10.1016/S0960-894X(02)00489-4

DO - 10.1016/S0960-894X(02)00489-4

M3 - Article

SN - 0960-894X

VL - 12

SP - 2553

EP - 2556

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 18

ER -

Glutathione-like tripeptides as inhibitors of glutathionylspermidine synthetase. Part 1: Substitution of the glycine carboxylic acid group

Abstract

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