- Solid phase applications of Dde and the analogue Nde: Synthesis of trypanothione disulphide
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Bis - Dde and Nde spermidine derivatives selectively protected on the primary amines were readily prepared and attached via the secondary amine group to a p-nitrophenyl-1-chloroformate pre-activated HMPA resin. Deprotection for Nde was monitored by colour
- Kellam, Barrie,Bycroft, Barrie W.,Chhabra, Siri Ram
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- 5-Substituted 3-chlorokenpaullone derivatives are potent inhibitors of Trypanosoma brucei bloodstream forms
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Trypanothione synthetase is an essential enzyme for kinetoplastid parasites which cause highly disabling and fatal diseases in humans and animals. Inspired by the observation that N(5)-substituted paullones inhibit the trypanothione synthetase from the related parasite Leishmania infantum, we designed and synthesized a series of new derivatives. Although none of the new compounds displayed strong inhibition of Trypanosoma brucei trypanothione synthetase, several of them caused a remarkable growth inhibition of cultivated Trypanosoma brucei bloodstream forms. The most potent congener 3a showed antitrypanosomal activity in double digit nanomolar concentrations and a selectivity index of three orders of magnitude versus murine macrophage cells.
- Orban, Oliver C.F.,Korn, Ricarda S.,Benítez, Diego,Medeiros, Andrea,Preu, Lutz,Loa?c, Nadège,Meijer, Laurent,Koch, Oliver,Comini, Marcelo A.,Kunick, Conrad
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p. 3790 - 3800
(2016/07/20)
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- Solid phase synthesis of polyamine conjugates for the study of trypanothione reductase
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A number of polyamine scaffolds were synthesised, enabling the facile preparation of a variety of polyamine conjugates using both Boc and Fmoc protecting group strategies. Products were released from the solid support by treatment with either triflic acid/trifluoroacetic acid or trifluoroacetic acid. The trypanosomal metabolite N1, N6-bis(glurathionyl)spermidine [trypanothione], and a range of related analogues were prepared for biological evaluation as previously communicated.
- Marsh, Ian R.,Bradley, Mark
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p. 17317 - 17334
(2007/10/03)
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- Synthesis and NMR Characterization of the Trypanosomatid Metabolite, N1,N8-Bis(glutathionyl)spermidine Disulphide (Trypanothione Disulphide)
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An optimized chemical synthesis of the novel trypanosomatid metabolite, N1,N8-bis(glutathionyl)spermidine (trypanothione disulphide) is described, and its solution structure has been investigated by NMR spectroscopy.The 1H, 13C, and
- Henderson, Graeme B.,Glushka, John,Cowburn, David,Cerami, Anthony
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p. 911 - 914
(2007/10/02)
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- Synthesis of the Trypanosomatid Metabolites Trypanothione, and N1-Mono- and N8-Mono-glutathionylspermidine
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The trypanosomatid metabolite trypanothione 1,N8-bis(glutathionyl)spermidine> and its biosynthetic co-metabolites the isomeric N1- and N8-mono-glutathionylspermidines have been synthesised by a mild route whic
- Henderson, Graeme B.,Ulrich, Peter,Fairlamb, Alan H.,Cerami, Anthony
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p. 593 - 594
(2007/10/02)
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