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04555

Sigma-Aldrich

Trypanothione trifluoroacetate salt

≥98% (HPLC)

Sinonimo/i:

N1,N8-Bis(glutathionyl)spermidine disulfide

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About This Item

Formula empirica (notazione di Hill):
C27H47N9O10S2 · xC2HF3O2
Numero CAS:
96304-42-6
Peso molecolare:
721.85 (free base basis)
Beilstein:
3645155
Numero MDL:
MFCD17215942
Codice UNSPSC:
12352204
ID PubChem:
329747943
NACRES:
NA.32

Saggio

≥98% (HPLC)

Stato

powder or crystals

Solubilità

water: soluble 1 g/L

Temperatura di conservazione

−20°C

Stringa SMILE

OC(=O)C(F)(F)F.N[C@@H](CCC(=O)N[C@H]1CSSCC(NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(=O)NCCCNCCCCNC(=O)CNC1=O)C(O)=O

InChI

1S/C27H47N9O10S2.C2HF3O2/c28-16(26(43)44)4-6-20(37)35-18-14-47-48-15-19(36-21(38)7-5-17(29)27(45)46)25(42)34-13-23(40)32-11-3-9-30-8-1-2-10-31-22(39)12-33-24(18)41;3-2(4,5)1(6)7/h16-19,30H,1-15,28-29H2,(H,31,39)(H,32,40)(H,33,41)(H,34,42)(H,35,37)(H,36,38)(H,43,44)(H,45,46);(H,6,7)/t16-,17-,18-,19?;/m0./s1
BLTBWJNAZIKNTL-QZBRSAASSA-N

Azioni biochim/fisiol

Metabolite in the glutathione metabolism. A novel bis(glutathionyl)spermidine cofactor for glutathione reductase in trypanosomatids.

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Codice della classe di stoccaggio

13 - Non Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
BCCD2655
BCCC5464
BCCC1249
BCBZ5062
BCBX3817

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A H Fairlamb et al.
Annual review of microbiology, 46, 695-729 (1992-01-01)
Trypanosomatids differ from all other organisms in their ability to conjugate the sulfur-containing tripeptide, glutathione, and the polyamine, spermidine, to form trypanothione [N1,N8-bis(glutathionyl)spermidine]. Together with the NADPH-dependent flavoprotein, trypanothione reductase, the dithiol form of trypanothione provides an intracellular reducing environment
C Dumas et al.
The EMBO journal, 16(10), 2590-2598 (1997-05-15)
Parasitic protozoa belonging to the order Kinetoplastida contain trypanothione as their major thiol. Trypanothione reductase (TR), the enzyme responsible for maintaining trypanothione in its reduced form, is thought to be central to the redox defence systems of trypanosomatids. To investigate
A H Fairlamb et al.
Science (New York, N.Y.), 227(4693), 1485-1487 (1985-03-22)
Glutathione reductase from trypanosomes and leishmanias, unlike glutathione reductase from other organisms, requires an unusual low molecular weight cofactor for activity. The cofactor was purified from the insect trypanosomatid Crithidia fasciculata and identified as a novel glutathione-spermidine conjugate, N1,N8-bis(L-gamma-glutamyl-L-hemicystinyl-glycyl)spermidine, for
R Mukhopadhyay et al.
Proceedings of the National Academy of Sciences of the United States of America, 93(19), 10383-10387 (1996-09-17)
Leishmania resistant to arsenicals and antimonials extrude arsenite. Previous results of arsenite uptake into plasma membrane-enriched vesicles suggested that the transported species is a thiol adduct of arsenite. In this paper, we demonstrate that promastigotes of arsenite-resistant Leishmania tarentolae have
Abdulsalam A M Alkhaldi et al.
Molecular pharmacology, 87(3), 451-464 (2014-12-21)
We have previously reported that curcumin analogs with a C7 linker bearing a C4-C5 olefinic linker with a single keto group at C3 (enone linker) display midnanomolar activity against the bloodstream form of Trypanosoma brucei. However, no clear indication of

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