CAS 96304-42-6

Trypanothione

Description:

Trypanothione is a naturally occurring thiol compound that plays a crucial role in the redox biology of certain parasitic organisms, particularly within the Trypanosomatidae family, which includes the pathogens responsible for diseases such as sleeping sickness and Chagas disease. Structurally, trypanothione is a conjugate of glutathione and a spermidine derivative, featuring a unique disulfide bond that contributes to its antioxidant properties. It functions primarily as a reducing agent, helping to maintain cellular redox balance and protect against oxidative stress. Trypanothione is involved in various biochemical processes, including detoxification of reactive oxygen species and regulation of cellular signaling pathways. Its presence is particularly significant in the context of drug resistance in trypanosomatid parasites, as it can influence the efficacy of certain antiprotozoal treatments. The compound's unique characteristics and functions make it a subject of interest in both biochemistry and pharmacology, particularly in the development of therapeutic strategies against parasitic infections.

Formula: C₂₇H₄₇N₉O₁₀S₂

InChI: InChI=1S/C27H47N9O10S2/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/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)/t16-,17-,18-,19-/m0/s1

InChI key: InChIKey=LZMSXDHGHZKXJD-VJANTYMQSA-N

SMILES: N(C(CC[C@@H](C(O)=O)N)=O)[C@@H]1C(=O)NCC(=O)NCCCCNCCCNC(=O)CNC(=O)[C@@H](NC(CC[C@@H](C(O)=O)N)=O)CSSC1

Synonyms:

• Glycinamide, L-γ-glutamyl-L-cysteinyl-N-[3-[[4-[[N-(N-L-γ-glutamyl-L-cysteinyl)glycyl]amino]butyl]amino]propyl]-, cyclic (2→3)-disulfide
• Glycinamide, L-γ-glutamyl-L-cysteinyl-N-[3-[[4-[(L-γ-glutamyl-L-cysteinylglycyl)amino]butyl]amino]propyl]-, cyclic (2→2′)-disulfide
• 1,2-Dithia-6,9,13,18,21-pentaazacyclotetracosane, cyclic peptide deriv.
• Trypanothione
• Trypanothione disulfide

Trypanothione

CAS: 96304-42-6

Trypanothione (TS2) was purified from the insect trypanosomatid Crithidia fasciculata and identified as a covalently linked adduct of glutathione and spermidine. TS2 is utilized as a substrate by trypanothione reductase, a unique enzyme found in trypanosomes and leishmanias (Km = 51 µM).

Formula: C₂₇H₄₇N₉O₁₀S₂

Purity: 98.0%

Color and Shape: White Powder

Molecular weight: 721.86

Ref: 01-4014289

Trypanothione

CAS: 96304-42-6

Trypanothione

Molecular weight: 721.85g/mol

Ref: 54-BIBA1013

Trypanothione N1,N8-Bis(glutathionyl)-spermidine disulfide

CAS: 96304-42-6

Trypanothione N1,N8-Bis(glutathionyl)-spermidine disulfide is a reactive oxygen species (ROS) scavenger that is produced by the enzyme glutathione reductase and has been shown to be effective against the protozoan leishmania. The reactivity of this molecule is due to its disulfide bond. This reactive cysteine residue can undergo a redox reaction with ROS, which causes cell lysis and leads to the death of the parasite. Trypanothione N1,N8-Bis(glutathionyl)-spermidine disulfide has been shown to have anti-inflammatory properties in mice, which may be due to its ability to inhibit prostaglandin synthesis. It also has been shown to inhibit the production of proinflammatory cytokines such as tumor necrosis factor alpha (TNF-α).

Formula: C₂₇H₄₇N₉O₁₀S₂

Purity: Min. 95%

Molecular weight: 721.85 g/mol

Ref: 3D-FT110135

Trypanothione

CAS: 96304-42-6

Trypanothione, a bis-glutathionyl derivative present in trypanosomatids, offers protection against oxidative stress [1] [2] [3].

Formula: C₂₇H₄₇N₉O₁₀S₂

Color and Shape: Solid

Molecular weight: 721.85

Ref: TM-T80929