| Identification | Back Directory | [Name]
Tropodithietic acid [TDA] | [CAS]
750590-18-2 | [Synonyms]
Tropodithietic acid
Tropodithietic acid [TDA]
from Phaeobacter inhibens
3-Oxo-8,9-dithiabicyclo[5.2.0]nona-1,4,6-triene-2-carboxylic acid
8,9-Dithiabicyclo[5.2.0]nona-1,4,6-triene-2-carboxylic acid, 3-oxo- | [Molecular Formula]
C8H4O3S2 | [MDL Number]
MFCD24485342 | [MOL File]
750590-18-2.mol | [Molecular Weight]
212.25 |
| Chemical Properties | Back Directory | [storage temp. ]
-20°C | [solubility ]
DMSO: soluble5mg/mL, clear (warmed) | [form ]
powder | [color ]
faint yellow to dark yellow | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month. |
| Hazard Information | Back Directory | [Description]
Tropodithietic acid (750590-18-2) displays potent broad-spectrum anticancer activity.1 Displays cytotoxic effects on mammalian cell lines (neuronal N2a cells and OLN-93 cells as model systems for nerve cells and glia) acting via disruption of mitochondrial membrane potential, activation of ERK1/2 and induction of HSP32/HO-1 (considered as a sensor of oxidative stress).2 A broad-spectrum antibiotic agent produced by marine bacteria which does not appear to induce resistance after long-term exposure.3 | [Uses]
Tropodithietic Acid (cas# 750590-18-2) is a compound useful in organic synthesis. | [Definition]
ChEBI: Tropodithietic acid is a monocarboxylic acid that is 8,9-dithiabicyclo[5.2.0]nona-1,3,6-triene substituted by a carboxy group at position 2 and an oxo group at position 3. It is a broad spectrum antibiotic produced by the marine bacterium Phaeobacter inhibens that also acts as a signalling molecule at lower concentrations. It has a role as a toxin, a signalling molecule, a marine metabolite, an antibacterial agent and a bacterial metabolite. It is an organic disulfide, a cyclic ketone, an organosulfur heterocyclic compound, an organic heterobicyclic compound and a monocarboxylic acid. It is a tautomer of a thiotropocin. | [storage]
Store at -20°C | [References]
1) Wilson et al. (2016), Mode of action and resistance studies unveil new roles for tropodithietic acid as an anticancer agent and the γ-glutamyl cycle as a proton sink; Proc. Natl. Acad. Sci. USA, 113 1630
2) Wichmann et al. (2015), Cytotoxic Effects of Tropodithietic Acid on Mammalian Clonal Cell Lines of Neuronal and Glial Origin; Mar. Drugs, 13 7113
3) Rasmussen et al. (2016), Vibro anguillarum is Genetically and Phenotypically Unaffected by Long-Term Continuous Exposure to the Antibacterial Compound Tropodithietic Acid; Appl. Environ. Microbiol., 82 4802 |
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| Company Name: |
Energy Chemical
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021-58432009 400-005-6266 |
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http://www.energy-chemical.com |
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