Ageladine A . trifluoracetate
|Synonyms||(4-(4,5-Dibromo-1H-pyrrol-2-yl)-1H-imidazo[4,5-c]-pyridin-2-amine) . TFA|
C10H7Br2N5 . C2HF3O2
|MW||357.0 . 114.0|
|CAS||950766-21-9 | 643020-13-7 (free base)|
|Source/Host Chemicals||Synthetic. Originally isolated from Agelas nakamurai.|
|Purity Chemicals||≥98% (NMR)|
|Solubility||Soluble in DMSO or methanol.|
|Identity||Determined by 1H-NMR.|
|Declaration||Manufactured by Marnas Biochemicals.|
|Other Product Data||
|Shipping and Handling|
|Short Term Storage||+20°C|
|Long Term Storage||+4°C|
Protect from light and moisture.
Protect from light when in solution.
Stable for at least 1 year after receipt when stored at +4°C.
Stock solutions are stable for at least 3 months when stored at -20°C.
|Product Specification Sheet|
- Non-toxic, pH-sensitive fluorescent dye (blue-green range) for live imaging of pH alteration in acidic organelles, vesicles, cells, tissue and even small whole animals over several days without side effects [2,4,5,7-9].
- Stronger fluorescent intensity under acidic conditions and barely detectable in alkaline solutions (wide range from pH 4 to pH 8) .
- Highly cell/membrane permeable. Trapped within the cells and acidic organelles through hydrophobic interactions with the inner side of the membranes .
- Barely metabolized and long-term stable, thus slow photobleaching .
- Angiogenesis inhibitor [1,3,6].
- Inhibitor of matrix metalloproteinases MMP-1,-2,-8,-9,-12,-13 [1, 3-6].
- TYK2, DYRK2,Dyrk1A, YSK4 and RPS6KA1/2 inhibitor [3,5,6].
- Ageladine A: An antiangiogic matrixmetalloproteinase inhibitor from the marine sponge Agelas nakamurai: M. Fujita, et al.; JACS 125, 1570 (2003)
- Ageladine A, a pyrrole-imidazole alkaloid from marine sponges, is a pH sensitive membrane permeable dye: U. Bickmeyer, et al.; BBRC 373, 419 (2008)
- Synthesis and anticancer activities of ageladine A and structural analogs: Y. Ma, et al.; Bioorg. Med. Chem. Lett. 20, 83 (2010)
- Tracking of fast moving neuronal vesicles with ageladine A: U. Bickmeyer, et al.; BBRC 402, 489 (2010)
- A one-pot synthesis and biological activity of ageladine A and analogues: S.R. Shengule, et al.; Med. Chem. 54, 2492 (2011)
- Synthesis and matrix metalloproteinase-12 inhibitory activity of ageladine A analogs: N. Ando & S. Terashima; Chem. Pharm. Bull. 59, 579 (2011)
- The alkaloid Ageladine A, originally isolated from marine sponges, used for pH-sensitive imaging of transparent marine animals: U. Bickmeyer; Mar. Drugs 10, 223 (2012)
- Incorporated nematocysts in Aeolidiella stephanieae (Gastropoda, Opisthobranchia, Aeolidoidea) mature by acidification shown by the pH sensitive fluorescing alkaloid Ageladine A: D. Obermann, et al.; Toxicon 60, 1108 (2012)
- Reporter dyes demonstrate functional expression of multidrug resistance proteins in the marine flatworm Macrostomum lignano: The sponge-derived dye ageladine A is not a substrate of these transporters: K. Tietje, et al.; Mar. Drugs 11, 3951 (2013)
- Marine-derived angiogenesis inhibitors for cancer therapy: Y.Q. Wang & Z.H. Miao; Mar. Drugs 11, 903 (2013)
- The physiological response of the marine platyhelminth Macrostomum lignano to different environmental oxygen concentrations: G.A. Rivera-Ingraham, et al.; J. Exp. Biol. 216, 2741 (2013)
- The chemically synthesized ageladine A-derivative LysoGlow84 stains lysosomes in viable mammalian brain cells and specific structures in the marine flatworm Macrostomum lignano: T. Mordhorst, et al.; Mar. Drugs 13, 920 (2015)