Ageladine A . trifluoracetate

CHF 190.00
In stock
AG-CMA-1001-C200200 µgCHF 190.00
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Product Details
Synonyms (4-(4,5-Dibromo-1H-pyrrol-2-yl)-1H-imidazo[4,5-c]-pyridin-2-amine) . TFA
Product Type Chemical
Properties
Formula

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)
Appearance Brown solid.
Solubility Soluble in DMSO or methanol.
Identity Determined by 1H-NMR.
Declaration Manufactured by Marnas Biochemicals.
Other Product Data

Fluorescence specifications:
Excitation 325 - 415nm; maximum at 370nm
Emission 415 - 500nm; maximum at 415nm

Prepare a 1mM stock solution in MeOH or DMSO:
Dissolve 0.425ml methanol into the provided 0.2mg vial of Ageladine A, mix gently until the compound is completely dissolved. The solution should show a homogenous yellow colour. Use fresh preparations or aliquot and freeze immediately. Ageladine A is light sensitive, avoid longer exposition to direct sun light or other intensive light sources. Avoid freeze/thaw cycles of solutions.

InChi Key QAKGJAQGTQLMFN-UHFFFAOYSA-N
Smiles NC1=NC2=C(N=CC=C2N1)C1=CC(Br)=C(Br)N1
Shipping and Handling
Shipping AMBIENT
Short Term Storage +20°C
Long Term Storage +4°C
Handling Advice Protect from light and moisture.
Protect from light when in solution.
Use/Stability 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.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • 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) [2].
  • Highly cell/membrane permeable. Trapped within the cells and acidic organelles through hydrophobic interactions with the inner side of the membranes [2].
  • Barely metabolized and long-term stable, thus slow photobleaching [9].
  • 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].
Product References
  1. Ageladine A: An antiangiogic matrixmetalloproteinase inhibitor from the marine sponge Agelas nakamurai: M. Fujita, et al.; JACS 125, 1570 (2003)
  2. Ageladine A, a pyrrole-imidazole alkaloid from marine sponges, is a pH sensitive membrane permeable dye: U. Bickmeyer, et al.; BBRC 373, 419 (2008)
  3. Synthesis and anticancer activities of ageladine A and structural analogs: Y. Ma, et al.; Bioorg. Med. Chem. Lett. 20, 83 (2010)
  4. Tracking of fast moving neuronal vesicles with ageladine A: U. Bickmeyer, et al.; BBRC 402, 489 (2010)
  5. A one-pot synthesis and biological activity of ageladine A and analogues: S.R. Shengule, et al.; Med. Chem. 54, 2492 (2011)
  6. Synthesis and matrix metalloproteinase-12 inhibitory activity of ageladine A analogs: N. Ando & S. Terashima; Chem. Pharm. Bull. 59, 579 (2011)
  7. 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)
  8. 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)
  9. 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)
  10. Marine-derived angiogenesis inhibitors for cancer therapy: Y.Q. Wang & Z.H. Miao; Mar. Drugs 11, 903 (2013)
  11. 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)
  12. 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)
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