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ProductsBack/Ageladine A . TFA [643020-13-7]
Chemical Structure
Chemical Structure
Chemical Structure

Ageladine A . TFA [643020-13-7]

Research Use Only
AG-CMA-1001
AdipoGen Life Sciences
CAS Number643020-13-7
DownloadMSDS
Product group Chemicals
Estimated Purity>98%
Molecular Weight357.0 . 114.0
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Ageladine A . TFA
  • Delivery Days Customer
    10
  • CAS Number
    643020-13-7
  • Certification
    Research Use Only
  • Estimated Purity
    >98%
  • Molecular Formula
    C10H7Br2N5 . C2HF3O2
  • Molecular Weight
    357.0 . 114.0
  • Scientific Description
    Chemical. CAS: 950766-21-9 - 643020-13-7 (free base). Formula: C10H7Br2N5 . C2HF3O2. MW: 357.0 . 114.0. Synthetic. Originally isolated from Agelas nakamurai. 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. 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. Inhibitor of matrix metalloproteinases MMP-1,-2,-8,-9,-12,-13. TYK2, DYRK2,Dyrk1A, YSK4 and RPS6KA1/2 inhibitor. - 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].
  • SMILES
    NC1=NC2=C(N=CC=C2N1)C1=CC(Br)=C(Br)N1
  • Storage Instruction
    -20°C,2°C to 8°C
  • UNSPSC
    41116134

References

  • Ageladine A: An antigiogenetic 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)