Toyocamycin

- Overview
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    Background
    
    Toyocamycin is an inhibitor of phosphatidylinositol kinase. It is known as an antifungal antibiotic. [1]
    Phosphatidylinositol kinase is one of the important enzymes that take part in the regulation of the pathway of phosphatidylinositol turnover. Phosphatidylinositol turnover is studied to be involved in the cellular response to mitogens and transformation.[1]
    Toyocamycin can suppress thapsigargin-, tunicamycin- and 2-deoxyglucose-induced XBP1 mRNA splicing in HeLa cells. This suppression doesn’t affect the activating of transcription factor 6 (ATF6) and PKR-like ER kinase (PERK)’s activation. Toyocamycin prevents IRE1a-induced XBP1 mRNA cleavage in vitro. [2]
    In mammalian cells, toyocamycin inhibits RNA synthesis. Toyocamycin induces apoptosis of MM cells including bortezomib-resistant cells at nanomolar levels in a dose-dependent manner. It also inhibited growth of xenografts in an in vivo model of human multiple myeloma. It is also a lead compound for developing anti-MM therapy and XBP1 as an appropriate molecular target for anti-multiple myeloma therapy.[2]
    
    [1]Nishioka H, Sawa T, etal. , Inhibition of phosphatidylinositol kinase by toyocamycin. J Antibiot (Tokyo). 1990 Dec;43(12):1586-9.
    [2]Ri M, Tashiro E, Oikawa D, etal. , Identification of Toyocamycin,an agent cytotoxic for multiple myeloma cells, as a potent inhibitor of ER stress-induced XBP1 mRNA splicing. Blood Cancer J. 2012 Jul;2(7):e79.
- Properties
  - Categories
    
    Adenosine analog, antitumor antibiotic
    
    Alternative Name
    
    4-amino-7-((2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
    
    CAS Number
    
    606-58-6
    
    Molecular Formula
    
    C12H13N5O4
    
    Molecular Weight
    
    291.26
    
    Appearance
    
    A crystalline solid
    
    Purity
    
    98.00%
    
    Solubility
    
    ≥77 mg/mL in DMSO; ≥1.16 mg/mL in EtOH with gentle warming and ultrasonic; ≥1.34 mg/mL in H2O with gentle warming and ultrasonic
    
    Storage
    
    Store at -20°C
    
    SMILES
    
    O[[email protected]]1[[email protected]@H](N2C3=NC=NC(N)=C3C(C#N)=C2)O[[email protected]@H](CO)[[email protected]@H]1O
    
    * For Research Use Only
- Reference
  - 1. Mudassar N. Mughal, Qing Ye, et al. "First Evidence of Function for Schistosoma japonicumriok-1 and RIOK-1." Pathogens. 2021 Jul 8;10(7):862. PMID:34358012

Documents

COA (Certificate Of Analysis)

MSDS (Material Safety Data Sheet)

Datasheet

Toyocamycin

Background

Documents

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