All Photos(1)
Synonym(s):
N-Acetyl-L-threonyl-L-α-aspartyl-N5-(2-fluoro-1-iminoethyl)-L-ornithinamide trifluoroacetate salt, Thr-Asp-F-amidine trifluoroacetate salt
Empirical Formula (Hill Notation):
C17H29FN6O7 · xC2HF3O2
Molecular Weight:
448.45 (free base basis)
UNSPSC Code:
12352200
NACRES:
NA.77
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Quality Level
Assay
≥98% (HPLC)
form
powder
storage condition
desiccated
color
white to beige
solubility
H2O: 10 mg/mL, clear
shipped in
dry ice
storage temp.
−70°C
General description
TDFA trifluoroacetate salt or tripeptide F-amidine analog is a derivative synthesized to increase the selectivity, bioavailability and potency of Cl-amidine, which is a member of protein arginine deiminases (PADs) compounds.
Biochem/physiol Actions
TDFA (Thr-Asp-F-amidine) is a selective inhibitor of peptidyl arginine deiminase 4 (protein arginine deiminase 4, PAD4 or PADI4), a transcriptional coregulator that catalyzes the calcium-dependent conversion of specific arginine residues in proteins to citrulline, a process called citrullination. PAD4 is upregulated in cancer and inflammatory diseases, and may be involved in rheumatoid arthritis onset and progression. It has recently been found to be involved in the regulation of pluripotency: important for stem-cell gene activation, induced pluripotent stem (iPS) cell reprogramming, and maintenance of pluripotent cells in the early mouse embryo. TDFA has an IC50 value of 2.3 μM and is ≥15-fold selective for PAD4 versus PAD1 and ≥50-fold selective versus PADs 2 and 3.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Certificates of Analysis (COA)
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Design, synthesis, and biological evaluation of tetrazole analogs of Cl-amidine as protein arginine deiminase inhibitors.
Subramanian V
Journal of Medicinal Chemistry, 58(3), 1337-1344 (2015)
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