Gardiquimod TFA

• CAS: 1159840-61-5
• Catalog Number: ACM1159840615
• Category: Others
• Molecular Weight: 427.43
• Molecular Formula: C19H24F3N5O3
• Description: Gardiquimod is a chemical compound which acts selectively at both mouse and human forms of toll-like receptor 7 (TLR7). It functions as an immune response modifier. The core structure is 1H-imidazo[4,5-c]quinoline, as found in related drugs such as imiquimod and resiquimod. It is structurally very similar to resiquimod differing only by an oxygen for nitrogen switch.
• Synonyms: Gardiquimod TFA salt; Gardiquimod
• IUPAC Name: 1-(4-amino-2-((ethylamino)methyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol 2,2,2-trifluoroacetate
• Canonical SMILES: CC(O)(C)CN1C(CNCC)=NC2=C1C3=CC=CC=C3N=C2N.O=C(O)C(F)(F)F
• InChI: InChI=1S/C17H23N5O.C2HF3O2/c1-4-19-9-13-21-14-15(22(13)10-17(2,3)23)11-7-5-6-8-12(11)20-16(14)18;3-2(4,5)1(6)7/h5-8,19,23H,4,9-10H2,1-3H3,(H2,18,20);(H,6,7)
• InChI Key: POTWNBLXWPBSSG-UHFFFAOYSA-N
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Shelf Life: >2 years if stored properly
• Storage: Dry, dark and at 0-4 °C for short term (days to weeks) or -20 °C for long term (months to years).
• Alternative CAS: 1159840-61-5 (TFA); 1020412-43-4 (free base)
• Biological Target: Gardiquimod diTFA, an imidazoquinoline analog, is a TLR7/8 agonist.
• Drug Formulation: This drug may be formulated in DMSO
• Elemental Analysis: C, 53.39; H, 5.66; F, 13.33; N, 16.39; O, 11.23
• Exact Mass: 427.1831
• HS Tariff Code: 2934.99.9001
• In Vitro Activity: Treatment of macrophages with gardiquimod on day 5 of culture, followed by infection with HIV-1Ba-L on day 8, significantly reduced levels of HIV-1 DNA in the cells (p≤0.001) at all gardiquimod concentrations tested compared to untreated controls, as determined on day 4 postinfection (Fig. 1).; Reference: AIDS Res Hum Retroviruses. 2013 Jun;29(6):907-18. https://pubmed.ncbi.nlm.nih.gov/23316755/
• In Vivo Activity: GDQ (gardiquimod) infusion was associated with sustained moderate hypertension that resolved after 72 h recovery. Electrophysiologically, GDQ infusion was associated with reduced number and burden of postasphyxial seizures in preterm fetal sheep in the first 18 h of recovery (p < 0.05). Subsequently, GDQ was associated with induction of slow rhythmic epileptiform discharges (EDs) from 72 to 96 h of recovery (p < 0.05 vs asphyxia + vehicle). The total burden of EDs was associated with reduced numbers of neurons in the caudate nucleus (r2 = 0.61, p < 0.05) and CA1/2 hippocampal region (r2 = 0.66, p < 0.05). These data demonstrate that TLR7 activation by GDQ modulated blood pressure and suppressed seizures in the early phase of postasphyxial recovery, with subsequent prolonged induction of epileptiform activity.; Reference: Int J Mol Sci. 2021 Jun 19;22(12):6593. https://pubmed.ncbi.nlm.nih.gov/34205464/
• Shipping: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
• Stock Solution Storage: 0-4 °C for short term (days to weeks), or -20 °C for long term (months).