Gardiquimod diTFA | CAS#1159840-61-5

MedKoo Cat#: 330135 | Name: Gardiquimod diTFA

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Gardiquimod diTFA

CAS#1159840-61-5 (2TFA)

Theoretical Analysis

MedKoo Cat#: 330135

Name: Gardiquimod diTFA

CAS#: 1159840-61-5 (2TFA)

Chemical Formula: C19H24F3N5O3

Exact Mass: 0.0000

Molecular Weight: 427.43

Elemental Analysis: C, 53.39; H, 5.66; F, 13.33; N, 16.39; O, 11.23

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 850.00	2 Weeks
200mg	USD 1,450.00	2 Weeks
500mg	USD 2,850.00	2 Weeks

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Related CAS #

1020412-43-4 (free base) 2956183-81-4 (HCl) 1159840-61-5 (2TFA)

Synonym

Gardiquimod diTFA salt; Gardiquimod trifluoroacetate; Gardiquimod (diTFA); Gardiquimod TFA; Gardiquimod bis-TFA salt; Gardiquimodtrifluoroacetate; gardiquimod; bis(trifluoroacetic acid)

IUPAC/Chemical Name

1-(4-amino-2-((ethylamino)methyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol bis(2,2,2-trifluoroacetate)

InChi Key

XFQPQSJDMJVOBN-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H23N5O.2C2HF3O2/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;2*3-2(4,5)1(6)7/h5-8,19,23H,4,9-10H2,1-3H3,(H2,18,20);2*(H,6,7)

SMILES Code

CCNCC1=NC2=C(C3=CC=CC=C3N=C2N)N1CC(C)(O)C.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

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.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Gardiquimod diTFA, an imidazoquinoline analog, is a TLR7/8 agonist.

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	116.98
	Water	25.0	58.49

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 427.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Buitendijk M, Eszterhas SK, Howell AL. Gardiquimod: a Toll-like receptor-7 agonist that inhibits HIV type 1 infection of human macrophages and activated T cells. AIDS Res Hum Retroviruses. 2013 Jun;29(6):907-18. doi: 10.1089/aid.2012.0313. Epub 2013 Feb 5. PMID: 23316755; PMCID: PMC3653394. 2. Zhou Z, Yu X, Zhang J, Tian Z, Zhang C. TLR7/8 agonists promote NK-DC cross-talk to enhance NK cell anti-tumor effects in hepatocellular carcinoma. Cancer Lett. 2015 Dec 28;369(2):298-306. doi: 10.1016/j.canlet.2015.09.017. Epub 2015 Oct 9. PMID: 26433159. 3. Cho KHT, Fraser M, Xu B, Dean JM, Gunn AJ, Bennet L. Induction of Tertiary Phase Epileptiform Discharges after Postasphyxial Infusion of a Toll-Like Receptor 7 Agonist in Preterm Fetal Sheep. Int J Mol Sci. 2021 Jun 19;22(12):6593. doi: 10.3390/ijms22126593. PMID: 34205464; PMCID: PMC8234830. 4. Leung PY, Stevens SL, Packard AE, Lessov NS, Yang T, Conrad VK, van den Dungen NN, Simon RP, Stenzel-Poore MP. Tolllike receptor 7 preconditioning induces robust neuroprotection against stroke by a novel type I interferon-mediated mechanism. Stroke. 2012 May;43(5):1383-9. doi: 10.1161/STROKEAHA.111.641522. Epub 2012 Mar 8. PMID: 22403050; PMCID: PMC3943206.

In vitro protocol:

In vivo protocol:

1. Cho KHT, Fraser M, Xu B, Dean JM, Gunn AJ, Bennet L. Induction of Tertiary Phase Epileptiform Discharges after Postasphyxial Infusion of a Toll-Like Receptor 7 Agonist in Preterm Fetal Sheep. Int J Mol Sci. 2021 Jun 19;22(12):6593. doi: 10.3390/ijms22126593. PMID: 34205464; PMCID: PMC8234830. 2. Leung PY, Stevens SL, Packard AE, Lessov NS, Yang T, Conrad VK, van den Dungen NN, Simon RP, Stenzel-Poore MP. Tolllike receptor 7 preconditioning induces robust neuroprotection against stroke by a novel type I interferon-mediated mechanism. Stroke. 2012 May;43(5):1383-9. doi: 10.1161/STROKEAHA.111.641522. Epub 2012 Mar 8. PMID: 22403050; PMCID: PMC3943206.

1: Guo S, Zhang Y, Wang Z, Yu Y, Wang G. Intraperitoneal gardiquimod protects against hepatotoxicity through inhibition of oxidative stress and inflammation in mice with sepsis. J Biochem Mol Toxicol. 2017 Aug;31(8). doi: 10.1002/jbt.21923. Epub 2017 Apr 19. PubMed PMID: 28422377. 2: Jia B, Luo X, Cheng FW, Li L, Hu DJ, Wang F, Zhang SQ. Gardiquimod inhibits the expression of calcium-induced differentiation markers in HaCaT cells. Mol Biol Rep. 2013 Nov;40(11):6363-9. doi: 10.1007/s11033-013-2750-9. Epub 2013 Sep 22. PubMed PMID: 24057248. 3: Buitendijk M, Eszterhas SK, Howell AL. Gardiquimod: a Toll-like receptor-7 agonist that inhibits HIV type 1 infection of human macrophages and activated T cells. AIDS Res Hum Retroviruses. 2013 Jun;29(6):907-18. doi: 10.1089/AID.2012.0313. Epub 2013 Feb 5. PubMed PMID: 23316755; PubMed Central PMCID: PMC3653394. 4: Ma F, Zhang J, Zhang J, Zhang C. The TLR7 agonists imiquimod and gardiquimod improve DC-based immunotherapy for melanoma in mice. Cell Mol Immunol. 2010 Sep;7(5):381-8. doi: 10.1038/cmi.2010.30. Epub 2010 Jun 14. PubMed PMID: 20543857; PubMed Central PMCID: PMC4002679.