CF-102 | Namodenoson | CAS#163042-96-4 | A3AR agonist

MedKoo Cat#: 206154 | Name: Namodenoson

Description:

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

Namodenoson, also known as 2-Cl-IB-MECA and CF-102, is an orally bioavailable, synthetic, highly selective adenosine A3 receptor (A3AR) agonist with potential antineoplastic activity. Adenosine A3 receptor agonist CF102 selectively binds to and activates the cell surface-expressed A3AR, deregulating Wnt and NF-kB signal transduction pathways downstream, which may result in apoptosis of A3AR-expressing tumor cells. A3AR, a G protein-coupled receptor, is highly expressed on the cell surfaces of various solid tumor cell types, including hepatocellular carcinoma (HCC) cells, and plays an important role in cellular proliferation.

Chemical Structure

Namodenoson

CAS#163042-96-4

Theoretical Analysis

MedKoo Cat#: 206154

Name: Namodenoson

CAS#: 163042-96-4

Chemical Formula: C18H18ClIN6O4

Exact Mass: 544.0123

Molecular Weight: 544.73

Elemental Analysis: C, 39.69; H, 3.33; Cl, 6.51; I, 23.30; N, 15.43; O, 11.75

Price and Availability

Size	Price	Availability
50mg	USD 750.00	2 Weeks
100mg	USD 1,250.00	2 Weeks
200mg	USD 2,250.00	2 Weeks
500mg	USD 3,650.00	2 Weeks
1g	USD 5,450.00	2 Weeks
2g	USD 8,650.00	2 Weeks

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Synonym

CF102; CF-102; CF 102; Cl-IB-MECA; 2-Cl-IB-MECA; Namodenoson; Chloro-IB-MECA;

IUPAC/Chemical Name

(2S,3S,4R,5R)-5-(2-chloro-6-((3-iodobenzyl)amino)-9H-purin-9-yl)-3,4-dihydroxy-N-methyltetrahydrofuran-2-carboxamide

InChi Key

IPSYPUKKXMNCNQ-PFHKOEEOSA-N

InChi Code

InChI=1S/C18H18ClIN6O4/c1-21-16(29)13-11(27)12(28)17(30-13)26-7-23-10-14(24-18(19)25-15(10)26)22-6-8-3-2-4-9(20)5-8/h2-5,7,11-13,17,27-28H,6H2,1H3,(H,21,29)(H,22,24,25)/t11-,12+,13-,17+/m0/s1

SMILES Code

O[C@H]1[C@H](N2C=NC3=C(NCC4=CC=CC(I)=C4)N=C(Cl)N=C23)O[C@H](C(NC)=O)[C@H]1O

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, not in water

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:

Namodenoson (CF-102) is a selective A3 adenosine receptor (A3AR) agonist (Ki=0.33 nM).

In vitro activity:

CF102 at a concentration of 1 and 10 nM induced a linear inhibitory effect on the proliferation of Hep-3B cells (34.5 ± 2.5% and 46.87 ± 3.72%, respectively; Fig. 6). WB analysis showed that Hep-3B cells highly express A3AR which was down-regulated upon CF102 treatment (Fig. 7). Down-regulation of PI3K, PKB/Akt, and NF-κB was also found upon CF102 treatment whereas up-regulation of the pro-apoptotic protein caspase-3 was noted (Fig. 8). Reference: J Cell Physiol. 2011 Sep;226(9):2438-47. https://pubmed.ncbi.nlm.nih.gov/21660967/

In vivo activity:

The hemodynamic effects of the novel, selective adenosine A3 receptor agonist 2-chloro-N6-(3-iodobenzyl)adenosine-5'-N-methylcarboxamide (2-Cl-IB-MECA) were investigated in conscious rats. Intravenous administration of 200 micrograms/kg 2-Cl-IB-MECA resulted in a short-lasting hypotension, which was accompanied by a 50-100-fold increase in plasma histamine concentrations. Reference: Eur J Pharmacol. 1996 Jul 25;308(3):311-4. https://pubmed.ncbi.nlm.nih.gov/8858305/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	18.36
	DMSO	48.7	89.34
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.55

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 544.73 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. Lillo A, Serrano-Marín J, Lillo J, Raïch I, Navarro G, Franco R. Gene regulation in activated microglia by adenosine A3 receptor agonists: a transcriptomics study. Purinergic Signal. 2023 Jan 27. doi: 10.1007/s11302-022-09916-9. Epub ahead of print. PMID: 36703008. 2. Cohen S, Stemmer SM, Zozulya G, Ochaion A, Patoka R, Barer F, Bar-Yehuda S, Rath-Wolfson L, Jacobson KA, Fishman P. CF102 an A3 adenosine receptor agonist mediates anti-tumor and anti-inflammatory effects in the liver. J Cell Physiol. 2011 Sep;226(9):2438-47. doi: 10.1002/jcp.22593. PMID: 21660967; PMCID: PMC3474360. 3. Ohana G, Cohen S, Rath-Wolfson L, Fishman P. A3 adenosine receptor agonist, CF102, protects against hepatic ischemia/reperfusion injury following partial hepatectomy. Mol Med Rep. 2016 Nov;14(5):4335-4341. doi: 10.3892/mmr.2016.5746. Epub 2016 Sep 19. PMID: 27666664. 4. Van Schaick EA, Jacobson KA, Kim HO, IJzerman AP, Danhof M. Hemodynamic effects and histamine release elicited by the selective adenosine A3 receptor agonist 2-Cl-IB-MECA in conscious rats. Eur J Pharmacol. 1996 Jul 25;308(3):311-4. doi: 10.1016/0014-2999(96)00373-1. PMID: 8858305; PMCID: PMC4287249.

In vitro protocol:

In vivo protocol:

1. Ohana G, Cohen S, Rath-Wolfson L, Fishman P. A3 adenosine receptor agonist, CF102, protects against hepatic ischemia/reperfusion injury following partial hepatectomy. Mol Med Rep. 2016 Nov;14(5):4335-4341. doi: 10.3892/mmr.2016.5746. Epub 2016 Sep 19. PMID: 27666664. 2. Van Schaick EA, Jacobson KA, Kim HO, IJzerman AP, Danhof M. Hemodynamic effects and histamine release elicited by the selective adenosine A3 receptor agonist 2-Cl-IB-MECA in conscious rats. Eur J Pharmacol. 1996 Jul 25;308(3):311-4. doi: 10.1016/0014-2999(96)00373-1. PMID: 8858305; PMCID: PMC4287249.

1: Soares AS, Costa VM, Diniz C, Fresco P. The combination of Cl-IB-MECA with paclitaxel: a new anti-metastatic therapeutic strategy for melanoma. Cancer Chemother Pharmacol. 2014 Oct;74(4):847-60. doi: 10.1007/s00280-014-2557-y. Epub 2014 Aug 14. PubMed PMID: 25119183. 2: Soares AS, Costa VM, Diniz C, Fresco P. Potentiation of cytotoxicity of paclitaxel in combination with Cl-IB-MECA in human C32 metastatic melanoma cells: A new possible therapeutic strategy for melanoma. Biomed Pharmacother. 2013 Oct;67(8):777-89. doi: 10.1016/j.biopha.2013.08.003. Epub 2013 Aug 23. PubMed PMID: 24035253. 3: Kim GD, Oh J, Jeong LS, Lee SK. Thio-Cl-IB-MECA, a novel A3 adenosine receptor agonist, suppresses angiogenesis by regulating PI3K/AKT/mTOR and ERK signaling in endothelial cells. Biochem Biophys Res Commun. 2013 Jul 19;437(1):79-86. doi: 10.1016/j.bbrc.2013.06.040. Epub 2013 Jun 21. PubMed PMID: 23791876. 4: Montinaro A, Forte G, Sorrentino R, Luciano A, Palma G, Arra C, Adcock IM, Pinto A, Morello S. Adoptive immunotherapy with Cl-IB-MECA-treated CD8+ T cells reduces melanoma growth in mice. PLoS One. 2012;7(9):e45401. doi: 10.1371/journal.pone.0045401. Epub 2012 Sep 24. PubMed PMID: 23028986; PubMed Central PMCID: PMC3454429. 5: Kim TH, Kim YK, Woo JS. The adenosine A3 receptor agonist Cl-IB-MECA induces cell death through Ca2⁺/ROS-dependent down regulation of ERK and Akt in A172 human glioma cells. Neurochem Res. 2012 Dec;37(12):2667-77. doi: 10.1007/s11064-012-0855-5. Epub 2012 Aug 10. PubMed PMID: 22878643. 6: Lee HS, Chung HJ, Lee HW, Jeong LS, Lee SK. Suppression of inflammation response by a novel A3 adenosine receptor agonist thio-Cl-IB-MECA through inhibition of Akt and NF-κB signaling. Immunobiology. 2011 Sep;216(9):997-1003. doi: 10.1016/j.imbio.2011.03.008. Epub 2011 Apr 7. PubMed PMID: 21514967. 7: Morello S, Sorrentino R, Montinaro A, Luciano A, Maiolino P, Ngkelo A, Arra C, Adcock IM, Pinto A. NK1.1 cells and CD8 T cells mediate the antitumor activity of Cl-IB-MECA in a mouse melanoma model. Neoplasia. 2011 Apr;13(4):365-73. PubMed PMID: 21472141; PubMed Central PMCID: PMC3071085. 8: Forte G, Sorrentino R, Montinaro A, Pinto A, Morello S. Cl-IB-MECA enhances TNF-α release in peritoneal macrophages stimulated with LPS. Cytokine. 2011 May;54(2):161-6. doi: 10.1016/j.cyto.2011.02.002. Epub 2011 Feb 26. PubMed PMID: 21354814. 9: Kim H, Kang JW, Lee S, Choi WJ, Jeong LS, Yang Y, Hong JT, Yoon do Y. A3 adenosine receptor antagonist, truncated Thio-Cl-IB-MECA, induces apoptosis in T24 human bladder cancer cells. Anticancer Res. 2010 Jul;30(7):2823-30. PubMed PMID: 20683018. 10: Morello S, Sorrentino R, Porta A, Forte G, Popolo A, Petrella A, Pinto A. Cl-IB-MECA enhances TRAIL-induced apoptosis via the modulation of NF-kappaB signalling pathway in thyroid cancer cells. J Cell Physiol. 2009 Nov;221(2):378-86. doi: 10.1002/jcp.21863. PubMed PMID: 19562684.