WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H206154
CAS#: 163042-96-4
Description: 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.
Hodoodo Cat#: H206154
Name: Namodenoson
CAS#: 163042-96-4
Chemical Formula: C18H18ClIN6O4
Exact Mass: 544.01
Molecular Weight: 544.731
Elemental Analysis: C, 39.69; H, 3.33; Cl, 6.51; I, 23.30; N, 15.43; O, 11.75
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:
| Biological target: | |
| In vitro activity: | |
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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: | |
| In vitro protocol: | |
| In vivo protocol: |
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.
