WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 584460
CAS#: 122970-40-5 (free base)
Description: Isatoribine (also known as immunosine, or 7-thia-8-oxoguanosine) is a novel guanosine analogue showing immunostimulatory activity both in vivo and in vitro. This compound acts on different components of the immune system including B cells, natural killer (NK) cells and antigen-presenting cells (APC). It was found that immunosine significantly stimulates proliferation of T cells. The effect was dose-dependent and also depended on concentrations of specific stimulators. Maximal stimulation was seen using 250 microM immunosine.
MedKoo Cat#: 584460
Name: Isatoribine free base
CAS#: 122970-40-5 (free base)
Chemical Formula: C10H12N4O6S
Exact Mass: 316.0478
Molecular Weight: 316.288
Elemental Analysis: C, 37.97; H, 3.82; N, 17.71; O, 30.35; S, 10.14
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Synonym: ANA245; ANA-245; ANA 245; Immusine; Isatoribine; Isatoribine monohydrate; D04619; 7-thia-8-oxoguanosine.
IUPAC/Chemical Name: Thiazolo(4,5-d)pyrimidine-2,7(3H,4H)-dione, 5-amino-3-beta-D-ribofuranosyl-
InChi Key: TZYVRXZQAWPIAB-FCLHUMLKSA-N
InChi Code: InChI=1S/C10H12N4O6S/c11-9-12-6-5(7(18)13-9)21-10(19)14(6)8-4(17)3(16)2(1-15)20-8/h2-4,8,15-17H,1H2,(H3,11,12,13,18)/t2-,3-,4-,8-/m1/s1
SMILES Code: O=C(N1[C@H]2[C@@H]([C@@H]([C@@H](CO)O2)O)O)SC3=C1NC(N)=NC3=O
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
The following data is based on the product molecular weight 316.288 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|
1: Xiang AX, Webber SE, Kerr BM, Rueden EJ, Lennox JR, Haley GJ, Wang T, Ng JS, Herbert MR, Clark DL, Banh VN, Li W, Fletcher SP, Steffy KR, Bartkowski DM, Kirkovsky LI, Bauman LA, Averett DR. Discovery of ANA975: an oral prodrug of the TLR-7 agonist isatoribine. Nucleosides Nucleotides Nucleic Acids. 2007;26(6-7):635-40. PubMed PMID: 18066870.
2: Horsmans Y, Berg T, Desager JP, Mueller T, Schott E, Fletcher SP, Steffy KR, Bauman LA, Kerr BM, Averett DR. Isatoribine, an agonist of TLR7, reduces plasma virus concentration in chronic hepatitis C infection. Hepatology. 2005 Sep;42(3):724-31. PubMed PMID: 16116638.
3: Kini GD, Anderson JD, Sanghvi YS, Lewis AF, Smee DF, Revankar GR, Robins RK, Cottam HB. Synthesis and antiviral activity of certain guanosine analogues in the thiazolo[4,5-d]pyrimidine ring system. J Med Chem. 1991 Oct;34(10):3006-10. PubMed PMID: 1656042.
4: Lewis AF, Drach JC, Fennewald SM, Huffman JH, Ptak RG, Sommadossi JP, Revankar GR, Rando RF. Inhibition of human cytomegalovirus in culture by alkenyl guanine analogs of the thiazolo[4,5-d]pyrimidine ring system. Antimicrob Agents Chemother. 1994 Dec;38(12):2889-95. PubMed PMID: 7695278; PubMed Central PMCID: PMC188302.
5: Sharma BS, Balazs L, Jin A, Wang JC, Jolley WB, Robins RK. Potentiation of the efficacy of murine L1210 leukemia vaccine by a novel immunostimulator 7-thia-8-oxoguanosine: increased survival after immunization with vaccine plus 7-thia-8-oxoguanosine. Cancer Immunol Immunother. 1991;33(2):109-14. PubMed PMID: 2036658.
6: Smee DF, Alaghamandan HA, Cottam HB, Sharma BS, Jolley WB, Robins RK. Broad-spectrum in vivo antiviral activity of 7-thia-8-oxoguanosine, a novel immunopotentiating agent. Antimicrob Agents Chemother. 1989 Sep;33(9):1487-92. PubMed PMID: 2817849; PubMed Central PMCID: PMC172688.
7: Sharma BS, Mhaskar S, Balazs L, Siaw M. Immunomodulatory activity of a novel nucleoside, 7-thia-8-oxoguanosine: I. Activation of natural killer cells in mice. Immunopharmacol Immunotoxicol. 1992;14(1-2):1-19. PubMed PMID: 1597650.
8: Dzopalic T, Dragicevic A, Bozic B, Rajkovic I, Colic M. Dose-dependent response of dendritic cells to 7-thia-8-oxo-guanosine and its modulation by polyinosinic:polycytidylic acid. Exp Biol Med (Maywood). 2012 Jul;237(7):784-92. doi: 10.1258/ebm.2012.011409. Epub 2012 Aug 2. PubMed PMID: 22859738.
9: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Nov;27(9):665-77. PubMed PMID: 16357953.
10: Smee DF, Alaghamandan HA, Jin A, Sharma BS, Jolley WB. Roles of interferon and natural killer cells in the antiviral activity of 7-thia-8-oxoguanosine against Semliki Forest virus infections in mice. Antiviral Res. 1990 Feb;13(2):91-102. PubMed PMID: 1693058.
11: Sharma BS, Balazs L, Jin A, Jolley WB, Robins RK. Successful immunotherapy of murine melanoma metastases with 7-thia-8-oxoguanosine. Clin Exp Metastasis. 1991 Sep-Oct;9(5):429-39. PubMed PMID: 1914279.
12: Smee DF, Alaghamandan HA, Cottam HB, Jolley WB, Robins RK. Antiviral activity of the novel immune modulator 7-thia-8-oxoguanosine. J Biol Response Mod. 1990 Feb;9(1):24-32. PubMed PMID: 2156954.
13: Fletcher S, Steffy K, Averett D. Masked oral prodrugs of toll-like receptor 7 agonists: a new approach for the treatment of infectious disease. Curr Opin Investig Drugs. 2006 Aug;7(8):702-8. Review. PubMed PMID: 16955681.
14: Parandoosh Z, Ojo-Amaize E, Robins RK, Jolley WB, Rubalcava B. Stimulation of phosphoinositide signaling pathway in murine B lymphocytes by a novel guanosine analog, 7-thia-8-oxoguanosine. Biochem Biophys Res Commun. 1989 Sep 29;163(3):1306-11. PubMed PMID: 2551285.
15: Smee DF, Huffman JH, Gessaman AC, Huggins JW, Sidwell RW. Prophylactic and therapeutic activities of 7-thia-8-oxoguanosine against Punta Toro virus infections in mice. Antiviral Res. 1991 Mar-Apr;15(3):229-39. PubMed PMID: 1716090.
16: Black PL, McKinnon KM, Wooden SL, Ussery MA. Antiviral activity of biological response modifiers in a murine model of AIDS. Requirement for augmentation of natural killer cell activity and synergy with oral AZT. Int J Immunopharmacol. 1996 Nov;18(11):633-50. PubMed PMID: 9089007.
17: Colić M, Gasić S, Vasilijić S, Pejanović V, Jandrić D, Medić-Mijacević L, Rakić L. A nucleoside analogue, 7-thia-8-oxoguanosine stimulates proliferation of thymocytes in vitro. Immunol Lett. 1999 Sep 1;69(3):293-300. PubMed PMID: 10528791.
18: Colic M, Vucevic D, Vasilijic S, Popovic L, Pejanovic V, Jandric D, Medic-Mijacevic L, Rakic L. Proliferation of spleen cells in culture stimulated by 7-thia-8-oxoguanosine: evidence that both B- and T-cells are the targets of its action. Methods Find Exp Clin Pharmacol. 1999 Nov;21(9):583-90. PubMed PMID: 10669901.
19: Colić M, Gasić S, Vucević D, Pavicić L, Popović P, Jandrić D, Medić-Mijacević L, Rakić L. Modulatory effect of 7-thia-8-oxoguanosine on proliferation of rat thymocytes in vitro stimulated with concanavalin A. Int J Immunopharmacol. 2000 Mar;22(3):203-12. PubMed PMID: 10685003.
20: Colić M, Jandrić D, Gasić S, Vucević D, Popović P, Medić-Mijacević L, Rakić L. Immunosine (7-thia-8-oxoguanosine) acts as a cofactor for proliferation of T cells. Fundam Clin Pharmacol. 2000 May-Jun;14(3):209-17. PubMed PMID: 15602797.