Oxanosine
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MedKoo CAT#: 464785

CAS#: 80394-72-5

Description: Oxanosine is an analog of guanosine that has been found in S. capreolus and has diverse biological activities, including antibacterial, antiviral, and anticancer properties. It is active against a variety of bacteria, including S. flexneri, P. mirabilis, and E. coli (MICs = 6.25, 12.5, 25 µg/ml, respectively, on peptone, but not nutrient, agar). Oxanosine inhibits replication of the HIV-1 strain IIIb in infected CEM and U937, but not H9, cells (EC50s = 7, 27, and >500 µg/ml, respectively). It also inhibits the growth of HeLa human cervical cancer cells (IC50 = 32 µg/ml) and reduces tumor growth in a murine L1210 lymphocytic leukemia model.

Chemical Structure

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Oxanosine
CAS# 80394-72-5
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 464785
Name: Oxanosine
CAS#: 80394-72-5
Chemical Formula: C10H12N4O6
Exact Mass: 284.08
Molecular Weight: 284.228
Elemental Analysis: C, 42.26; H, 4.26; N, 19.71; O, 33.77

Price and Availability

Size Price Availability Quantity
10mg USD -2 2 Weeks
25mg USD -2 2 Weeks
50mg USD -2 2 Weeks
100mg USD -2 2 Weeks
200mg USD -2 2 Weeks
500mg USD -2 2 Weeks
2g USD -2 2 Weeks
5g USD -2 2 Weeks
1mg USD 650 2 Weeks
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Synonym: Oxanosine; NSC 359452; NSC359452; NSC-359452;

IUPAC/Chemical Name: 5-amino-3-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)imidazo[4,5-d][1,3]oxazin-7(3H)-one

InChi Key: PWVUOVPUCZNICU-ZIYNGMLESA-N

InChi Code: InChI=1S/C10H12N4O6/c11-10-13-7-4(9(18)20-10)12-2-14(7)8-6(17)5(16)3(1-15)19-8/h2-3,5-6,8,15-17H,1H2,(H2,11,13)/t3-,5-,6-,8-/m1/s1

SMILES Code: OC[C@H]1O[C@@]([H])(N2C=NC3=C2N=C(OC3=O)N)[C@H](O)[C@@H]1O

Appearance: Solid powder

Purity: >90% (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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:
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Biological target: Oxanosine is an analog of guanosine that has been found in S. capreolus and has diverse biological activities, including antibacterial, antiviral, and anticancer properties.
In vitro activity: This study demonstrates that oxanosine monophosphate (OxMP) is a potent reversible competitive inhibitor of IMPDH. UV spectroscopy and X-ray crystallography indicate that OxMP forms a ring-opened covalent adduct with the active site Cys (E-OxMP*). Unlike the covalent intermediate of the normal catalytic reaction, E-OxMP* does not hydrolyze, but instead recyclizes to OxMP. IMPDH inhibitors block proliferation and can induce apoptosis, so the inhibition of IMPDH by OxMP presents another potential mechanism for RNS toxicity. Reference: Chem Res Toxicol. 2019 Mar 18;32(3):456-466. https://pubmed.ncbi.nlm.nih.gov/30746940/
In vivo activity: Oxanosine inhibited the growth of HeLa cells in vitro (IC50 32 mcg/ml) and suppressed the growth of L-1210 leukemia in mice. The primary action of oxanosine appears to be inhibition of GMP-synthetase. Intravenous injection of 4 mg of oxanosine to mice does not show any toxic sign. Reference: Nucleic Acids Symp Ser. 1981;(10):55-8. https://pubmed.ncbi.nlm.nih.gov/7031611/

Preparing Stock Solutions

The following data is based on the product molecular weight 284.23 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.

Recalculate based on batch purity %
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. Yu R, Kim Y, Maltseva N, Braunstein P, Joachimiak A, Hedstrom L. Oxanosine Monophosphate Is a Covalent Inhibitor of Inosine 5'-Monophosphate Dehydrogenase. Chem Res Toxicol. 2019 Mar 18;32(3):456-466. doi: 10.1021/acs.chemrestox.8b00342. Epub 2019 Feb 25. PMID: 30746940; PMCID: PMC6467267. 2. Itoh O, Kuroiwa S, Atsumi S, Umezawa K, Takeuchi T, Hori M. Induction by the guanosine analogue oxanosine of reversion toward the normal phenotype of K-ras-transformed rat kidney cells. Cancer Res. 1989 Feb 15;49(4):996-1000. PMID: 2643467. 3. Yagisawa N, Shimada N, Naganawa H, Takita T, Hamada M, Takeuchi T, Umezawa H, Nakamura H, Iitaka Y. Oxanosine, a novel nucleoside from actinomycetes. Nucleic Acids Symp Ser. 1981;(10):55-8. PMID: 7031611.
In vitro protocol: 1. Yu R, Kim Y, Maltseva N, Braunstein P, Joachimiak A, Hedstrom L. Oxanosine Monophosphate Is a Covalent Inhibitor of Inosine 5'-Monophosphate Dehydrogenase. Chem Res Toxicol. 2019 Mar 18;32(3):456-466. doi: 10.1021/acs.chemrestox.8b00342. Epub 2019 Feb 25. PMID: 30746940; PMCID: PMC6467267. 2. Itoh O, Kuroiwa S, Atsumi S, Umezawa K, Takeuchi T, Hori M. Induction by the guanosine analogue oxanosine of reversion toward the normal phenotype of K-ras-transformed rat kidney cells. Cancer Res. 1989 Feb 15;49(4):996-1000. PMID: 2643467.
In vivo protocol: 1. Yagisawa N, Shimada N, Naganawa H, Takita T, Hamada M, Takeuchi T, Umezawa H, Nakamura H, Iitaka Y. Oxanosine, a novel nucleoside from actinomycetes. Nucleic Acids Symp Ser. 1981;(10):55-8. PMID: 7031611.

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1: Yu R, Kim Y, Maltseva N, Braunstein P, Joachimiak A, Hedstrom L. Oxanosine Monophosphate Is a Covalent Inhibitor of Inosine 5'-Monophosphate Dehydrogenase. Chem Res Toxicol. 2019 Mar 18;32(3):456-466. doi: 10.1021/acs.chemrestox.8b00342. Epub 2019 Feb 25. PMID: 30746940; PMCID: PMC6467267.

2: Banfi L, Basso A, Chiappe C, De Moliner F, Riva R, Sonaglia L. Development of a stereoselective Ugi reaction starting from an oxanorbornene β-amino acid derivative. Org Biomol Chem. 2012 May 21;10(19):3819-29. doi: 10.1039/c2ob25060h. Epub 2012 Mar 30. PMID: 22461002.

3: Chen HJ, Chiu WL, Lin WP, Yang SS. Investigation of DNA-protein cross-link formation between lysozyme and oxanine by mass spectrometry. Chembiochem. 2008 May 5;9(7):1074-81. doi: 10.1002/cbic.200700686. PMID: 18351683.

4: Majumdar P, Wu H, Tipton P, Glaser R. Oxanosine is a substrate of adenosine deaminase. Implications for the quest for a toxicological marker for nitrosation activity. Chem Res Toxicol. 2005 Dec;18(12):1830-41. doi: 10.1021/tx050232h. PMID: 16359173.

5: Glaser R, Wu H, Lewis M. Cytosine catalysis of nitrosative guanine deamination and interstrand cross-link formation. J Am Chem Soc. 2005 May 25;127(20):7346-58. doi: 10.1021/ja0501159. PMID: 15898783.

6: Nakamura M, Ogawa T, Yokono A, Nakamori S, Ohno T, Umezawa K. Synergistic anti-viral effect of oxanosine and ddI against human immunodeficiency virus. Biomed Pharmacother. 2005 Jan-Feb;59(1-2):47-50. doi: 10.1016/j.biopha.2004.05.017. Epub 2005 Jan 26. PMID: 15740935.

7: Qian M, Glaser R. Demonstration of an alternative mechanism for G-to-G cross- link formation. J Am Chem Soc. 2005 Jan 26;127(3):880-7. doi: 10.1021/ja045108j. PMID: 15656626.

8: Rayat S, Wu Z, Glaser R. Nitrosative guanine deamination: ab initio study of deglycation of N-protonated 5-cyanoimino-4-oxomethylene-4,5-dihydroimidazoles. Chem Res Toxicol. 2004 Sep;17(9):1157-69. doi: 10.1021/tx0499416. PMID: 15377149.

9: Rayat S, Majumdar P, Tipton P, Glaser R. 5-Cyanoimino-4-oxomethylene-4,5-dihydroimidazole and 5-cyanoamino-4-imidazolecarboxylic acid intermediates in nitrosative guanosine deamination: evidence from 18O-labeling experiments. J Am Chem Soc. 2004 Aug 18;126(32):9960-9. doi: 10.1021/ja049835q. PMID: 15303870.

10: Hitchcock TM, Gao H, Cao W. Cleavage of deoxyoxanosine-containing oligodeoxyribonucleotides by bacterial endonuclease V. Nucleic Acids Res. 2004 Aug 2;32(13):4071-80. doi: 10.1093/nar/gkh747. PMID: 15289580; PMCID: PMC506822.

11: Suzuki T, Ide H, Yamada M, Morii T, Makino K. Formation of 2-chloroinosine from guanosine by treatment of HNO(2) in the presence of NaCl. Bioorg Med Chem. 2001 Nov;9(11):2937-41. doi: 10.1016/s0968-0896(01)00173-0. PMID: 11597475.

12: Suzuki T, Yamada M, Ide H, Kanaori K, Tajima K, Morii T, Makino K. Influence of ring opening-closure equilibrium of oxanine, a novel damaged nucleobase, on migration behavior in capillary electrophoresis. J Chromatogr A. 2000 Apr 28;877(1-2):225-32. doi: 10.1016/s0021-9673(00)00178-3. PMID: 10845801.

13: Saito Y, Nakamura M, Ohno T, Chaicharoenpong C, Ichikawa E, Yamamura S, Kato K, Umezawa K. Syntheses of oxanosine and carbocyclic oxanosine derivatives as anti-HIV agents. J Antibiot (Tokyo). 2000 Mar;53(3):309-13. doi: 10.7164/antibiotics.53.309. PMID: 10819305.

14: Saito Y, Chaicharoenpong C, Ohno O, Ichikawa E, Yamamura S, Kato K, Nakamura M, Ohno T, Umezawa K. Synthesis and anti-HIV activity of unusual nucleoside oxanosine derivatives. Nucleic Acids Symp Ser. 1999;(42):19-20. doi: 10.1093/nass/42.1.19. PMID: 10780358.

15: Hernández B, Soliva R, Luque FJ, Orozco M. Misincorporation of 2'-deoxyoxanosine into DNA: a molecular basis for NO-induced mutagenesis derived from theoretical calculations. Nucleic Acids Res. 2000 Dec 15;28(24):4873-83. doi: 10.1093/nar/28.24.4873. PMID: 11121478; PMCID: PMC115229.

16: Suzuki T, Ide H, Yamada M, Endo N, Kanaori K, Tajima K, Morii T, Makino K. Formation of 2'-deoxyoxanosine from 2'-deoxyguanosine and nitrous acid: mechanism and intermediates. Nucleic Acids Res. 2000 Jan 15;28(2):544-51. doi: 10.1093/nar/28.2.544. PMID: 10606654; PMCID: PMC102522.

17: Hiwasa T, Kondo K, Hishiki T, Koshizawa S, Umezawa K, Nakagawara A. GDNF- induced neurite formation was stimulated by protein kinase inhibitors and suppressed by Ras inhibitors. Neurosci Lett. 1997 Dec 5;238(3):115-8. doi: 10.1016/s0304-3940(97)00861-6. PMID: 9464633.

18: Suzuki T, Kanaori K, Tajima K, Makino K. Mechanism and intermediate for formation of 2'-deoxyoxanosine. Nucleic Acids Symp Ser. 1997;(37):313-4. PMID: 9586125.

19: Ota A, Yoshida S, Nomura T, Matsui S, Hagino Y, Umezawa K, Katoh S, Nagatsu T. Tetrahydrobiopterin biosynthesis enhanced by lipopolysaccharide stimulation in murine neuroblastoma cell line N1E-115. J Neurochem. 1996 Dec;67(6):2540-8. doi: 10.1046/j.1471-4159.1996.67062540.x. PMID: 8931488.

20: Osda H. [Differentiation inducing compounds]. Tanpakushitsu Kakusan Koso. 1993 Aug;38(11):1791-9. Japanese. PMID: 8210426.