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MedKoo Cat#: 592280 | Name: Xanthosine
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Description:

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

Xanthosine, a purine nucleoside composed of xanthine and ribose, has demonstrated various bioactivities, particularly in cellular metabolism and proliferation. It has been shown to influence stem cell biology, notably promoting the proliferation of bovine mammary epithelial stem-like cells and increasing milk yield in dairy cows through enhanced alveolar development. In murine models, xanthosine administration has been linked to altered hematopoietic stem cell dynamics. In vitro, xanthosine can inhibit inosine monophosphate dehydrogenase (IMPDH), affecting guanine nucleotide synthesis, which may modulate lymphocyte proliferation.

Chemical Structure

Xanthosine
Xanthosine
CAS#146-80-5 (free)

Theoretical Analysis

MedKoo Cat#: 592280

Name: Xanthosine

CAS#: 146-80-5 (free)

Chemical Formula: C10H12N4O6

Exact Mass: 284.0757

Molecular Weight: 284.23

Elemental Analysis: C, 42.26; H, 4.26; N, 19.71; O, 33.77

Price and Availability

Size Price Availability Quantity
500mg USD 350.00 2 Weeks
1g USD 550.00 2 Weeks
2g USD 950.00 2 Weeks
5g USD 1,650.00 2 Weeks
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Related CAS #
5968-90-1 (hydrate) 146-80-5 (free)
Synonym
Xanthosine; NSC 18930; NSC-18930; NSC18930
IUPAC/Chemical Name
9-beta-D-Ribofuranosylxanthine
InChi Key
UBORTCNDUKBEOP-UUOKFMHZSA-N
InChi Code
InChI=1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)/t3-,5-,6-,9-/m1/s1
SMILES Code
OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3=C(N=C(N=C32)O)O)O1)O)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
>3 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
2934.99.03.00
More Info

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
1: Westarp S, Brandt F, Neumair L, Betz C, Dagane A, Kemper S, Jacob CR, Neubauer P, Kurreck A, Kaspar F. Nucleoside Phosphorylases make N7-xanthosine. Nat Commun. 2024 Apr 29;15(1):3625. doi: 10.1038/s41467-024-47287-4. PMID: 38684649; PMCID: PMC11058261. 2: Doshi M, Natori Y, Ishii A, Saigusa D, Watanabe S, Hosoyamada M, Hirashima- Akae Y. Hypothermia increases adenosine monophosphate and xanthosine monophosphate levels in the mouse hippocampus, preventing their reduction by global cerebral ischemia. Sci Rep. 2024 Feb 7;14(1):3187. doi: 10.1038/s41598-024-53530-1. PMID: 38326353; PMCID: PMC10850059. 3: Ahmed SA, Sarma P, Barge SR, Swargiary D, Devi GS, Borah JC. Xanthosine, a purine glycoside mediates hepatic glucose homeostasis through inhibition of gluconeogenesis and activation of glycogenesis via regulating the AMPK/ FoxO1/AKT/GSK3β signaling cascade. Chem Biol Interact. 2023 Feb 1;371:110347. doi: 10.1016/j.cbi.2023.110347. Epub 2023 Jan 7. PMID: 36627075. 4: Mair S, Erharter K, Renard E, Brillet K, Brunner M, Lusser A, Kreutz C, Ennifar E, Micura R. Towards a comprehensive understanding of RNA deamination: synthesis and properties of xanthosine-modified RNA. Nucleic Acids Res. 2022 Jun 24;50(11):6038-6051. doi: 10.1093/nar/gkac477. PMID: 35687141; PMCID: PMC9226506. 5: Heinemann KJ, Yang SY, Straube H, Medina-Escobar N, Varbanova-Herde M, Herde M, Rhee S, Witte CP. Initiation of cytosolic plant purine nucleotide catabolism involves a monospecific xanthosine monophosphate phosphatase. Nat Commun. 2021 Nov 25;12(1):6846. doi: 10.1038/s41467-021-27152-4. PMID: 34824243; PMCID: PMC8616923. 6: Oka N, Hirabayashi H, Kumada K, Ando K. Synthesis of xanthosine 2-phosphate diesters via phosphitylation of the carbonyl group. Bioorg Med Chem Lett. 2021 Dec 15;54:128439. doi: 10.1016/j.bmcl.2021.128439. Epub 2021 Nov 5. PMID: 34748937. 7: Baccolini C, Witte CP. AMP and GMP Catabolism in Arabidopsis Converge on Xanthosine, Which Is Degraded by a Nucleoside Hydrolase Heterocomplex. Plant Cell. 2019 Mar;31(3):734-751. doi: 10.1105/tpc.18.00899. Epub 2019 Feb 20. PMID: 30787180; PMCID: PMC6482636. 8: Choudhary RK, Choudhary S, Pathak D, Udehiya R, Verma R, Kaswan S, Sharma A, Gupta D, Honparkhe M, Capuco AV. Evaluation of xanthosine treatment on gene expression of mammary glands in early lactating goats. J Dairy Res. 2018 Aug;85(3):288-294. doi: 10.1017/S0022029918000493. PMID: 30156522. 9: Choudhary S, Li W, Bickhart D, Verma R, Sethi RS, Mukhopadhyay CS, Choudhary RK. Examination of the xanthosine response on gene expression of mammary epithelial cells using RNA-seq technology. J Anim Sci Technol. 2018 Jul 13;60:18. doi: 10.1186/s40781-018-0177-5. PMID: 30009039; PMCID: PMC6045846. 10: Choudhary RK, Choudhary S, Verma R. In vivo response of xanthosine on mammary gene expression of lactating Beetal goat. Mol Biol Rep. 2018 Aug;45(4):581-590. doi: 10.1007/s11033-018-4196-6. Epub 2018 May 26. PMID: 29804277. 11: Röttger K, Stellmacher R, Stuhldreier MC, Temps F. Ultrafast Electronic Deactivation Dynamics of Xanthosine Monophosphate. Molecules. 2017 Jan 18;22(1):160. doi: 10.3390/molecules22010160. PMID: 28106804; PMCID: PMC6155666. 12: Qian P, Guo HB, Yue Y, Wang L, Yang X, Guo H. Correction to Understanding the Catalytic Mechanism of Xanthosine Methyltransferase in Caffeine Biosynthesis from QM/MM Molecular Dynamics and Free Energy Simulations. J Chem Inf Model. 2016 Nov 28;56(11):2280. doi: 10.1021/acs.jcim.6b00634. Epub 2016 Oct 28. Erratum for: J Chem Inf Model. 2016 Sep 26;56(9):1755-61. doi: 10.1021/acs.jcim.6b00153. PMID: 27790913. 13: Qian P, Guo HB, Yue Y, Wang L, Yang X, Guo H. Understanding the Catalytic Mechanism of Xanthosine Methyltransferase in Caffeine Biosynthesis from QM/MM Molecular Dynamics and Free Energy Simulations. J Chem Inf Model. 2016 Sep 26;56(9):1755-61. doi: 10.1021/acs.jcim.6b00153. Epub 2016 Aug 15. Erratum in: J Chem Inf Model. 2016 Nov 28;56(11):2280. doi: 10.1021/acs.jcim.6b00634. PMID: 27482605. 14: Rauner G, Barash I. Xanthosine administration does not affect the proportion of epithelial stem cells in bovine mammary tissue, but has a latent negative effect on cell proliferation. Exp Cell Res. 2014 Oct 15;328(1):186-196. doi: 10.1016/j.yexcr.2014.06.017. Epub 2014 Jun 30. PMID: 24992045. 15: Dong WR, Sun CC, Zhu G, Hu SH, Xiang LX, Shao JZ. New function for Escherichia coli xanthosine phophorylase (xapA): genetic and biochemical evidences on its participation in NAD(+) salvage from nicotinamide. BMC Microbiol. 2014 Feb 8;14:29. doi: 10.1186/1471-2180-14-29. PMID: 24506841; PMCID: PMC3923242. 16: Dahncke K, Witte CP. Plant purine nucleoside catabolism employs a guanosine deaminase required for the generation of xanthosine in Arabidopsis. Plant Cell. 2013 Oct;25(10):4101-9. doi: 10.1105/tpc.113.117184. Epub 2013 Oct 15. PMID: 24130159; PMCID: PMC3877791. 17: Bourke CA. Motor neurone disease in molybdenum-deficient sheep fed the endogenous purine xanthosine: possible mechanism for Tribulus staggers. Aust Vet J. 2012 Jul;90(7):272-4. doi: 10.1111/j.1751-0813.2012.00947.x. PMID: 22731949. 18: Choudhary RK, Capuco AV. In vitro expansion of the mammary stem/progenitor cell population by xanthosine treatment. BMC Cell Biol. 2012 Jun 14;13:14. doi: 10.1186/1471-2121-13-14. PMID: 22698263; PMCID: PMC3407777. 19: Gogia S, Balaram H, Puranik M. Hypoxanthine guanine phosphoribosyltransferase distorts the purine ring of nucleotide substrates and perturbs the pKa of bound xanthosine monophosphate. Biochemistry. 2011 May 17;50(19):4184-93. doi: 10.1021/bi102039b. Epub 2011 Apr 25. PMID: 21486037. 20: Zhang Z, Wauchope OR, Seley-Radtke KL. Mechanistic studies in the synthesis of a series of thieno-expanded xanthosine and guanosine nucleosides. Tetrahedron. 2008 Nov 24;64(48):10791-10797. doi: 10.1016/j.tet.2008.09.011. PMID: 19946353; PMCID: PMC2629406

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