Xanthopterin

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

MedKoo CAT#: 558599

CAS#: 119-44-8

Description: Xanthopterin is a yellow, crystalline solid that inhibits the growth of lymphocytes produced by concanavalin.


Price and Availability

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Xanthopterin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 558599
Name: Xanthopterin
CAS#: 119-44-8
Chemical Formula: C6H5N5O2
Exact Mass: 179.04
Molecular Weight: 179.14
Elemental Analysis: C, 40.23; H, 2.81; N, 39.10; O, 17.86


Synonym: Xanthopterin; Ksantopterin;

IUPAC/Chemical Name: 2-Aminopteridine-4(3H),6(5H)-dione

InChi Key: VURKRJGMSKJIQX-UHFFFAOYSA-N

InChi Code: InChI=1S/C6H5N5O2/c7-6-10-4-3(5(13)11-6)9-2(12)1-8-4/h1H,(H,9,12)(H3,7,8,10,11,13)

SMILES Code: O=C1NC2=C(N=C(N)NC2=O)N=C1


Technical Data

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).

Harmonized System Code:
2934.99.03.00


References

1: Wan YQ, Tang LJ, Tan T. Simultaneous determination of xanthopterin and isoxanthopterin in human urine by synchronous fluorescence spectroscopy. J Fluoresc. 2010 Nov;20(6):1191-8. doi: 10.1007/s10895-010-0667-4. Epub 2010 Apr 24. PubMed PMID: 20419340.

2: Lord JL, de Peyster A, Quintana PJ, Metzger RP. Cytotoxicity of xanthopterin and isoxanthopterin in MCF-7 cells. Cancer Lett. 2005 May 10;222(1):119-24. PubMed PMID: 15837549.

3: Bakir AA, Shaykh M, Williams RH, Ahmed S, Dunea G. A study of xanthopterin in chronic renal failure. Am J Nephrol. 1992;12(4):224-8. PubMed PMID: 1481869.

4: Fukuda A, Mazda T, Gyure WL, Iino T, Harada H, Yakura M, Kamitsukasa H, Ohbayashi A, Oka T, Tsusué M. A comparative study of urinary xanthopterin and neopterin in liver diseases. Eur J Clin Chem Clin Biochem. 1993 Mar;31(3):129-34. PubMed PMID: 8490058.

5: Gogichaishvili S, Johnson J, Gvarjaladze D, Lomidze L, Kankia B. Isothermal amplification of DNA using quadruplex primers with fluorescent pteridine base analogue 3-methyl isoxanthopterin. Biopolymers. 2014 Jun;101(6):583-90. doi: 10.1002/bip.22421. PubMed PMID: 24122726.

6: Rubenstein M, Muchnik S, Garber SL, Arruda JA, Dunea G. Differential effect of xanthopterin and biopterin on cell growth. Int J Biochem. 1993 Dec;25(12):1873-80. PubMed PMID: 8138025.

7: Ziegler I. Pterins and the regulation of lymphocyte activation on the mode of xanthopterin action. Hoppe Seylers Z Physiol Chem. 1984 Jun;365(6):667-73. PubMed PMID: 6207092.

8: Malinen AM, Turtola M, Belogurov GA. Monitoring translocation of multisubunit RNA polymerase along the DNA with fluorescent base analogues. Methods Mol Biol. 2015;1276:31-51. doi: 10.1007/978-1-4939-2392-2_3. PubMed PMID: 25665557.

9: Plotkin M, Volynchik S, Ermakov NY, Benyamini A, Boiko Y, Bergman DJ, Ishay JS. Xanthopterin in the Oriental hornet (Vespa orientalis): light absorbance is increased with maturation of yellow pigment granules. Photochem Photobiol. 2009 Jul-Aug;85(4):955-61. doi: 10.1111/j.1751-1097.2008.00526.x. Epub 2009 Feb 13. PubMed PMID: 19222794.

10: Johnson NP, Ji H, Steinberg TH, von Hippel PH, Marcus AH. Sequence-Dependent Conformational Heterogeneity and Proton-Transfer Reactivity of the Fluorescent Guanine Analogue 6-Methyl Isoxanthopterin (6-MI) in DNA. J Phys Chem B. 2015 Oct 8;119(40):12798-807. doi: 10.1021/acs.jpcb.5b06361. Epub 2015 Sep 25. PubMed PMID: 26368400; PubMed Central PMCID: PMC4948594.

11: Huang L, Guo L, Wan Y, Pan P, Feng L. Simultaneous determination of three potential cancer biomarkers in rat urine by synchronous fluorescence spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc. 2014;120:595-601. doi: 10.1016/j.saa.2013.12.001. Epub 2013 Dec 4. PubMed PMID: 24365397.

12: Garber SL, Salmassi J, Arruda JA, Dunea G. Xanthopterin-induced renal dysfunction: a reversible model of crystal nephropathy. Nephron. 1995;69(1):71-8. PubMed PMID: 7891801.

13: Williams RH, Shaykh M, Ahmed S, Musiala T, Bazilinski N, Dunea G, Dubin A. Purification and biochemical characterization of xanthopterin from patients with chronic renal failure. II. Biochemical elucidation and structural analysis. Clin Biochem. 1991 Oct;24(5):407-15. PubMed PMID: 1760879.

14: ELION GB, LIGHT AE, HITCHINGS GH. The preparation of xanthopterin. J Am Chem Soc. 1949 Feb;71(2):741. PubMed PMID: 18112077.

15: NORRIS ER, MAJNARICH JJ. Xanthopterin in rat anemia produced by sulfathiazole. Am J Physiol. 1948 Jan 1;152(1):179-82. PubMed PMID: 18903442.

16: Roe FJ, Boyland E, Dukes CE, Mitchley BC. Failure of testosterone or xanthopterin to influence the induction of renal neoplasms by lead in rats. Br J Cancer. 1965 Dec;19(4):860-6. PubMed PMID: 5862663; PubMed Central PMCID: PMC2071403.

17: NORRIS ER, MAJNARICH JJ. Influence of the dosage of xanthopterin upon the response in hemapoiesis. Am J Physiol. 1948 Apr;153(1):133-7. PubMed PMID: 18867045.

18: Jose D, Weitzel SE, Baase WA, Michael MM, von Hippel PH. Mapping the interactions of the single-stranded DNA binding protein of bacteriophage T4 (gp32) with DNA lattices at single nucleotide resolution: polynucleotide binding and cooperativity. Nucleic Acids Res. 2015 Oct 30;43(19):9291-305. doi: 10.1093/nar/gkv818. Epub 2015 Aug 14. PubMed PMID: 26275774; PubMed Central PMCID: PMC4627071.

19: GONNARD P. [Action of xanthopterin on melanin formation in vitro]. Ann Pharm Fr. 1953 Jun;11(6):446-9. Undetermined Language. PubMed PMID: 13092701.

20: LANG K, SIEBERT G, GANSS E. [Effect of xanthopterin on phosphatases]. Klin Wochenschr. 1951 Jun 1;29(21-22):391. Undetermined Language. PubMed PMID: 14851648.