6-Thioguanosine hydrate
featured

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

MedKoo CAT#: 592197

CAS#: 345909-25-3 (hydrate)

Description: 6-Thioguanosine is an Antineoplastic agent.


Chemical Structure

img
6-Thioguanosine hydrate
CAS# 345909-25-3 (hydrate)

Theoretical Analysis

MedKoo Cat#: 592197
Name: 6-Thioguanosine hydrate
CAS#: 345909-25-3 (hydrate)
Chemical Formula: C10H15N5O6S
Exact Mass: 0.00
Molecular Weight: 333.319
Elemental Analysis: C, 36.03; H, 4.54; N, 21.01; O, 28.80; S, 9.62

Price and Availability

Size Price Availability Quantity
500mg USD 350 2 Weeks
1g USD 520
2g USD 850 2 Weeks
5g USD 1850 2 Weeks
Bulk inquiry

Related CAS #: 85-31-4 (free base)   345909-25-3 (hydrate)    

Synonym: 6-Thioguanosine; NSC-29422; NSC 29422; NSC29422; 6-Thioguanosine hydrate

IUPAC/Chemical Name: 2-Amino-6-mercaptopurin-9-ylriboside hydrate

InChi Key: KDZMJEHYXAFUGI-NZDFUMTISA-N

InChi Code: InChI=1S/C10H13N5O5S.H2O/c11-10-13-7-4(8(21)14-10)12-2-15(7)20-9-6(18)5(17)3(1-16)19-9;/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,21);1H2/t3-,5-,6-,9?;/m1./s1

SMILES Code: O[C@H]([C@@H]([C@@H](CO)O1)O)C1ON2C=NC3=C(S)N=C(N)N=C23.[H]O[H]

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: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 333.32 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:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Inde T, Nishizawa S, Hattori Y, Kanamori T, Yuasa H, Seio K, Sekine M, Ohkubo A. Synthesis of and triplex formation in oligonucleotides containing 2'-deoxy-6-thioxanthosine. Bioorg Med Chem. 2018 Jun 5. pii: S0968-0896(18)30902-7. doi: 10.1016/j.bmc.2018.06.004. [Epub ahead of print] PubMed PMID: 29914771.

2: Supandi S, Harahap Y, Harmita H, Andalusia R. Quantification of 6-Mercaptopurine and Its Metabolites in Patients with Acute Lympoblastic Leukemia Using Dried Blood Spots and UPLC-MS/MS. Sci Pharm. 2018 Apr 25;86(2). pii: E18. doi: 10.3390/scipharm86020018. PubMed PMID: 29693618; PubMed Central PMCID: PMC6027686.

3: Miyata S, Yamada T, Isozaki T, Sugimura H, Xu YZ, Suzuki T. Absorption Characteristics and Quantum Yields of Singlet Oxygen Generation of Thioguanosine Derivatives. Photochem Photobiol. 2018 Jul;94(4):677-684. doi: 10.1111/php.12900. Epub 2018 Mar 31. PubMed PMID: 29420844.

4: Ashwood B, Ortiz-Rodríguez LA, Crespo-Hernández CE. Photochemical relaxation pathways of S(6)-methylthioinosine and O(6)-methylguanosine in solution. Faraday Discuss. 2018 Apr 17;207(0):351-374. doi: 10.1039/c7fd00193b. PubMed PMID: 29372193.

5: Liu X, Chen Y, Fierke CA. Inner-Sphere Coordination of Divalent Metal Ion with Nucleobase in Catalytic RNA. J Am Chem Soc. 2017 Dec 6;139(48):17457-17463. doi: 10.1021/jacs.7b08755. Epub 2017 Nov 22. PubMed PMID: 29116782; PubMed Central PMCID: PMC6020041.

6: Al-Mahamad LLG, El-Zubir O, Smith DG, Horrocks BR, Houlton A. A coordination polymer for the site-specific integration of semiconducting sequences into DNA-based materials. Nat Commun. 2017 Sep 28;8(1):720. doi: 10.1038/s41467-017-00852-6. PubMed PMID: 28959026; PubMed Central PMCID: PMC5620084.

7: Ashwood B, Jockusch S, Crespo-Hernández CE. Excited-State Dynamics of the Thiopurine Prodrug 6-Thioguanine: Can N9-Glycosylation Affect Its Phototoxic Activity? Molecules. 2017 Feb 28;22(3). pii: E379. doi: 10.3390/molecules22030379. PubMed PMID: 28264514.

8: Nishioka T, Oshiro I, Onizuka K, Taniguchi Y, Sasaki S. Efficient Thymidine-Selective DNA Interstrand Photo-activated Crosslinking by the 6-Thioguanine Connected via an Ethylene-Linker to the 2'-Deoxyribose Unit. Chem Pharm Bull (Tokyo). 2016;64(9):1315-20. doi: 10.1248/cpb.c16-00310. PubMed PMID: 27581636.

9: Kowalska J, Martin F, Jemielity J. Synthetic Capped mRNAs for Cap-Specific Photo-Cross-Linking Experiments. Methods Mol Biol. 2016;1428:31-43. doi: 10.1007/978-1-4939-3625-0_2. PubMed PMID: 27236790.

10: Shin JY, Wey M, Umutesi HG, Sun X, Simecka J, Heo J. Thiopurine Prodrugs Mediate Immunosuppressive Effects by Interfering with Rac1 Protein Function. J Biol Chem. 2016 Jun 24;291(26):13699-714. doi: 10.1074/jbc.M115.694422. Epub 2016 May 9. PubMed PMID: 27189938; PubMed Central PMCID: PMC4919453.

11: Berthelier V, Harris JB, Estenson KN, Baudry J. Discovery of an inhibitor of Z-alpha1 antitrypsin polymerization. PLoS One. 2015 May 11;10(5):e0126256. doi: 10.1371/journal.pone.0126256. eCollection 2015. PubMed PMID: 25961288; PubMed Central PMCID: PMC4427445.

12: Oshiro I, Jitsuzaki D, Onizuka K, Nishimoto A, Taniguchi Y, Sasaki S. Site-specific modification of the 6-amino group of adenosine in RNA by an interstrand functionality-transfer reaction with an s-functionalized 4-thiothymidine. Chembiochem. 2015 May 26;16(8):1199-204. doi: 10.1002/cbic.201500084. Epub 2015 May 4. PubMed PMID: 25940822.

13: De Nicolò A, Agnesod D, Simiele M, Riganò D, Adriani A, Canaparo R, Astegiano M, Rizzetto M, Di Perri G, D'Avolio A. UPLC-MS/MS method for quantification of the azathioprine metabolites 6-mercaptoguanosine and 6-methylmercaptopurine riboside in peripheral blood mononuclear cells. J Pharm Biomed Anal. 2014 Sep;98:271-8. doi: 10.1016/j.jpba.2014.05.040. Epub 2014 Jun 7. PubMed PMID: 24960235.

14: Jitsuzaki D, Onizuka K, Nishimoto A, Oshiro I, Taniguchi Y, Sasaki S. Remarkable acceleration of a DNA/RNA inter-strand functionality transfer reaction to modify a cytosine residue: the proximity effect via complexation with a metal cation. Nucleic Acids Res. 2014 Jul;42(13):8808-15. doi: 10.1093/nar/gku538. Epub 2014 Jun 23. PubMed PMID: 24957600; PubMed Central PMCID: PMC4117767.

15: Nowakowska M, Kowalska J, Martin F, d'Orchymont A, Zuberek J, Lukaszewicz M, Darzynkiewicz E, Jemielity J. Cap analogs containing 6-thioguanosine--reagents for the synthesis of mRNAs selectively photo-crosslinkable with cap-binding biomolecules. Org Biomol Chem. 2014 Jul 21;12(27):4841-7. doi: 10.1039/c4ob00059e. PubMed PMID: 24763507.

16: Xiao Y, Ji D, Guo L, Wang Y. Comprehensive characterization of (S)GTP-binding proteins by orthogonal quantitative (S)GTP-affinity profiling and (S)GTP/GTP competition assays. Anal Chem. 2014 May 6;86(9):4550-8. doi: 10.1021/ac500588q. Epub 2014 Apr 11. PubMed PMID: 24689502; PubMed Central PMCID: PMC4014148.

17: Marinković G, Kroon J, Hoogenboezem M, Hoeben KA, Ruiter MS, Kurakula K, Otermin Rubio I, Vos M, de Vries CJ, van Buul JD, de Waard V. Inhibition of GTPase Rac1 in endothelium by 6-mercaptopurine results in immunosuppression in nonimmune cells: new target for an old drug. J Immunol. 2014 May 1;192(9):4370-8. doi: 10.4049/jimmunol.1302527. Epub 2014 Mar 26. PubMed PMID: 24670805.

18: Pesek JJ, Matyska MT, Young JE. Analysis of thiopurines using aqueous normal phase chromatography. J Pharm Biomed Anal. 2014 Jul;95:102-6. doi: 10.1016/j.jpba.2014.02.019. Epub 2014 Mar 3. PubMed PMID: 24657678.

19: Amo-Ochoa P, Alexandre SS, Hribesh S, Galindo MA, Castillo O, Gómez-García CJ, Pike AR, Soler JM, Houlton A, Zamora F, Harrington RW, Clegg W. Coordination chemistry of 6-thioguanine derivatives with cobalt: toward formation of electrical conductive one-dimensional coordination polymers. Inorg Chem. 2013 May 6;52(9):5290-9. doi: 10.1021/ic400237h. Epub 2013 Apr 18. Erratum in: Inorg Chem.2013 Jun 17;52(12):7306. Harrington, Ross W [added]; Clegg, William [added]. PubMed PMID: 23594219.

20: Singh NK, Pakkkianathan BC, Kumar M, Daddam JR, Jayavel S, Kannan M, Pillai GG, Krishnan M. Computational studies on molecular interactions of 6-thioguanosine analogs with anthrax toxin receptor 1. Interdiscip Sci. 2012 Sep;4(3):183-9. doi: 10.1007/s12539-012-0126-9. Epub 2013 Jan 8. PubMed PMID: 23292691.