An active metabolite of 6-thioguanine and azathioprine
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6-Thioguanosine-5'-O-triphosphate (sodium salt)

Item No. 38390

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-thio-guanosine 5′-(tetrahydrogen triphosphate), tetrasodium salt
Synonyms
  • 6-Thio-GTP
Molecular Formula
C10H12N5O13P3S • 4Na
Formula Weight
627.2
Purity
≥98%
Formulation (Request formulation change)
A solution in water
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
O[C@@H]1[C@H](O)[C@@H](COP([O-])(OP(OP([O-])([O-])=O)([O-])=O)=O)O[C@H]1N2C=NC3=C2NC(N)=NC3=S.[Na+].[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C10H16N5O13P3S.4Na/c11-10-13-7-4(8(32)14-10)12-2-15(7)9-6(17)5(16)3(26-9)1-25-30(21,22)28-31(23,24)27-29(18,19)20;;;;/h2-3,5-6,9,16-17H,1H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,32);;;;/q;4*+1/p-4/t3-,5-,6-,9-;;;;/m1..../s1
InChi Key
BWHDSNGJMGUHLZ-ZVQJTLEUSA-J
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    2.7 mg

    $355

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    Product Description

    6-Thioguanosine-5’-O-triphosphate (6-thio-GTP) is an active metabolite of the purine analog 6-thioguanine (Item No. 15774) and the immunosuppressive purine analog azathioprine (Item No. 13987).1,2 It is formed from 6-thioguanine via 6-thio-GMP and 6-thio-GDP intermediates by phosphorylation and from azathioprine via 6-mercaptopurine (Item No. 23675), 6-thio-GMP, and 6-thio-GDP intermediates by a non-enzymatic process and several enzymatic reactions. 6-thio-GTP binds to a variety of GTPases, including Rac, Ras, Cdc42, and RhoA but selectively inhibits activation of Rac1 and Rac2 over Cdc42 in primary human CD4+ T cells stimulated with anti-CD3 and anti-CD28 antibodies.3,4 It inhibits T cell receptor-stimulated proliferation of T cells and reduces CD28-dependent T cell survival in vitro in isolated mouse splenocytes.5 6-Thio-GTP (0.5 mg/kg) increases survival in a mouse model of heart transplantation.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hawwa, A.F., Millership, J.S., Collier, P.A., et al. Pharmacogenomic studies of the anticancer and immunosuppressive thiopurines mercaptopurine and azathioprine. Br. J. Clin. Pharmacol. 66(4), 517-528 (2008).

    2. Neurath, M.F., Kiesslich, R., Teichgraber, U., et al. 6-Thioguanosine diphosphate and triphosphate levels in red blood cells and response to azathioprine therapy in Crohn’s disease. Clin. Gastroenterol. Hepatol. 3(10), 1007-1014 (2005).

    3. Tiede, I., Fritz, G., Strand, S., et al. CD28-dependent Rac1 activation is the molecular target of azathioprine in primary human CD4+ T lymphocytes. J. Clin. Invest. 111(8), 1133-1145 (2003).

    4. Poppe, D., Tiede, I., Fritz, G., et al. Azathioprine suppresses ezrin-radixin-moesin-dependent T cell-APC conjugation through inhibition of Vav guanosine exchange activity on Rac proteins. J. Immunol. 176(1), 640-651 (2006).

    5. Wang, S., Diao, H., Guan, Q., et al. Enhanced cardiac allograft survival by Vav1-Rac signaling blockade in a mouse model. Transpl. Immunol. 18(1), 53-61 (2007).