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MedKoo Cat#: 561824 | Name: 6-Benzylthioinosine

Description:

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

6-Benzylthioinosine is a broad-spectrum metabolic inhibitor. It acts by inhibiting glucose uptake, decreasing glycolysis and ATP concentration with minimal changes in ROS and mitochondrial respiration.

Chemical Structure

6-Benzylthioinosine
6-Benzylthioinosine
CAS#6165-03-3

Theoretical Analysis

MedKoo Cat#: 561824

Name: 6-Benzylthioinosine

CAS#: 6165-03-3

Chemical Formula: C17H18N4O4S

Exact Mass: 374.1049

Molecular Weight: 374.41

Elemental Analysis: C, 54.53; H, 4.85; N, 14.96; O, 17.09; S, 8.56

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
6165-03-3
Synonym
6-Benzylthioinosine; 6Benzylthioinosine; 6-BT; 6-Bn-thioinosine;
IUPAC/Chemical Name
(2R,3R,4S,5R)-2-(6-Benzylsulfanylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
InChi Key
OMJRXFOHHLLDFR-LSCFUAHRSA-N
InChi Code
InChI=1S/C17H18N4O4S/c22-6-11-13(23)14(24)17(25-11)21-9-20-12-15(21)18-8-19-16(12)26-7-10-4-2-1-3-5-10/h1-5,8-9,11,13-14,17,22-24H,6-7H2/t11-,13-,14-,17-/m1/s1
SMILES Code
O[C@H]1[C@H](N2C=NC3=C(SCC4=CC=CC=C4)N=CN=C23)O[C@H](CO)[C@H]1O
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
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 374.41 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
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PubMed PMID: 22621920; PubMed Central PMCID: PMC3390638. 4: Al Safarjalani ON, Rais RH, Kim YA, Chu CK, Naguib FN, El Kouni MH. Carbocyclic 6-benzylthioinosine analogues as subversive substrates of Toxoplasma gondii adenosine kinase: biological activities and selective toxicities. Biochem Pharmacol. 2010 Oct 1;80(7):955-63. doi: 10.1016/j.bcp.2010.06.001. Epub 2010 Jun 10. PubMed PMID: 20541538; PubMed Central PMCID: PMC2923275. 5: Kim YA, Rawal RK, Yoo J, Sharon A, Jha AK, Chu CK, Rais RH, Al Safarjalani ON, Naguib FN, El Kouni MH. Structure-activity relationships of carbocyclic 6-benzylthioinosine analogues as subversive substrates of Toxoplasma gondii adenosine kinase. Bioorg Med Chem. 2010 May 15;18(10):3403-12. doi: 10.1016/j.bmc.2010.04.003. Epub 2010 Apr 8. PubMed PMID: 20456959. 6: Li L, Xu Y, Wald DN, Tse W. Determination of 6-benzylthioinosine in mouse and human plasma by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Nov 15;877(30):3871-7. doi: 10.1016/j.jchromb.2009.09.035. Epub 2009 Oct 1. PubMed PMID: 19836317. 7: Al Safarjalani ON, Rais RH, Kim YA, Chu CK, Naguib FN, el Kouni MH. 7-Deaza-6-benzylthioinosine analogues as subversive substrate of Toxoplasma gondii adenosine kinase: activities and selective toxicities. Biochem Pharmacol. 2008 Oct 15;76(8):958-66. doi: 10.1016/j.bcp.2008.07.035. Epub 2008 Aug 7. PubMed PMID: 18755159; PubMed Central PMCID: PMC2581922. 8: Kim YA, Sharon A, Chu CK, Rais RH, Al Safarjalani ON, Naguib FN, el Kouni MH. Structure-activity relationships of 7-deaza-6-benzylthioinosine analogues as ligands of Toxoplasma gondii adenosine kinase. J Med Chem. 2008 Jul 10;51(13):3934-45. doi: 10.1021/jm800201s. Epub 2008 Jun 19. PubMed PMID: 18563892. 9: Wald DN, Vermaat HM, Zang S, Lavik A, Kang Z, Peleg G, Gerson SL, Bunting KD, Agarwal ML, Roth BL, Tse W. Identification of 6-benzylthioinosine as a myeloid leukemia differentiation-inducing compound. Cancer Res. 2008 Jun 1;68(11):4369-76. doi: 10.1158/0008-5472.CAN-07-6559. PubMed PMID: 18519698; PubMed Central PMCID: PMC3896053. 10: Kim YA, Sharon A, Chu CK, Rais RH, Al Safarjalani ON, Naguib FN, el Kouni MH. Synthesis, biological evaluation and molecular modeling studies of N6-benzyladenosine analogues as potential anti-toxoplasma agents. Biochem Pharmacol. 2007 May 15;73(10):1558-72. Epub 2007 Jan 21. PubMed PMID: 17306769; PubMed Central PMCID: PMC2064036. 11: Galazka J, Striepen B, Ullman B. Adenosine kinase from Cryptosporidium parvum. Mol Biochem Parasitol. 2006 Oct;149(2):223-30. Epub 2006 Jun 27. PubMed PMID: 16879885. 12: Gupte A, Buolamwini JK, Yadav V, Chu CK, Naguib FN, el Kouni MH. 6-Benzylthioinosine analogues: promising anti-toxoplasmic agents as inhibitors of the mammalian nucleoside transporter ENT1 (es). Biochem Pharmacol. 2005 Dec 19;71(1-2):69-73. Epub 2005 Nov 23. PubMed PMID: 16310172. 13: Rais RH, Al Safarjalani ON, Yadav V, Guarcello V, Kirk M, Chu CK, Naguib FN, el Kouni MH. 6-Benzylthioinosine analogues as subversive substrate of Toxoplasma gondii adenosine kinase: activities and selective toxicities. Biochem Pharmacol. 2005 May 15;69(10):1409-19. PubMed PMID: 15857605. 14: Tromp RA, Spanjersberg RF, von Frijtag Drabbe Künzel JK, IJzerman AP. Inhibition of nucleoside transport proteins by C8-alkylamine-substituted purines. J Med Chem. 2005 Jan 13;48(1):321-9. PubMed PMID: 15634027. 15: Yadav V, Chu CK, Rais RH, Al Safarjalani ON, Guarcello V, Naguib FN, el Kouni MH. Synthesis, biological activity and molecular modeling of 6-benzylthioinosine analogues as subversive substrates of Toxoplasma gondii adenosine kinase. J Med Chem. 2004 Apr 8;47(8):1987-96. PubMed PMID: 15055998. 16: el Kouni MH, Guarcello V, Al Safarjalani ON, Naguib FN. Metabolism and selective toxicity of 6-nitrobenzylthioinosine in Toxoplasma gondii. 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