6-Benzylthioinosine

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

MedKoo CAT#: 561824

CAS#: 6165-03-0

Description: 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

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6-Benzylthioinosine
CAS# 6165-03-0

Theoretical Analysis

MedKoo Cat#: 561824
Name: 6-Benzylthioinosine
CAS#: 6165-03-0
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 not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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

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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1: Sabnis HS, Bradley HL, Tripathi S, Yu WM, Tse W, Qu CK, Bunting KD. Synergistic cell death in FLT3-ITD positive acute myeloid leukemia by combined treatment with metformin and 6-benzylthioinosine. Leuk Res. 2016 Nov;50:132-140. doi: 10.1016/j.leukres.2016.10.004. Epub 2016 Oct 5. PubMed PMID: 27760406; PubMed Central PMCID: PMC5083204.

2: Zang S, Liu N, Wang H, Wald DN, Shao N, Zhang J, Ma D, Ji C, Tse W. Wnt signaling is involved in 6-benzylthioinosine-induced AML cell differentiation. BMC Cancer. 2014 Nov 27;14:886. doi: 10.1186/1471-2407-14-886. PubMed PMID: 25428027; PubMed Central PMCID: PMC4289047.

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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.

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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. Antimicrob Agents Chemother. 1999 Oct;43(10):2437-43. PubMed PMID: 10508021; PubMed Central PMCID: PMC89497.

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