O6-Benzylguanine| CAS#19916-73-5 | MGMT inhibitor

MedKoo Cat#: 540041 | Name: O6-Benzylguanine

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Description:

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

O(6)-Benzylguanine is an MGMT inhibitor that prevents the repair of DNA damage induced by chemotherapeutics. It allows apoptosis and other mechanisms of cell death to occur. O6-Benzylguanine provides a means to effectively inactivate the AGT protein and increase the chemotherapeutic effectiveness of chloroethylating and methylating agents in vitro and in human tumor xenograft models.

Chemical Structure

O6-Benzylguanine

CAS#19916-73-5 (free)

Theoretical Analysis

MedKoo Cat#: 540041

Name: O6-Benzylguanine

CAS#: 19916-73-5 (free)

Chemical Formula: C12H11N5O

Exact Mass: 241.0964

Molecular Weight: 241.25

Elemental Analysis: C, 59.74; H, 4.60; N, 29.03; O, 6.63

Price and Availability

Size	Price	Availability
50mg	USD 350.00	2 Weeks
250mg	USD 750.00	2 Weeks
1g	USD 1,250.00	2 Weeks

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Related CAS #

100994-97-6 (sodium) 19916-73-5 (free)

Synonym

O(6)-Benzylguanine; CCRIS 9383; CCRIS9383; CCRIS-9383; NSC637037; NSC 637037; NSC-637037

IUPAC/Chemical Name

6-(benzyloxy)-1H-purin-2-amine

InChi Key

KRWMERLEINMZFT-UHFFFAOYSA-N

InChi Code

InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17)

SMILES Code

NC1=NC2=NC=NC2=C(OCC3=CC=CC=C3)N1

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 241.25 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.

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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Biomed Pharmacother. 2023 Nov;167:115631. doi: 10.1016/j.biopha.2023.115631. Epub 2023 Oct 5. PMID: 37804814. 4: Gonzalez-Aponte MF, Damato AR, Trebucq LL, Simon T, Cárdenas-García SP, Cho K, Patti GJ, Golombek DA, Chiesa JJ, Herzog ED. Circadian regulation of MGMT expression and promoter methylation underlies daily rhythms in TMZ sensitivity in glioblastoma. bioRxiv [Preprint]. 2023 Sep 17:2023.09.13.557630. doi: 10.1101/2023.09.13.557630. Update in: J Neurooncol. 2024 Feb;166(3):419-430. doi: 10.1007/s11060-023-04535-9. PMID: 37745358; PMCID: PMC10515960. 5: Wang Y, He Y, Ye X, Zhang Y, Huang X, Liu H, Dong W, Yang D, Guo D. Target immobilization on glass microfiber membranes as a label-free strategy for hit identification. Anal Bioanal Chem. 2023 Nov;415(27):6743-6755. doi: 10.1007/s00216-023-04951-w. Epub 2023 Sep 21. PMID: 37730920. 6: Bai P, Fan T, Wang X, Zhao L, Zhong R, Sun G. Modulating MGMT expression through interfering with cell signaling pathways. Biochem Pharmacol. 2023 Sep;215:115726. doi: 10.1016/j.bcp.2023.115726. Epub 2023 Jul 29. PMID: 37524206. 7: Li D, Wang X, Han K, Sun Y, Ren T, Sun G, Zhang N, Zhao L, Zhong R. Hypoxia and CD44 receptors dual-targeted nano-micelles with AGT-inhibitory activity for the targeting delivery of carmustine. Int J Biol Macromol. 2023 Aug 15;246:125657. doi: 10.1016/j.ijbiomac.2023.125657. Epub 2023 Jul 2. PMID: 37399878. 8: He Y, Chen QW, Yu JX, Qin SY, Liu WL, Ma YH, Chen XS, Zhang AQ, Zhang XZ, Cheng YJ. Yeast cell membrane-camouflaged PLGA nanoparticle platform for enhanced cancer therapy. J Control Release. 2023 Jul;359:347-358. doi: 10.1016/j.jconrel.2023.05.043. Epub 2023 Jun 14. PMID: 37277054. 9: Chu W, Houston ZH, Fletcher NL, Huda P, Ahamed M, Lim TX, Day BW, Pinkham M, Thurecht KJ. Development and Validation of a Targeted Treatment for Brain Tumors Using a Multi-Drug Loaded, Relapse-Resistant Polymeric Theranostic. Biomacromolecules. 2023 Jun 12;24(6):2674-2690. doi: 10.1021/acs.biomac.3c00138. Epub 2023 May 4. PMID: 37143361. 10: Barnes JP, Yang SM, Thompson TS, Guevarra CM, Pleasant SS, Do TQ, Crouch RD. Mechanistic Investigation of the Time-Dependent Aldehyde Oxidase Inhibitor Hydralazine. Drug Metab Dispos. 2023 Jun;51(6):782-791. doi: 10.1124/dmd.123.001257. Epub 2023 Mar 15. PMID: 36921993. 11: Dreyer R, Pfukwa R, Barth S, Hunter R, Klumperman B. The Evolution of SNAP- Tag Labels. Biomacromolecules. 2023 Feb 13;24(2):517-530. doi: 10.1021/acs.biomac.2c01238. Epub 2023 Jan 6. PMID: 36607253. 12: Fu J, Lv Y, Jia Q, Wang C, Wang S, Liang P, Han S, He L. Purification and determination of antibody drugs in bio-samples by EGFR/cell membrane chromatography method. J Pharm Biomed Anal. 2022 Aug 5;217:114808. doi: 10.1016/j.jpba.2022.114808. Epub 2022 Apr 29. PMID: 35569271. 13: Chen YX, He LL, Xiang XP, Shen J, Qi HY. O6-methylguanine DNA methyltransferase is upregulated in malignant transformation of gastric epithelial cells via its gene promoter DNA hypomethylation. World J Gastrointest Oncol. 2022 Mar 15;14(3):664-677. doi: 10.4251/wjgo.v14.i3.664. PMID: 35321285; PMCID: PMC8919019. 14: Zhang Y, Han L, Tian X, Peng C, Chen Y. Ligand-Directed Caging Enables the Control of Endogenous DNA Alkyltransferase Activity with Light inside Live Cells. Angew Chem Int Ed Engl. 2022 Apr 19;61(17):e202115472. doi: 10.1002/anie.202115472. Epub 2022 Mar 4. PMID: 35199422. 15: Liang S, Xu H, Ye BC. Membrane-Decorated Exosomes for Combination Drug Delivery and Improved Glioma Therapy. Langmuir. 2022 Jan 11;38(1):299-308. doi: 10.1021/acs.langmuir.1c02500. Epub 2021 Dec 22. PMID: 34936368. 16: Franco Pinto J, Fillion A, Duchambon P, Bombard S, Granzhan A. Acridine-O6-benzylguanine hybrids: Synthesis, DNA binding, MGMT inhibition and antiproliferative activity. 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