Date published: 2025-10-17

1-800-457-3801

SCBT Portrait Logo
Seach Input

O6-Benzylguanine (CAS 19916-73-5)

5.0(1)
Write a reviewAsk a question

See product citations (7)

Alternate Names:
6-O-Benzylguanine; 2-Amino-6-(benzyloxy)purine
Application:
O6-Benzylguanine is an effective substrate and efficient inactivator of DNA alkyltransferase
CAS Number:
19916-73-5
Purity:
≥98%
Molecular Weight:
241.2
Molecular Formula:
C12H11N5O
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

QUICK LINKS

O6-Benzylguanine (O6-BG) is a highly versatile organobenzylguanine derivative extensively utilized in organic synthesis, biochemistry, and molecular biology. This compound serves multiple purposes, including guanine derivative synthesis, DNA methyltransferase inhibition, and protein-protein interaction studies. As a potent and selective inhibitor, O6-Benzylguanine targets DNA methyltransferases (DNMTs), enzymes involved in epigenetic gene expression regulation. Furthermore, O6-Benzylguanine facilitates the investigation of protein-protein interactions by binding to proteins and inducing conformational changes. It finds utility in in vitro and in vivo experiments to explore the impact of epigenetic regulation on gene expression. Although the precise mechanism of action of O6-Benzylguanine remains incompletely understood, it is believed to hinder DNMTs by binding to their active sites and impeding the transfer of methyl groups, thereby inhibiting enzyme activity. Notably, O6-Benzylguanine exhibits diverse biochemical and physiological effects. It inhibits DNMT activity, leading to alterations in gene expression. Additionally, O6-Benzylguanine influences the activity of various proteins, influencing metabolic pathways, as well as the production of proteins and hormones. Moreover, O6-Benzylguanine has demonstrated anti-inflammatory, anti-cancer, and anti-viral properties in vitro.


O6-Benzylguanine (CAS 19916-73-5) References

  1. Prolonged inhibition of O(6)-methylguanine DNA methyltransferase in human tumor cells by O(6)-benzylguanine in vitro and in vivo.  |  Kreklau, EL., et al. 1999. J Pharmacol Exp Ther. 291: 1269-75. PMID: 10565851
  2. O6-benzylguanine-mediated enhancement of chemotherapy.  |  Friedman, HS., et al. 2002. Mol Cancer Ther. 1: 943-8. PMID: 12481416
  3. Depletion of O6-alkylguanine-DNA alkyltransferase by O6-benzylguanine in three-dimensional collagen cultures of normal human breast epithelial cells.  |  Hamdan, MA., et al. 1992. Carcinogenesis. 13: 1743-9. PMID: 1423833
  4. Beta-glucuronidase-cleavable prodrugs of O6-benzylguanine and O6-benzyl-2'-deoxyguanosine.  |  Wei, G., et al. 2005. J Med Chem. 48: 256-61. PMID: 15634019
  5. O6-methylguanine-DNA methyltransferase, O6-benzylguanine, and resistance to clinical alkylators in pediatric primary brain tumor cell lines.  |  Bobola, MS., et al. 2005. Clin Cancer Res. 11: 2747-55. PMID: 15814657
  6. The O6-methyguanine-DNA methyltransferase inhibitor O6-benzylguanine enhanced activity of temozolomide + irinotecan against models of high-risk neuroblastoma.  |  Hindle, A., et al. 2021. Anticancer Drugs. 32: 233-247. PMID: 33323683
  7. Human liver oxidative metabolism of O6-benzylguanine.  |  Roy, SK., et al. 1995. Biochem Pharmacol. 50: 1385-9. PMID: 7503788
  8. Biodistribution of O6-benzylguanine and its effectiveness against human brain tumor xenografts when given in polyethylene glycol or cremophor-EL.  |  Dolan, ME., et al. 1994. Cancer Chemother Pharmacol. 35: 121-6. PMID: 7987987
  9. Activation of human O6-alkylguanine-DNA alkyltransferase by DNA.  |  Goodtzova, K., et al. 1994. Biochemistry. 33: 8385-90. PMID: 8031773
  10. Differential inactivation of mammalian and Escherichia coli O6-alkylguanine-DNA alkyltransferases by O6-benzylguanine.  |  Elder, RH., et al. 1994. Biochem J. 298 (Pt 1): 231-5. PMID: 8129725
  11. O6-ethylguanine and O6-benzylguanine incorporated site-specifically in codon 12 of the rat H-ras gene induce semi-targeted as well as targeted mutations in Rat4 cells.  |  Bishop, RE., et al. 1996. Carcinogenesis. 17: 849-56. PMID: 8625500
  12. Pharmacokinetics of O6-benzylguanine in rats and its metabolism by rat liver microsomes.  |  Roy, SK., et al. 1995. Drug Metab Dispos. 23: 1394-9. PMID: 8689950
  13. O6-benzylguanine potentiates the in vivo toxicity and clastogenicity of temozolomide and BCNU in mouse bone marrow.  |  Chinnasamy, N., et al. 1997. Blood. 89: 1566-73. PMID: 9057638
  14. Reaction of O6-benzylguanine-resistant mutants of human O6-alkylguanine-DNA alkyltransferase with O6-benzylguanine in oligodeoxyribonucleotides.  |  Pegg, AE., et al. 1998. J Biol Chem. 273: 10863-7. PMID: 9556560
  15. O6-benzylguanine and its role in chemotherapy.  |  Dolan, ME. and Pegg, AE. 1997. Clin Cancer Res. 3: 837-47. PMID: 9815757

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

O6-Benzylguanine, 10 mg

sc-202747
10 mg
$50.00

O6-Benzylguanine, 50 mg

sc-202747A
50 mg
$77.00

How should this chemical be stored, once it is in a solution with methanol? 

Asked by: two2igm05
Thank you for your question. The solution should be tightly sealed and stored at -20 degrees Celsius; it is recommended to be used as soon as possible. Please contact Technical Service if you have further questions concerning this product.
Answered by: Tech Service 9
Date published: 2016-12-16
  • y_2025, m_10, d_14, h_6CST
  • bvseo_bulk, prod_bvqa, vn_bulk_3.0.42
  • cp_1, bvpage1
  • co_hasquestionsanswers, tq_1
  • loc_en_US, sid_202747, prod, sort_[SortEntry(order=LAST_APPROVED_ANSWER_SUBMISSION_TIME, direction=DESCENDING)]
  • clientName_scbt
  • bvseo_sdk, java_sdk, bvseo-4.0.0
  • CLOUD, getContent, 98ms
  • QUESTIONS, PRODUCT
Rated 5 out of 5 by from Kreklau et alKreklau et al. (PubMed ID 10565851) found that O6-Benzylguanine blocked methylguanine DNA methyltransferase (MGMT) activity in tumor cells and xenograft tumors. -SCBT Publication Review
Date published: 2015-06-02
  • y_2025, m_10, d_14, h_6
  • bvseo_bulk, prod_bvrr, vn_bulk_3.0.42
  • cp_1, bvpage1
  • co_hasreviews, tv_0, tr_1
  • loc_en_US, sid_202747, prod, sort_[SortEntry(order=SUBMISSION_TIME, direction=DESCENDING)]
  • clientName_scbt
  • bvseo_sdk, java_sdk, bvseo-4.0.0
  • CLOUD, getReviews, 22ms
  • REVIEWS, PRODUCT
O6-Benzylguanine is rated 5.0 out of 5 by 1.
  • y_2025, m_10, d_14, h_6
  • bvseo_bulk, prod_bvrr, vn_bulk_3.0.42
  • cp_1, bvpage1
  • co_hasreviews, tv_0, tr_1
  • loc_en_US, sid_202747, prod, sort_[SortEntry(order=SUBMISSION_TIME, direction=DESCENDING)]
  • clientName_scbt
  • bvseo_sdk, java_sdk, bvseo-4.0.0
  • CLOUD, getAggregateRating, 113ms
  • REVIEWS, PRODUCT