| O6-BenzylguaninePotent MGMT inhibitor |
Sample solution is provided at 25 µL, 10mM.
Nature.2017 Jan 19;541(7637):417-420.
Nature.2018 Nov;563(7731):407-411.Nature.2018 Jun 13.Nature.2018 Jun 27.Nature.2018 Mar 29;555(7698):673-677.Nature.2017 Sep 7;549(7670):96-100.Nature.2016 Apr 21;532(7599):398-401.
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- Purity = 99.32%
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| Cas No. | 19916-73-5 | SDF | Download SDF |
| Chemical Name | 6-(benzyloxy)-9H-purin-2-amine | ||
| Canonical SMILES | [H]N1C2=NC(N)=NC(OCC3=CC=CC=C3)=C2N=C1 | ||
| Formula | C12H11N5O | M.Wt | 241.2 |
| Solubility | ≥11.3mg/mL in Ethano with gentle warming | Storage | Store at -20°C |
| Physical Appearance | A solid | Shipping Condition | Evaluation sample solution : ship with blue ice.All other available size:ship with RT , or blue ice upon request |
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. | ||
O6-Benzylguanine (BG) is a potent inhibitor of MGMT and an antineoplastic agent [1].
O6-methylguanine DNA methyltransferase (MGMT, also known as O6-Alkylguanine-DNA alkyltransferase, or AGT) is a DNA repair protein that removes the alkyl group located on the O6-position of guanine from DNA and restores DNA integrity. MGMT is alkylated and irreversibly inactivated.
O6-Benzylguanine is a potent MGMT inhibitor. In HT29 cells, O6-Benzylguanine significantly reduced MGMT stability and the affinity of MGMT for DNA, increased its sensitivity to proteases. O6-Benzylguanine also increased the cytotoxic effect of alkylating agent BCNU [1]. In SF767 cells, BG (25 μM for 1 h) reduced >95% of MGMT activity, while 33% of the activity recovered within 24 h. When cells pretreated with BG (2.5 μM for 24 h) followed by the same low-dose treatment for 24 h completely depleted MGMT activity [2]. In HCT116 and HCT15 cells, treatment with BG and BCNU inactivated MGMT and arrested 70-80% of cells in G2/M phase in response to the DNA damages induced by BCNU [3].
In nude mice bearing SF767 human brain tumor xenografts, treatment with O6-Benzylguanine prior to BCNU significantly inhibited tumor growth as compared to BCNU alone [1]. In xenograft SF767 tumors, pre- and post-treatments (8 mg/kg over 24 h) combined with an i.p. bolus dose (80 mg/kg) of BG inhibited >95% of MGMT activity [2].
References:[1]. Dolan ME, Pegg AE. O6-benzylguanine and its role in chemotherapy. Clin Cancer Res, 1997, 3(6): 837-847.[2]. Kreklau EL, Kurpad C, Williams DA, et al. Prolonged inhibition of O(6)-methylguanine DNA methyltransferase in human tumor cells by O(6)-benzylguanine in vitro and in vivo. J Pharmacol Exp Ther, 1999, 291(3): 1269-1275.[3]. Yan L, Donze JR, Liu L. Inactivated MGMT by O6-benzylguanine is associated with prolonged G2/M arrest in cancer cells treated with BCNU. Oncogene, 2005, 24(13): 2175-2183.
