O6-Benzylguanine (Synonyms: NSC 637037) |
| Catalog No.GC13745 |
구아닌 유사체인 O6-벤질구아닌은 DNA 복구 효소 O6-알킬구아닌-DNA 알킬트랜스퍼라제(MGMT/AGT) 억제제입니다. O6-벤질구아닌은 AGT 기질로 작용하여 벤질 그룹을 AGT 시스테인 잔기로 전달하여 AGT를 비가역적으로 비활성화하고 DNA 복구를 방지합니다. O6-벤질구아닌은 종양 세포 사멸을 유도합니다. 항종양 활성.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 19916-73-5
Sample solution is provided at 25 µL, 10mM.
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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.
| Cas No. | 19916-73-5 | SDF | |
| Synonyms | NSC 637037 | ||
| 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 | 4°C, protect from light |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.1459 mL | 20.7297 mL | 41.4594 mL |
| 5 mM | 0.8292 mL | 4.1459 mL | 8.2919 mL |
| 10 mM | 0.4146 mL | 2.073 mL | 4.1459 mL |
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
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Quality Control & SDS
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- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 34 reference(s) in Google Scholar.)
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