Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H11N5O |
| Molecular Weight | 241.2486 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC2=C(N=CN2)C(OCC3=CC=CC=C3)=N1
InChI
InChIKey=KRWMERLEINMZFT-UHFFFAOYSA-N
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)
6-O-BENZYLGUANINE is a guanine analogue with antineoplastic activity. O(6)-benzylguanine binds the DNA repair enzyme O(6)-alkylguanine DNA alkyltransferase (AGT), transferring the benzyl moiety to the active-site cysteine and resulting in inhibition of AGT-mediated DNA repair. Co-administration of this agent potentiates the effects of other chemotherapeutic agents that damage DNA. 6-O-benzylguanine has been used in trials studying the treatment of HIV Infection, Adult Gliosarcoma, Adult Glioblastoma, Stage I Adult Hodgkin Lymphoma, and Stage II Adult Hodgkin Lymphoma, among others.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Stable differentiation and clonality of murine long-term hematopoiesis after extended reduced-intensity selection for MGMT P140K transgene expression. | 2007-09-15 |
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| A concise synthesis of the Pennsylvania Green fluorophore and labeling of intracellular targets with O6-benzylguanine derivatives. | 2007-09-13 |
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| O6-benzylguanine and BCNU in multiple myeloma: a phase II trial. | 2007-08 |
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| Gateways to clinical trials. | 2007-06 |
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| Depletion of O6-methylguanine-DNA methyltransferase by O6-benzylguanine enhances 5-FU cytotoxicity in colon and oral cancer cell lines. | 2007-06 |
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| Molecular basis of selectivity of nucleoside triphosphate incorporation opposite O6-benzylguanine by sulfolobus solfataricus DNA polymerase Dpo4: steady-state and pre-steady-state kinetics and x-ray crystallography of correct and incorrect pairing. | 2007-05-04 |
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| Gateways to clinical trials. | 2007-04 |
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| S-alkylthiolation of O6-methylguanine-DNA-methyltransferase (MGMT) to sensitize cancer cells to anticancer therapy. | 2007-03 |
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| Phase I trial of polifeprosan 20 with carmustine implant plus continuous infusion of intravenous O6-benzylguanine in adults with recurrent malignant glioma: new approaches to brain tumor therapy CNS consortium trial. | 2007-02-01 |
|
| A phase II trial of O6-benzylguanine and carmustine in patients with advanced soft tissue sarcoma. | 2006-11 |
|
| Inhibition of human glutathione transferases by multidrug resistance chemomodulators in vitro. | 2006-10 |
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| Gateways to clinical trials. | 2006-10 |
|
| A single cycle of treatment with temozolomide, alone or combined with O(6)-benzylguanine, induces strong chemoresistance in melanoma cell clones in vitro: role of O(6)-methylguanine-DNA methyltransferase and the mismatch repair system. | 2006-10 |
|
| Characterisation of a P140K mutant O6-methylguanine-DNA-methyltransferase (MGMT)-expressing transgenic mouse line with drug-selectable bone marrow. | 2006-09 |
|
| Evaluation of two novel tag-based labelling technologies for site-specific modification of proteins. | 2006-08-15 |
|
| Fluorophores for live cell imaging of AGT fusion proteins across the visible spectrum. | 2006-08 |
|
| Dual agent chemoprotection by retroviral co-expression of either MDR1 or MRP1 with the P140K mutant of O6-methylguanine-DNA-methyl transferase. | 2006-08 |
|
| Directed evolution of O6-alkylguanine-DNA alkyltransferase for applications in protein labeling. | 2006-07 |
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| Gateways to clinical trials. | 2006-06 |
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| Inactivation of O6-alkylguanine DNA alkyltransferase as a means to enhance chemotherapy. | 2006-06 |
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| Molecular imaging of alkylguanine-DNA alkyltransferase: further evaluation of radioiodinated derivatives of O6-benzylguanine. | 2006-04 |
|
| Multicistronic lentiviral vectors containing the FMDV 2A cleavage factor demonstrate robust expression of encoded genes at limiting MOI. | 2006-03-15 |
|
| Modulation of chemotherapy resistance in regional therapy: a novel therapeutic approach to advanced extremity melanoma using intra-arterial temozolomide in combination with systemic O6-benzylguanine. | 2006-03 |
|
| Polar, functionalized guanine-O6 derivatives resistant to repair by O6-alkylguanine-DNA alkyltransferase: implications for the design of DNA-modifying drugs. | 2006-03 |
|
| O6-methylguanine DNA methyltransferase and p53 status predict temozolomide sensitivity in human malignant glioma cells. | 2006-02 |
|
| Effect of chemotherapy-induced DNA repair on oncolytic herpes simplex viral replication. | 2006-01-04 |
|
| Differential competitive resistance to methylating versus chloroethylating agents among five O6-alkylguanine DNA alkyltransferases in human hematopoietic cells. | 2006-01 |
|
| The P140K mutant of human O(6)-methylguanine-DNA-methyltransferase (MGMT) confers resistance in vitro and in vivo to temozolomide in combination with the novel MGMT inactivator O(6)-(4-bromothenyl)guanine. | 2006-01 |
|
| Role of O6-alkylguanine-DNA alkyltransferase in protecting against 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU)-induced long-term toxicities. | 2005-12 |
|
| Phase II trial of the O6-alkylguanine DNA alkyltransferase inhibitor O6-benzylguanine and 1,3-bis(2-chloroethyl)-1-nitrosourea in advanced melanoma. | 2005-11-01 |
|
| [O6-benzylguanine stimulates regulatory functions of the Ada protein in Escherichia coli]. | 2005-11 |
|
| Role of O6-methylguanine-DNA methyltransferase and effect of O6-benzylguanine on the anti-tumor activity of cis-diaminedichloroplatinum(II) in oral cancer cell lines. | 2005-11 |
|
| Phase I study of O6-benzylguanine and temozolomide administered daily for 5 days to pediatric patients with solid tumors. | 2005-10-20 |
|
| Synthesis and preliminary biological evaluation of O6-[4-(2-[18F]fluoroethoxymethyl)benzyl]guanine as a novel potential PET probe for the DNA repair protein O6-alkylguanine-DNA alkyltransferase in cancer chemotherapy. | 2005-10-15 |
|
| Phase I trial of temozolomide plus O6-benzylguanine for patients with recurrent or progressive malignant glioma. | 2005-10-01 |
|
| Dose finding and O6-alkylguanine-DNA alkyltransferase study of cisplatin combined with temozolomide in paediatric solid malignancies. | 2005-09-05 |
|
| Substituted purine analogues define a novel structural class of catalytic topoisomerase II inhibitors. | 2005-08-15 |
|
| O6-methylguanine-DNA methyltransferase, O6-benzylguanine, and resistance to clinical alkylators in pediatric primary brain tumor cell lines. | 2005-04-01 |
|
| Role of glutathione and nucleotide excision repair in modulation of cisplatin activity with O6-benzylguanine. | 2005-04 |
|
| Inactivated MGMT by O6-benzylguanine is associated with prolonged G2/M arrest in cancer cells treated with BCNU. | 2005-03-24 |
|
| Polyclonal chemoprotection against temozolomide in a large-animal model of drug resistance gene therapy. | 2005-02-01 |
|
| Beta-glucuronidase-cleavable prodrugs of O6-benzylguanine and O6-benzyl-2'-deoxyguanosine. | 2005-01-13 |
|
| The antineoplastic efficacy of the prodrug Cloretazine is produced by the synergistic interaction of carbamoylating and alkylating products of its activation. | 2005 |
|
| Synthesis and antitumor activity of methyltriazene prodrugs simultaneously releasing DNA-methylating agents and the antiresistance drug O(6)-benzylguanine. | 2004-12-30 |
|
| Hematopoietic stem cell gene therapy of murine protoporphyria by methylguanine-DNA-methyltransferase-mediated in vivo drug selection. | 2004-11 |
|
| Gateways to clinical trials. | 2004-09 |
|
| Brain tumor cell lines resistant to O6-benzylguanine/1,3-bis(2-chloroethyl)-1-nitrosourea chemotherapy have O6-alkylguanine-DNA alkyltransferase mutations. | 2004-09 |
|
| Lentivirus-mediated expression of mutant MGMTP140K protects human CD34+ cells against the combined toxicity of O6-benzylguanine and 1,3-bis(2-chloroethyl)-nitrosourea or temozolomide. | 2004-08 |
|
| 2-amino-O4-benzylpteridine derivatives: potent inactivators of O6-alkylguanine-DNA alkyltransferase. | 2004-07-15 |
|
| Gateways to clinical trials. | 2004-05 |
Sample Use Guides
Cutaneous T-cell lymphoma: Treatment once every 2 weeks with 120 mg/m(2) intravenous O6-benzylguanine followed 1 hour later by whole-body, low-dose topical carmustine starting at 10 mg, with 10-mg incremental dose-escalation in 3 patient cohorts.
Route of Administration:
Intravenous
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NCI_THESAURUS |
C2134
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SUB35463
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01KC87F8FE
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100000128431
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DTXSID20173700
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C1306
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DB11919
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637037
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4578
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19916-73-5
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O6-BENZYLGUANINE
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ACTIVE MOIETY
