structure of o6-Benzylguanine

o6-Benzylguanine

CAS No.: 1000874-21-4
M. Wt: 241.249
M. Fa: C12H11N5O
InChI Key: KRWMERLEINMZFT-UHFFFAOYSA-N

Names and Identifiers of 1000874-21-4

CAS Number

1000874-21-4

EC Number

449-870-7

IUPAC Name

6-phenylmethoxy-7H-purin-2-amine

InChI

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)

InChIKey

KRWMERLEINMZFT-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)COC2=NC(=NC3=C2NC=N3)N

UNII

01KC87F8FE

Physical and chemical properties of 1000874-21-4

Boiling Point

621.4±63.0 °C at 760 mmHg

Density

1.4±0.1 g/cm3

Exact Mass

241.096359

Flash Point

329.6±33.7 °C

Index of Refraction

1.743

LogP

1.95

Molecular Formula

C12H11N5O

Molecular Weight

241.249

Solubility

35.9 [ug/mL] (The mean of the results at pH 7.4)

Vapour Pressure

0.0±1.8 mmHg at 25°C

Safety Information of 1000874-21-4

Pictograms

Signal Word

 Warning

Safety Data Sheet
Supports customized editing of SDS information and downloading in PDF documents.

Applications of 1000874-21-4

O6-Benzylguanine has several applications:

  • Cancer Treatment: It is primarily used in cancer therapy as an adjuvant to increase the effectiveness of alkylating agents.
  • Research Tool: The compound serves as a valuable tool in molecular biology for studying DNA repair mechanisms and enzyme function.
  • Fluorescent Labeling: Modified versions are utilized for labeling proteins and studying cellular processes through fluorescence microscopy.

Interaction Studies of 1000874-21-4

Interaction studies involving O6-benzylguanine focus on its binding affinity and specificity towards O6-alkylguanine-DNA alkyltransferase. Research indicates that mutations within the enzyme can affect its susceptibility to inhibition by O6-benzylguanine, providing insights into resistance mechanisms in cancer therapy. Additionally, studies have explored how structural modifications to O6-benzylguanine can enhance its binding properties and therapeutic potential.

Biological Activity of 1000874-21-4

The biological activity of O6-benzylguanine is primarily linked to its role as an inhibitor of DNA repair mechanisms. By inhibiting O6-alkylguanine-DNA alkyltransferase, it increases the susceptibility of cancer cells to DNA-damaging agents. This property makes it a valuable compound in cancer therapy, particularly in combination treatments where enhancing the effects of chemotherapy is desired. Additionally, studies have shown that O6-benzylguanine can induce apoptosis in resistant tumor cells by promoting DNA damage accumulation.