6-(4-(aminomethyl)benzyloxy)-9H-purin-2-amine

• CAS: 674799-96-3
• Catalog Number: ACM674799963
• Category: Main Products
• Molecular Weight: 270.29
• Molecular Formula: C13H14N6O
• Synonyms: O-[4-(Aminomethyl)benzyl]guanine
• Appearance: Light yellow solid

Case Study

Organelle-Specific Hydrogen Peroxide Imaging in Living Cells Using SNAP-Tag Fluorogenic Probes

Srikun, Duangkhae, et al. Journal of the American Chemical Society 132.12 (2010): 4455-4465.

Hydrogen peroxide serves dual roles in living systems as both a damaging oxidant and a critical signaling molecule, yet methods for detecting local H₂O₂ fluctuations within specific subcellular compartments have been lacking. Two hybrid small-molecule/protein reporter systems were developed that combine boronate-caged fluorophores with genetically targetable SNAP-tag protein labeling technology to enable organelle-specific peroxide sensing in live cells.
Experimental Protocol: Two SNAP-tag peroxide reporters were synthesized: SPG1 (synthesized from 6-(4-(aminomethyl)benzyloxy)-9H-purin-2-amine), bearing a benzylguanine recognition unit for cell-surface labeling, and SPG2, incorporating a chloropyrimidine substrate for intracellular targeting. Upon reaction with SNAP-tag fusion proteins, these probes form covalent adducts that remain non-fluorescent until H₂O₂-mediated boronate deprotection triggers a fluorescence turn-on. Spectroscopic characterization was performed in buffered solution at pH 7. Confocal microscopy was conducted on live human embryonic kidney cells expressing SNAP-tag fusions localized to the plasma membrane, nucleus, mitochondria, and endoplasmic reticulum.
Performance Evaluation: The SNAP-tag bioconjugates exhibited absorption maxima at 465 nm and emission maxima at 515 nm with quantum yields between 0.07 and 0.12. Exposure to 1 mM H₂O₂ triggered an approximately 32-fold fluorescence enhancement with a pseudo-first-order rate constant of 1.0 times 10^-3 s^-1. In live-cell imaging, SPG1 selectively labeled extracellular membrane targets while SPG2 efficiently penetrated cells for intracellular organelle labeling. Time-lapse confocal imaging following H₂O₂ stimulation demonstrated robust, localized fluorescence increases at each targeted subcellular compartment with minimal background staining, enabling simultaneous multi-organelle peroxide mapping in living cells.

Custom Q&A

What is the molecular formula of the compound described in the reference?

The molecular formula is C13H14N6O.

What are the synonyms for the compound?

The synonyms for the compound are 6-((4-(Aminomethyl)benzyl)oxy)-7H-purin-2-amine, 674799-96-3, O6-[4-(Aminomethyl)benzyl]guanine, and 6-[[4-(aminomethyl)phenyl]methoxy]-7H-purin-2-amine.

What is the molecular weight of the compound?

The molecular weight is 270.29 g/mol.

When was the compound created?

The compound was created on February 16, 2009.

When was the compound last modified?

The compound was last modified on October 21, 2023.

What is the IUPAC name of the compound?

The IUPAC name of the compound is 6-[[4-(aminomethyl)phenyl]methoxy]-7H-purin-2-amine.

What is the InChI of the compound?

The InChI of the compound is InChI=1S/C13H14N6O/c14-5-8-1-3-9(4-2-8)6-20-12-10-11(17-7-16-10)18-13(15)19-12/h1-4,7H,5-6,14H2,(H3,15,16,17,18,19).

What is the InChIKey of the compound?

The InChIKey of the compound is UINSGVKWAFJDPI-UHFFFAOYSA-N.

What is the Canonical SMILES of the compound?

The Canonical SMILES of the compound is C1=CC(=CC=C1CN)COC2=NC(=NC3=C2NC=N3)N.

What is the XLogP3 value of the compound?

The XLogP3 value of the compound is 0.1.