SML3351

Br-DAPI hydrochloride

≥95% (HPLC)

• Synonym(s): 2-[4-(Aminoiminomethyl)phenyl]-3-bromo-1H-indole-6-carboximidamide hydrochloride, 3-Bromo-2-(4-carbamimidoylphenyl)-1H-indole-6-carboximidamide
• Empirical Formula (Hill Notation): C₁₆H₁₄BrN₅ · xHCl
• Molecular Weight: 356.22 (free base basis)
• UNSPSC Code: 41116158
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥95% (HPLC)
• form: powder
• storage condition: desiccated
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear
• storage temp.: 2-8°C
• SMILES string: BrC1=C(NC2=CC(C(N)=N)=CC=C12)C3=CC=C(C=C3)C(N)=N
• InChI: 1S/C16H14BrN5/c17-13-11-6-5-10(16(20)21)7-12(11)22-14(13)8-1-3-9(4-2-8)15(18)19/h1-7,22H,(H3,18,19)(H3,20,21)
• InChI key: GSBXNZFEZFIMCS-UHFFFAOYSA-N

Description

Biochem/physiol Actions

Br-DAPI is a DAPI-derived DNA-binding photosensitizer that produces reactive oxygen species (ROS) upon irradiation, resulting in single/double stranded breaks of bound DNA. Light-induced viability reduction is observed among A549 cells treated with Br-DAPI (IC50 = 1.3 μM; 45 min treatment), but not DAPI (IC50 >64 μM) upon photosensitization (365 nm 15 mW/cm2, 4.5 J/cm2 fluence rate). Its high permeation in both Gram-negative and Gram-positive bacteria allows selective light-induced eradication of bacteria over mammalian cells at low concentration (IC50 = 0.29 μM/N99 E. coli and 0.5 μM/B. subtilis) and light intensity (5 min irradiation by 365 nm LED at 15 mW/cm2, 4.5 J/cm2).

DAPI-derived DNA-binding photosensitizer that allows light-induced cancer cell killing at high concetrations and selective bacteria eradication at low concentrations.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable