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
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About This Item
Empirical Formula (Hill Notation):
C16H14BrN5 · xHCl
Molecular Weight:
356.22 (free base basis)
UNSPSC Code:
41116158
NACRES:
NA.77
Assay:
≥95% (HPLC)
Form:
powder
Storage condition:
desiccated
Quality Segment
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
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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