SML1690
ASMI
≥98% (HPLC)
Synonym(s):
(E)-4-(4-(Acryloyloxy)styryl)-1-methylpyridinium iodide
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About This Item
Empirical Formula (Hill Notation):
C17H16NIO2
CAS Number:
Molecular Weight:
393.22
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 10 mg/mL, clear
storage temp.
2-8°C
SMILES string
C=CC(OC1=CC=C(C=C1)/C=C/C(C=C2)=CC=[N+]2C)=O.[I-]
Biochem/physiol Actions
ASMI is a cell-permeable, non-toxic, biocompatible, photostable, positively charged, mitochondria targeting styryl-methylpyridinium based compound that acts as a rapid, cysteine selective, sensitive, and ratiometric (F 518 /F 452 nm) fluorescent turn-on probe (0.5 - 40 μM of [Cys]). Under physiological conditions, cysteine thiol reacts with the ASMI acrylate moiety in a time-dependent manner, and induces a facile intramolecular cyclization to release fluorogenic oxystyryl methylpyridinium. ASMI displays high selectivity over other biothiols (Kobs = 0.75, 0.038, 0.011 & 0.012 min -1 for Cys, Hcy, GSH & Na 2 S, respectively) and with no interference from other biologically relevant amino acids, essential metal ions, and anions, including Na2S. Shown to monitor mitochondrial Cys levels in HeLa cells and in deep tissues (150 μm of penetration depth) by two-photon excited fluorescence microscopy.
Biocompatible, mitochondria localizing, ratiometric two-photon fluorescent sensing probe that selectively monitors Cys levels in living cells and in deep tissues
signalword
Warning
hcodes
pcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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