Basic information
- CAS
148504-34-1- Standard SMILES
CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)Cc1cc2c(cc1OC(C)=O)Oc1cc(OC(C)=O)c(CN(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O)cc1C21OC(=O)c2ccccc21- InChIKey
BQRGNLJZBFXNCZ-UHFFFAOYSA-N- Molecular formula
- C46H46N2O23
- Average molar mass
- 994.9 g/mol
- Monoisotopic mass
- 994.24913572
Overview
Calcein am is an organic heteropentacyclic compound that is calcein in which all four carboxy group hydrogens have been substituted by (acetyloxy)methoxy groups and the hyrodgens of the two hydroxy groups have been substituted by acetyl groups. It is a a non-fluorescent probe cleaved to a fluorescent probe by non-specific intracellular esterases. It has a role as a fluorochrome. It is a gamma-lactone, a xanthene dye, an oxaspiro compound, an organic heteropentacyclic compound, a member of 2-benzofurans and an acetate ester. It is functionally related to a calcein.
Names & identifiers
- Preferred name
- calcein AM
- IUPAC
- acetyloxymethyl 2-[[2-(acetyloxymethoxy)-2-oxoethyl]-[[3',6'-diacetyloxy-7'-[[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]methyl]-3-oxospiro[2-benzofuran-1,9'-xanthene]-2'-yl]methyl]amino]acetate
- English name
- CALCEIN-AM
- Molecular formula
- C46H46N2O23
- Molecular weight
- 994.86
Names & synonyms
Calcein AM148504-34-1calcein-acetoxymethyl esteracetoxymethyl 2-[[2-(acetoxymethoxy)-2-oxo-ethyl]-[[3',6'-diacetoxy-7'-[[bis[2-(acetoxymethoxy)-2-oxo-ethyl]amino]methyl]-3-oxo-spiro[isobenzofuran-1,9'-xanthene]-2'-yl]methyl]amino]acetateDTXSID101043565CHEBI:3303acetoxymethyl 2-((2-(acetoxymethoxy)-2-oxo-ethyl)-((3',6'-diacetoxy-7'-((bis(2-(acetoxymethoxy)-2-oxo-ethyl)amino)methyl)-3-oxo-spiro(isobenzofuran-1,9'-xanthene)-2'-yl)methyl)amino)acetateRefChem:122727DTXCID601526081Glycine, N,N'-((3',6'-bis(acetyloxy)-3-oxospiro(isobenzofuran-1(3H),9'-(9H)xanthene)-2',7'-diyl)bis(methylene))bis(N-(2-((acetyloxy)methoxy)-2-oxoethyl))-, bis((acetyloxy)methyl) estercalcein-AMCalcein, AM
Show more names
Calcein AcetoxyMethyl EsterCAL-AMNSC 689290AM /Calcein-AMCAL-AMCalcein AM solutionCellstain- Calcein-AM-Cellstain-Calcein-AmSolutionCalcein, AM *CAS 148504-34-1*
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 305 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 25
- Rotatable bonds
- 32
- Heavy atoms
- 71
- Formal charge
- 0
- Complexity
- 1,810
Physicochemical properties
- Melting point
- 250 ℃ · >250℃
- Boiling point
- 982.7 · 982.7±65.0 °C(Predicted)
- Density
- 1.49 · 1.49±0.1 g/cm3(Predicted)
- refractive index
- 20 · n20/D 1.479
- Flash point
- 85 °C · 85 °C
- storage temp.
- -20 °C · -20°C
- solubility
- 10 mg/mL, · DMSO: soluble10mg/mL, clear, colorless to slightly yellow
- form
- powder
- pka
- 2.66 · 2.66±0.50(Predicted)
- color
- Colorless
- Appearance
- Solid Powder
- λmax
- 300 nm · < 300 nm
- Biological Applications
- Calcium indicators; zinc indicators; cytotoxicity assays; apoptosis assays; viability assays; labile iron pool assays; chemotaxis probes; cell adhesion probes; mitochondrial probes; P-glycoprotein probes;multi-drug resistance probes;treating atherosclerosis,cancer;ischemic disease
- InChIKey
- BQRGNLJZBFXNCZ-UHFFFAOYSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10-21
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- ridadr
- NA 1993 / PGIII
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.
Applications
DescriptionCalcein AM is a non-fluorescent, cell-permeable derivative of calcein, a self-quenching fluorescent dye. Calcein AM can be cleaved to release calcein in cells. Calcein is used as a substrate for multidrug resistance-associated protein 1 (MRP1) and multidrug resistance protein 3 (MDR3, P-glycoprotein 3).
UsesCalcein-AM appears to best satisfy the criteria for assaying cell adhesion and to have the least effect on cell viability and cell functions.
UsesCalcein-AM is a hydrophobic non-fluorescent probe that can permeate the plasma membrane and can be hydrolyzed to Calcein (sc-202090), which is an extremely fluorescent and negatively charged molecule. Calcein-AM can be used to stain living cells and in cytoplasmic Schwann cells has been observed to fluoresce bright green. Calcein-AM has been reported to be a neutral substrate for P-glycoprotein (Pgp) and multidrug resistance protein (MRP) and has been used in flow cytometry studies to analyze the function of P-gp and MRP.
UsesA non-fluorescent, membrane permeable probe that can be hydrolyzed to a fluorescent molecule
General DescriptionLiposomes contain a self-quenching fluorescent dye called calcein. It is a fluorescent dye with excitation and emission wavelengths of 495/515 nm, respectively. It self-quenches at concentrations above 70mM and is commonly used as an indicator of lipid vesicle leakage. The leakage rate is calculated on the basis of the fluorescence increment as the entrapped calcein is leaked out of the liposomal compartment. It is used as a complexometric indicator for titration of calcium ions with EDTA, and for fluorometric determination of calcium.
Related reactions
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Compound notes
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