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calcein

Structure via PubChem · Public domain (PubChem)

EntityQ413006· pop 13· linked from 13 articles

Also known as N,N'-(3',6'-Dihydroxyspiro(phthalid-3,9'-xanthen)-2',7'-diyldimethyl)bis(iminodiessigsaeure), 2,7-Bis(N,N-bis(carboxymethyl)aminomethylene)fluorescein, 2',7'-Bis((bis(carboxymethyl)amino)methyl)fluorescein

Calcein, also known as fluorexon, fluorescein complex, is a fluorescent dye with excitation and emission wavelengths of 495 and 515 nm, respectively, and has the appearance of orange crystals. Calcein self-quenches at concentrations above 70 mM and is commonly used as an indicator of lipid vesicle leakage. It has also been traditionally used as a complexometric indicator for titration of calcium ions with EDTA, and for fluorometric determination of calcium.

Chemical data

Formula
C30H26N2O13
Molecular weight
622.5 g/mol
IUPAC name
2-[[7'-[[bis(carboxymethyl)amino]methyl]-3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-2'-yl]methyl-(carboxymethyl)amino]acetic acid
SMILES
C1=CC=C2C(=C1)C(=O)OC23C4=C(C=C(C(=C4)CN(CC(=O)O)CC(=O)O)O)OC5=C3C=C(C(=C5)O)CN(CC(=O)O)CC(=O)O
InChIKey
DEGAKNSWVGKMLS-UHFFFAOYSA-N
XLogP
-3.1
Polar surface area
232 Ų
H-bond donors
6
H-bond acceptors
15
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Phase 2
Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Has part
carbon
Mass
622.143
Show 5 more facts
Commons category
Calcein
chemical formula
C₃₀H₂₆N₂O₁₃
canonical SMILES
C1=CC=C2C(=C1)C(=O)OC23C4=CC(=C(C=C4OC5=CC(=C(C=C35)CN(CC(=O)O)CC(=O)O)O)O)CN(CC(=O)O)CC(=O)O
World Health Organisation international non-proprietary name
oftasceine
subject has role
fluorophore
Sources (3)

via Wikidata · CC0

~3 min read

Encyclopedic overview

2 sections
Contents
  • Applications
  • References

Calcein, also known as fluorexon, fluorescein complex, is a fluorescent dye with excitation and emission wavelengths of 495 and 515 nm, respectively, and has the appearance of orange crystals. Calcein self-quenches at concentrations above 70 mM and is commonly used as an indicator of lipid vesicle leakage. It has also been traditionally used as a complexometric indicator for titration of calcium ions with EDTA, and for fluorometric determination of calcium.

==Applications== thumbnail|After Calcein-AM is taken up into the cell, it is converted by esterases into calcein (below). This is capable of complexing calcium ions, resulting in a green fluorescence. Since only living cells possess sufficient esterases, only live cells fluoresce green after excitation The non-fluorescent acetomethoxy derivate of calcein (calcein AM, AM = acetoxymethyl) is used in biology as it can be transported through the cellular membrane into live cells, which makes it useful for testing of cell viability and for short-term labeling of cells. Alternatively, Fura-2, Furaptra, Indo-1 and aequorin may be used. An acetomethoxy group obscures the part of the molecule that chelates Ca2+, Mg2+, Zn2+ and other ions. After transport into the cells, intracellular esterases remove the acetomethoxy group, the molecule gets trapped inside and gives out strong green fluorescence. As dead cells lack active esterases, only live cells are labeled and counted by flow cytometry.

Excerpted from Wikipedia’s “calcein” article, available under the CC BY-SA 4.0 licence.

Gallery (3)