Calcein

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Calcein_table_infobox_0

CalceinCalcein_table_caption_0
NamesCalcein_header_cell_0_0_0
IdentifiersCalcein_header_cell_0_1_0
CAS NumberCalcein_cell_0_2_0 Calcein_cell_0_2_1
3D model (JSmol)Calcein_cell_0_3_0 Calcein_cell_0_3_1
ChEBICalcein_cell_0_4_0 Calcein_cell_0_4_1
ChEMBLCalcein_cell_0_5_0 Calcein_cell_0_5_1
ChemSpiderCalcein_cell_0_6_0 Calcein_cell_0_6_1
ECHA InfoCardCalcein_cell_0_7_0 Q413006#P2566Calcein_cell_0_7_1
PubChem CIDCalcein_cell_0_8_0 Calcein_cell_0_8_1
CompTox Dashboard (EPA)Calcein_cell_0_9_0 Calcein_cell_0_9_1
PropertiesCalcein_header_cell_0_10_0
Chemical formulaCalcein_cell_0_11_0 C30H26N2O13Calcein_cell_0_11_1
Molar massCalcein_cell_0_12_0 622.53 g/molCalcein_cell_0_12_1
Melting pointCalcein_cell_0_13_0 DecomposesCalcein_cell_0_13_1
Boiling pointCalcein_cell_0_14_0 N/ACalcein_cell_0_14_1
Solubility in waterCalcein_cell_0_15_0 SlightlyCalcein_cell_0_15_1
Calcein_cell_0_16_0 Calcein_cell_0_16_1

Calcein, also known as fluorexon, fluorescein complex, is a fluorescent dye with and emission wavelengths of 495/515 nm, respectively, and has the appearance of orange crystals. Calcein_sentence_0

Calcein self-quenches at concentrations above 70mM and is commonly used as an indicator of lipid vesicle leakage. Calcein_sentence_1

It is also used traditionally as a complexometric indicator for titration of calcium ions with EDTA, and for fluorometric determination of calcium. Calcein_sentence_2

Applications Calcein_section_0

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. Calcein_sentence_3

Alternatively, Fura-2 , Furaptra , Indo-1 and aequorin may be used. Calcein_sentence_4

An acetomethoxy group obscures the part of the molecule that chelates Ca, Mg, Zn and other ions. Calcein_sentence_5

After transport into the cells, intracellular esterases remove the acetomethoxy group, the molecule gets trapped inside and gives out strong green fluorescence. Calcein_sentence_6

As dead cells lack active esterases, only live cells are labeled and counted by flow cytometry. Calcein_sentence_7

Calcein is now rarely used as a Ca or Mg indicator because its fluorescence is directly sensitive to these ions only at strongly alkaline pH, and thus it is not particularly useful for measuring Ca or Mg in cells. Calcein_sentence_8

Fluorescence of calcein is quenched strongly by Co, Ni and Cu and appreciably by Fe and Mn at physiological pH. Calcein_sentence_9

This fluorescence quenching response can be exploited for detecting the opening of the mitochondrial permeability transition pore (mPTP) and for measuring cell volume changes. Calcein_sentence_10

Calcein is commonly used for cell tracing and in studies of endocytosis, cell migration, and gap junctions. Calcein_sentence_11

The acetoxymethyl ester of calcein is also used to detect drug interactions with multidrug resistance proteins (ABC transporters ATP-binding cassette transporter genes) in intact cells as it is an excellent substrate of the multidrug resistance transporter 1 (MDR1) P-glycoprotein and the Multidrug Resistance-Associated Protein (MRP1). Calcein_sentence_12

The calcein AM assay can be used as a model for drug-drug interactions, for screening transporter substrates and/or inhibitors; and also to determine in vitro drug resistance of cells, including samples from patients. Calcein_sentence_13

Calcein is also used for marking freshly hatched fish and for labeling of bones in live animals. Calcein_sentence_14


Credits to the contents of this page go to the authors of the corresponding Wikipedia page: en.wikipedia.org/wiki/Calcein.