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Sigma-Aldrich

Calcein-AM

BioReagent, suitable for fluorescence, ≥95.0% (HPLC)

Synonym(s):

Calcein acetoxymethyl ester, Calcein O,O′-diacetate tetrakis(acetoxymethyl) ester

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About This Item

Empirical Formula (Hill Notation):
C46H46N2O23
CAS Number:
148504-34-1
Molecular Weight:
994.86
MDL number:
MFCD05861516
UNSPSC Code:
12352200
PubChem Substance ID:
57647670
NACRES:
NA.32

product line

BioReagent

Quality Level

100

assay

≥95.0% (HPLC)

fluorescence

λex 496 nm; λem 516 nm in 0.1 M Tris pH 8.0, esterase; Ca2+

suitability

suitable for fluorescence

storage temp.

−20°C

SMILES string

CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)Cc1c(OC(C)=O)ccc2c1Oc3c(CN(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O)c(OC(C)=O)ccc3C24OC(=O)c5ccccc45

InChI

1S/C46H46N2O23/c1-25(49)60-21-64-39(55)17-47(18-40(56)65-22-61-26(2)50)15-32-37(68-29(5)53)13-11-35-43(32)70-44-33(16-48(19-41(57)66-23-62-27(3)51)20-42(58)67-24-63-28(4)52)38(69-30(6)54)14-12-36(44)46(35)34-10-8-7-9-31(34)45(59)71-46/h7-14H,15-24H2,1-6H3

InChI key

XKFSBWQWNMZWFA-UHFFFAOYSA-N

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General description

Liposomes 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.

Application

Calcein-AM has been used in flow cytometry.
Non-fluorescent cell permeable derivative of calcein, becomes fluorescent on hydrolysis. Used as a neutral substrate for multidrug resistance protein, MRP; employed in tumor research.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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T M Allen et al.
Biochimica et biophysica acta, 597(2), 418-426 (1980-04-10)
Efflux of contents from small unilamellar vesicles of various compositions, conaining a highly quenched fluorescent compound (calcein, 175 mM) was determined as a function of temperature in the presence and absence of human serum. Efflux of calcein from the liposomes
Y S Tsao et al.
Biochemistry, 24(5), 1092-1098 (1985-02-26)
Sendai virus induced liposome leakage has been studied by using liposomes containing a self-quenching fluorescent dye, calcein. The liposomes used in this study were prepared by a freeze and thaw method and were composed of phosphatidylcholine, phosphatidylserine, and phosphatidylethanolamine (1:2.60:1.48
Xiao-Cong Huang et al.
Biochemical pharmacology, 85(9), 1257-1268 (2013-02-19)
High intrinsic or acquired expression of membrane spanning, adenosine triphosphate binding cassette (ABC) transporter proteins, such as P-glycoprotein (P-gp), in cancers represents a major impediment to chemotherapy, with accelerated drug efflux leading to multi-drug resistance (MDR). Although ABC transporter inhibitors
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Journal of biomedical materials research. Part A, 103(4), 1533-1545 (2014-07-22)
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