Calcein-AM

Name: Calcein-AM
Brand: SIGMA

Small Package (20 X 50 μg ), ≥90.0% (HPLC)

Synonym(s):

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

NACRES:

NA.32

PubChem Substance ID:

329758218

UNSPSC Code:

12171500

MDL number:

MFCD05861516

Product Name

Calcein-AM, Small Package (20 X 50 μg ), ≥90.0% (HPLC)

InChI key

XKFSBWQWNMZWFA-UHFFFAOYSA-N

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

assay

≥90.0% (HPLC)

fluorescence

λ_ex 496 nm; λ_em 516 nm±5 nm in 0.1 M Tris pH 8.0, esterase; Ca²⁺

storage temp.

−20°C

Quality Level

100

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Clinical & Diagnostics

Dry Dyes & Certified Stains

Tissue Diagnostics

Application

Calcein-AM is used as a cell viability stain and as a neutral substrate for multidrug (MDR) efflux transporters. In cancer research, it is used as a neutral substrate for multidrug resistance protein MRP. Fluorescence assays to determine human erythrocyte viability and aging uses Calcein-AM as a probe.

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.

General description

Calcein-AM, also known as Calcein-acetoxymethyl ester, is a non-fluorescent molecule converted into an anionic fluorescent form by intracellular esterase enzymes. It provides a continuous visualization of adherent cells during the experiment. Calcein-AM is a vital dye that introduces Calcein in living cells with intact cell membranes. The fluorescent part of Calcein-AM localizes in the intracellular spaces after esterase-dependent cellular trapping, displaying cytotoxic activity in cells.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Cytotoxic activity of calcein acetoxymethyl ester (Calcein/AM) on primary cultures of human haematological and solid tumours.

B Jonsson et al.

European journal of cancer (Oxford, England : 1990), 32A(5), 883-887 (1996-05-01)

The aim of this study was to determine the in vitro cytotoxicity of calcein acetoxymethyl ester (Calcein/AM) on primary cultures derived from solid and haematological human tumours. Calcein/AM is a fluorescent dye that localises intracellularly after esterase-dependent cellular trapping and

Calcein-AM is a detector of intracellular oxidative activity.

Jacopo Uggeri et al.

Histochemistry and cell biology, 122(5), 499-505 (2004-10-27)

Calcein-acetoxymethylester (calcein-AM) is a non-fluorescent, cell permeant compound, which is converted by intracellular esterases into calcein, an anionic fluorescent form. It is used in microscopy and fluorometry and provides both morphological and functional information of viable cells. In this study

Novel fluorescence assay using calcein-AM for the determination of human erythrocyte viability and aging.

Daniela Bratosin et al.

Cytometry. Part A : the journal of the International Society for Analytical Cytology, 66(1), 78-84 (2005-05-26)

A highly sensitive, fast, and simple flow cytometric assay to assess human red blood cell (RBCs) viability and aging is reported. The assay described in this report is based on the use of acetoxymethyl ester of calcein (calcein-AM), a fluorescein

Parguerenes: Marine red alga bromoditerpenes as inhibitors of P-glycoprotein (ABCB1) in multidrug resistant human cancer cells.

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

Graft of the gelatin sponge scaffold containing genetically-modified neural stem cells promotes cell differentiation, axon regeneration, and functional recovery in rat with spinal cord transection.

Bao-Ling Du et al.

Journal of biomedical materials research. Part A, 103(4), 1533-1545 (2014-07-22)

Biological materials combined with genetically-modified neural stem cells (NSCs) are candidate therapy targeting spinal cord injury (SCI). Based on our previous studies, here we performed gelatin sponge (GS) scaffold seeded with neurotrophin-3 (NT-3) and its receptor TrkC gene modifying NSCs

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