Calcein-AM

SKU: C0009

Category: Fluorescent Detection

Synonyms: Calcein O,O'-diacetate tetrakis(acetoxymethyl) ester , Calcein acetoxymethyl ester , Diacetate , CAL-AM , NSC 689290; 148504-34-1
CAS-Number: C₄₆H₄₆N₂O₂₃
Molecular Formula: 994.86
Molecular Weight

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥95% (HPLC)
Appearance: White to off-white solid

Properties

Solvents: DMSO

Long Term Storage: -20°C
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.
Handling Advice: Protect from light and moisture.
Short Term Storage: -20°C
Shipping: BLUE ICE

Transportation: Not dangerous goods

Description: Calcein AM is a non-fluorescent cell permeable and hydrophobic probe that, upon entering live cells, is cleaved by intracellular esterases, releasing the membrane-impermeable, hydrophilic, and intensely bright green fluorescent calcein. Better retained by viable cells than fluorescein, carboxyfluorescein, or BCECF, due to its low cytotoxicity. It can be used as an indicator of cell viability (dead cells lack cytoplasmic esterases), cell-cell communication, cytotoxicity or changes in intracellular calcium, fluoride, iron or mercury. Calcein-AM is a neutral substrate for multidrug resistance-associated protein 1 (MRP1) and multidrug resistance protein 3 (MDR3, P-glycoprotein 3) and has been used in flow cytometry studies to analyze the function of P-gp and MRP. Used as a cytosolic fluorophore in mitochondrial permeability studies to image pore transition. Viability assays using calcein are reliable and correlate well with the standard 51Cr-release assay. Spectral Data: λex 496nm, λem 516nm in 0.1M Tris pH 8.0.
InChi: 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
References: (1) N. Feller, et al., Br. J. Cancer. 72, 543 (1995) , (2) N. Feller, et al., FEBS Lett. 368 385 (1995) , (3) F. Tiberghien & F. Loor, Anti-Cancer Drugs 7, 568 (1996) , (4) P. Decherchi, et al., J. Neurosci. Methods 71, 205 (1997) , (5) M. Essodaigui, et al., Biochemistry 37, 2243 (1998) , (6) J.J. Lemasters, et al., Biochim. Biophys. Acta. 1366, 177 (1998) , (7) J. Hynes, et al., J. Biomol. Screen. 8, 264 (2003) , (8) D. Bratosin, et al., Cytometry A 66, 78 (2005) , (9) R.W. Sabnis, Handbook of biological dyes and stains (2010) , (10) G. Szakacs, et al., Pathol. Oncol. Res. 4, 251 (2016)
InChi Key: XKFSBWQWNMZWFA-UHFFFAOYSA-N
Smiles: O=C(C1=C2C=CC=C1)OC32C4=C(C(CN(CC(OCOC(C)=O)=O)CC(OCOC(C)=O)=O)=C(OC(C)=O)C=C4)OC5=C(CN(CC(OCOC(C)=O)=O)CC(OCOC(C)=O)=O)C(OC(C)=O)=CC=C53

Calcein AM is a non-fluorescent cell permeable and hydrophobic probe that, upon entering live cells, is cleaved by intracellular esterases, releasing the membrane-impermeable, hydrophilic, and intensely bright green fluorescent calcein. Better retained by viable cells than fluorescein, carboxyfluorescein, or BCECF, due to its low cytotoxicity. It can be used as an indicator of cell viability (dead cells lack cytoplasmic esterases), cell-cell communication, cytotoxicity or changes in intracellular calcium, fluoride, iron or mercury. Calcein-AM is a neutral substrate for multidrug resistance-associated protein 1 (MRP1) and multidrug resistance protein 3 (MDR3, P-glycoprotein 3) and has been used in flow cytometry studies to analyze the function of P-gp and MRP. Used as a cytosolic fluorophore in mitochondrial permeability studies to image pore transition. Viability assays using calcein are reliable and correlate well with the standard 51Cr-release assay. Spectral Data: λex 496nm, λem 516nm in 0.1M Tris pH 8.0.

SKU: C0009 Category: Fluorescent Detection

Additional information

Additional information

Synonyms	Calcein O,O'-diacetate tetrakis(acetoxymethyl) ester, Calcein acetoxymethyl ester, Diacetate, CAL-AM, NSC 689290
Purity	≥95% (HPLC)
Appearance	White to off-white solid
CAS-Number	148504-34-1
Molecular Formula	C46H46N2O23
Molecular Weight	994.86
Solvents	DMSO
Smiles	O=C(C1=C2C=CC=C1)OC32C4=C(C(CN(CC(OCOC(C)=O)=O)CC(OCOC(C)=O)=O)=C(OC(C)=O)C=C4)OC5=C(CN(CC(OCOC(C)=O)=O)CC(OCOC(C)=O)=O)C(OC(C)=O)=CC=C53
InChi Key	XKFSBWQWNMZWFA-UHFFFAOYSA-N
Shipping	BLUE ICE
Short Term Storage	-20°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Transportation	Not dangerous goods
References	(1) N. Feller, et al., Br. J. Cancer. 72, 543 (1995), (2) N. Feller, et al., FEBS Lett. 368 385 (1995), (3) F. Tiberghien & F. Loor, Anti-Cancer Drugs 7, 568 (1996), (4) P. Decherchi, et al., J. Neurosci. Methods 71, 205 (1997), (5) M. Essodaigui, et al., Biochemistry 37, 2243 (1998), (6) J.J. Lemasters, et al., Biochim. Biophys. Acta. 1366, 177 (1998), (7) J. Hynes, et al., J. Biomol. Screen. 8, 264 (2003), (8) D. Bratosin, et al., Cytometry A 66, 78 (2005), (9) R.W. Sabnis, Handbook of biological dyes and stains (2010), (10) G. Szakacs, et al., Pathol. Oncol. Res. 4, 251 (2016)
InChi	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
Quantity	1 mg, Bulk