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343242-M

FLUO 3/AM

Name: FLUO 3/AM
Brand: MM

Membrane-permeable version of FLUO 3. Unlike all other Ca²⁺ indicators, FLUO 3/AM is non-fluorescent until it is hydrolyzed in the cell by cellular esterases. It is insensitive to Mg²⁺.

Synonym(s):

FLUO 3/AM, 1-[2-Amino-5-(2,7-dichloro-6-hydroxy-3-oxo-3H-xanthen-9-yl)]-2-(2ʹ-amino-5ʹ-methylphenoxy)ethane-N,N,Nʹ,Nʹ-tetraacetic Acid Pentaacetoxymethyl Ester

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About This Item

Empirical Formula (Hill Notation):

C₅₁H₅₀Cl₂N₂O₂₃

CAS Number:

121714-22-5

Molecular Weight:

1129.85

MDL number:

MFCD00083336

UNSPSC Code:

12171500

NACRES:

NA.77

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Properties

Quality Segment

100

assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

red-orange

solubility

DMSO: 5 mM, DMF: soluble

storage temp.

−20°C

SMILES string

Clc1[c](cc2[o]c3c(c(c2c1)c4cc(c(cc4)N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C)OCCOc5c(ccc(c5)C)N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C)cc(c(c3)OCOC(=O)C)Cl)=O

InChI

1S/C51H50Cl2N2O23/c1-28-7-9-39(54(19-47(62)74-24-69-30(3)57)20-48(63)75-25-70-31(4)58)45(13-28)66-11-12-67-46-14-34(8-10-40(46)55(21-49(64)76-26-71-32(5)59)22-50(65)77-27-72-33(6)60)51-35-15-37(52)41(61)17-42(35)78-43-18-44(38(53)16-36(43)51)73-23-68-29(2)56/h7-10,13-18H,11-12,19-27H2,1-6H3

InChI key

PTPUOMXKXCCSEN-UHFFFAOYSA-N

Description

General description

Membrane-permeable version of FLUO 3 (Cat. No. 343244). Cleavage of FLUO 3/AM by cytosolic esterases traps the indicator in the cell. FLUO 3 is almost nonfluorescent at resting calcium levels, but fluorescence levels increase 40-fold upon calcium binding. Unlike all other Ca²⁺ indicators, FLUO 3/AM is nonfluorescent until it is hydrolyzed by the cell. Since its excitation maximum is at 506 nm, this compound can be used in conjunction with caged compounds, which are released by UV light. Its relatively high K_d for Ca²⁺ facilitates the measurement of higher peaks of Ca²⁺ transients than is possible with FURA 2. FLUO 3 has an excitation maximum of 506 nm and an emission maximum of 526 nm in the presence of high and low calcium concentrations.

Biochem/physiol Actions

Primary Target
Ca2+ indicators

Other Notes

Caputo, C., and Bolanos, P. 1994. J. Physiol. (London)481, 119.
Schumann, M.A., et al. 1993. J. Biol. Chem. 268, 2134.
Eberhard, M., and Erne, P. 1989. Biochem. Biophys. Res. Commun.163, 309.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

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Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c