(acetyloxy)methyl 2-({2-[(acetyloxy)methoxy]-2-oxoethyl}[3',6'-bis(acetyloxy)-5'-{[bis({2-[(acetyloxy)methoxy]-2-oxoethyl})amino]methyl}-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-4'-ylmethyl]amino)acetate

• ChemBase ID: 155831
• Molecular Formular: C46H46N2O23
• Molecular Mass: 994.85704
• Monoisotopic Mass: 994.24913574
• SMILES: CC(=O)OCOC(=O)CN(Cc1c(ccc2c1Oc1c(ccc(c1CN(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C)OC(=O)C)C12c2ccccc2C(=O)O1)OC(=O)C)CC(=O)OCOC(=O)C
• Canonical SMILES: O=C(CN(Cc1c(ccc2c1Oc1c(CN(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C)c(ccc1C12OC(=O)c2c1cccc2)OC(=O)C)OC(=O)C)CC(=O)OCOC(=O)C)OCOC(=O)C
• 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
• InChIKey: XKFSBWQWNMZWFA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (acetyloxy)methyl 2-({2-[(acetyloxy)methoxy]-2-oxoethyl}[3',6'-bis(acetyloxy)-5'-{[bis({2-[(acetyloxy)methoxy]-2-oxoethyl})amino]methyl}-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-4'-ylmethyl]amino)acetate
• IUPAC Traditional name: (acetyloxy)methyl 2-({2-[(acetyloxy)methoxy]-2-oxoethyl}[3',6'-bis(acetyloxy)-5'-{[bis({2-[(acetyloxy)methoxy]-2-oxoethyl})amino]methyl}-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-ylmethyl]amino)acetate
• Synonyms: Calcein O,O′-diacetate tetrakis(acetoxymethyl) ester; Calcein acetoxymethyl ester; Calcein-AM; N,N'-[[3',6'-Bis(acetyloxy)-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-2',7'-diyl]bis(methylene)]bis[N-[2-[(acetyloxy)methoxy]-2-oxoethyl]glycine 1,1'-Bis[(acetyloxy)methyl] Ester; NSC 689290; Calcein AM; Calcein AM solution

Database IDs

• CAS Number: 148504-34-1
• EC Number: 200-664-3
• MDL Number: MFCD05861516
• PubChem SID: 24850694; 24892405; 162249969
• PubChem CID: 4126474

CALCULATED PROPERTIES

• H Acceptors: 13
• H Donor: 0
• LogD (pH = 5.5): 1.5229716
• LogD (pH = 7.4): 1.5247728
• Log P: 1.5247958
• Molar Refractivity: 231.0365 cm^3
• Polarizability: 92.298676 Å^3
• Polar Surface Area: 305.01 Å^2
• Rotatable Bonds: 32
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: liquid
• Flash Point: 185 °F; 85 °C
• Fluorescence: λex 496 nm; λem 516 nm in 0.1 M Tris pH 8.0, esterase; Ca2+

Safety Information

• German water hazard class: 2; 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US); Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC); ≥96.0% (HPLC)
• Concentration: ≥4 mM in DMSO
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C46H46N2O23

DETAILS

Sigma Aldrich - 17783

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
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.

Sigma Aldrich - C1359

Biochem/physiol Actions
Fluorescent cell permeable derivative of calcein.
Physical form
Solution in 0.4% Calcein AM and 99.6% DMSO.

Toronto Research Chemicals - C125400

Calcein-AM is a hydrophobic non-fluorescent probe that can permeate the plasma membrane and can be hydrolyzed to Calcein (sc-202090), which is an extremely fluorescent and negatively charged molecule. Calcein-AM can be used to stain living cells and in cy

REFERENCES

• Feller, N., et al.: Br. J. Cancer, 72, 543 (1995)
• Dhar, S., et al.: Eur. J. Pharmacol., 346, 315 (1995)
• Essodaigui, M., et al.: Biochemistry, 37, 2243 (1995)
• Lemasters, J.J., et al.: Biochim. Biophys. Acta., 1366,177 (1995)