(acetyloxy)methyl 2-({2-[(acetyloxy)methoxy]-2-oxoethyl}(2-{2-[5-(6-{[(acetyloxy)methoxy]carbonyl}-1H-indol-2-yl)-2-[bis({2-[(acetyloxy)methoxy]-2-oxoethyl})amino]phenoxy]ethoxy}-4-methylphenyl)amino)acetate

• ChemBase ID: 103584
• Molecular Formular: C47H51N3O22
• Molecular Mass: 1009.91474
• Monoisotopic Mass: 1009.29642029
• SMILES: CC(=O)OCOC(=O)CN(CC(=O)OCOC(=O)C)c1ccc(C)cc1OCCOc1c(ccc(c1)c1cc2c([nH]1)cc(cc2)C(=O)OCOC(=O)C)N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C
• Canonical SMILES: CC(=O)OCOC(=O)CN(c1ccc(cc1OCCOc1cc(C)ccc1N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C)c1[nH]c2c(c1)ccc(c2)C(=O)OCOC(=O)C)CC(=O)OCOC(=O)C
• InChI: InChI=1S/C47H51N3O22/c1-28-7-11-39(49(19-43(56)68-23-63-29(2)51)20-44(57)69-24-64-30(3)52)41(15-28)61-13-14-62-42-18-35(37-16-34-8-9-36(17-38(34)48-37)47(60)72-27-67-33(6)55)10-12-40(42)50(21-45(58)70-25-65-31(4)53)22-46(59)71-26-66-32(5)54/h7-12,15-18,48H,13-14,19-27H2,1-6H3
• InChIKey: CAWBRCOBJNWRLK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (acetyloxy)methyl 2-({2-[(acetyloxy)methoxy]-2-oxoethyl}(2-{2-[5-(6-{[(acetyloxy)methoxy]carbonyl}-1H-indol-2-yl)-2-[bis({2-[(acetyloxy)methoxy]-2-oxoethyl})amino]phenoxy]ethoxy}-4-methylphenyl)amino)acetate
• IUPAC Traditional name: (acetyloxy)methyl 2-({2-[(acetyloxy)methoxy]-2-oxoethyl}(2-{2-[5-(6-{[(acetyloxy)methoxy]carbonyl}-1H-indol-2-yl)-2-[bis({2-[(acetyloxy)methoxy]-2-oxoethyl})amino]phenoxy]ethoxy}-4-methylphenyl)amino)acetate
• Synonyms: Indo 1-AM; 4-(6-Carboxy-2-indolyl)-4′-methyl-2,2′-(ethylenedioxy)dianiline-N,N,N′,N′-tetraacetic acid tetrakis(acetoxymethyl) ester; Indo 1-AM analog; Mag-Indo 1-AM; 4-(6-Carboxy-2-indolyl)-4'-methyl-2,2'-(ethylenedioxy)dianiline-N,N,N',N'-tetraacetic acid tetrakis(acetoxymethyl) ester; INDO 1-AM

Database IDs

• CAS Number: 130926-94-2; 112926-02-0; 0
• MDL Number: MFCD00036955
• PubChem SID: 24874759; 24896026; 24850468; 162103013
• PubChem CID: 123918

CALCULATED PROPERTIES

• Acid pKa: 13.303109
• H Acceptors: 14
• H Donor: 1
• LogD (pH = 5.5): 3.65973
• LogD (pH = 7.4): 3.6597295
• Log P: 3.65973
• Molar Refractivity: 239.7786 cm^3
• Polarizability: 97.323654 Å^3
• Polar Surface Area: 303.73 Å^2
• Rotatable Bonds: 37
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: acetonitrile: soluble10 mg/mL, clear; DMSO: soluble
• Fluorescence: λex 328 nm; λem 416 nm in 0.1 M Tris pH 8.0, esterase; Mg2+; λex 330 nm; λem 398 nm in 0.1 M Tris pH 8.0, 10 mM Ca2+ (after cleavage by esterase); λex 330 nm; λem 450 nm (with Calcium); λex 356 nm; λem 478 nm in methanol

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ~95% (HPLC); ≥95% (HPLC)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C33H34N2O17; C47H51N3O22

DETAILS

MP Biomedicals - 02152288

The acetoxymethyl ester of INDO 1. Able to permeate cell membranes, is then rapidly hydrolyzed by cytoplasmic esterases, releasing INDO 1 inside the cell, where it remains trapped.

Sigma Aldrich - 17375

Application
Cell permeable fluorescent derivative of indicator for Mg2+

Sigma Aldrich - 57182

Other Notes
Cell-permeant derivative of Indo 1; Quant. assessment of intracellular free calcium concns. using ratiometric fluorescence technique1

Sigma Aldrich - I3261

Application
Cell permeable fluorescent probe for Ca2+; lower affinity than FURA 2; gives a large shift in fluorescent emission from 482 nm to 398 nm upon Ca2+ binding.