Indo-1

Indo-1 is a popular calcium indicator similar to Fura-2. In contrast to Fura-2, Indo-1 has a dual emissions peak. The main emission peak in calcium-free solution is 475 nm while in the presence of calcium the emission is shifted to 400 nm. It is widely used in flow cytometry. The penta potassium salt is commercially available and preferred to the free acid because of its higher solubility in water. While Indo-1 is not cell permeable the penta acetoxymethyl ester Indo-1 AM enters the cell where it is cleaved by intracellular esterases to Indo-1. The synthesis and properties of Indo-1 were presented in 1985 by the group of Roger Y Tsien.[1]

Indo-1
Names
IUPAC name
2-[4-(bis(carboxymethyl)amino)-3-[2-[2-(bis(carboxymethyl)amino)- 5-methylphenoxy]ethoxy]phenyl]-1H-indole-6-carboxylic acid
Other names
Indo-1
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C32H31N3O12/c1-18-2-6-24(34(14-28(36)37)15-29(38)39)26(10-18)46-8-9-47-27-13-20(5-7-25(27)35(16-30(40)41)17-31(42)43)22-11-19-3-4-21(32(44)45)12-23(19)33-22/h2-7,10-13,33H,8-9,14-17H2,1H3,(H,36,37)(H,38,39)(H,40,41)(H,42,43)(H,44,45) checkY
    Key: AMHAQOBUZCQMHN-UHFFFAOYSA-N checkY
  • InChI=1/C32H31N3O12/c1-18-2-6-24(34(14-28(36)37)15-29(38)39)26(10-18)46-8-9-47-27-13-20(5-7-25(27)35(16-30(40)41)17-31(42)43)22-11-19-3-4-21(32(44)45)12-23(19)33-22/h2-7,10-13,33H,8-9,14-17H2,1H3,(H,36,37)(H,38,39)(H,40,41)(H,42,43)(H,44,45)
    Key: AMHAQOBUZCQMHN-UHFFFAOYAU
  • O=C(O)CN(c4ccc(cc4OCCOc3c(N(CC(=O)O)CC(=O)O)ccc(c2cc1ccc(cc1[nH]2)C(=O)O)c3)C)CC(=O)O
Properties
C32H31N3O12
Molar mass 649.60 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Grynkiewicz G, Poenie M, Tsien RY (1985). "A new generation of Ca2+ indicators with greatly improved fluorescence properties". J. Biol. Chem. 260 (6): 3440–50. doi:10.1016/S0021-9258(19)83641-4. PMID 3838314.


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