Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1989-08-09
1992-07-28
Rizzo, Nicholas S.
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
540469, C07D27308
Patent
active
051342324
ABSTRACT:
The invention discloses fluorescent chelator compounds that are especially useful to monitor and measure cytosolic concentrations of alkali metal cations such as Na.sup.+, K.sup.+, and Li.sup.+. The new compounds are comprised of: (1) crown ethers (that may or may not have substituent groups attached to the core carbons, but will always contain at least one core nitrogen) that are linked via the core nitrogen(s) to at least one (2) fluorophore that contains an additional heteroaromatic liganding center. In the currently preferred dye, SBFI, the core compound is crown ether 1,7-diaza-4,10,13-trioxacyclopentadecane and the heteroaromatic fluorophores are benzofurans that are linked to isophthalate groups. Selectivities for Na.sup.+ over K.sup.+ of about 20 are observed, resulting in effective dissociation constants for Na.sup.+ of about 20 mM against a background of 120 mM K.sup.+. Increasing [Na.sup.+ ] increases the ratio of excitation efficiency at 330-345 nm to that at 370-390 nm with emission collected at 450-550 nm, so that ratio fluorometry and imaging work at the same wavelengths as used with the well-known Ca.sup.2+ indicator fura-2. If the macrocyclic ring is increased in size to a 1,10-diaza-4,7,13,16-tetraoxacyclooctadecane, the chelators become selective for K.sup.+ over Na.sup.+. If the ring is decreased in size, for example to a 1,7-diaza-4,10-dioxacyclododecane, the chelators become selective for Li.sup.+ over Na.sup.+.
REFERENCES:
patent: 4597903 (1986-07-01), Gokel et al.
patent: 4927923 (1990-05-01), Mathis et al.
Minta Akwasi
Tsien Roger Y.
Rizzo Nicholas S.
The Regents of the University of California
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