Organic compounds -- part of the class 532-570 series – Organic compounds – Rare earth containing
Patent
1994-07-26
1996-11-05
Kight, John
Organic compounds -- part of the class 532-570 series
Organic compounds
Rare earth containing
534 16, 540465, 540467, 540470, 540474, 540480, 540481, 546 2, 546 5, 546256, 5462704, 5462714, 5462741, 5462754, 5462764, 5462724, 5462694, 5462834, 546 6, 546332, 546313, 546323, C07F 500, C07J 2100, C07D40150, C07D41300
Patent
active
055718973
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/FI91/00373 filed Dec. 5, 1991, WO93/11433.
FIELD OF THE INVENTION
The invention pertains no new luminescent lanthanide chelates comprising three unsaturated heterocyclic rings covalently coupled to each other and additionally comprising two chelating groups. This structure of three heterocyclic rings is formed of one or two 2,6-pyridylene moieties and five-membered unsaturated heterocyclic rings.
The new chelates of our invention find applications in those areas that are classical for lanthanide chelates and known in the art. Moreover, these compounds are useful as probes in time-resolved fluorescence microscopy, cytometry, multilabelling techniques and process controls in industry.
DESCRIPTION OF THE PRIOR ART
In immunoassays and DNA hybridization assays time-resolved luminescence spectroscopy using lanthanide chelates is well known ( e g. I. A. Hemmil a, "Applications of Fluorescence in Immunoassays" in J. D. Winefordner and I. M. Kolthoff, Eds., Chemical Analysis; Vol 117, John Wiley & Sons, Inc., USA, 1991 and the references therein). Stable luminescent lanthanide chelates also have other applications, e.g. fluorescence microscopy and cytometry. Because of their paramagnetic properties, these lanthanide chelates are useful as sensitive probes in magnetic resonance imaging (MRI). The radioactive isotopes of metals such as indium and stable chelating ligands on the macromolecules offer possibilities to use the ligands of this invention in the treatment of diseases such as cancer.
Luminescent lanthanide chelates have previously been proposed [macropolycycles: French Patent No. 2,570,703 (1986) and Eur. Patent Appl. 321,353 (1988); phenols: U.S. Pat. No. 4,670,572 (1987); coumarines: U.S. Pat. No. 4,801,722 (1989) and U.S. Pat. No. 4,794,191 (1988); polypyridines: U.S. Pat. No. 4,837,169 (1989), U.S. Pat. No. 4,859,777 (1989), Int. Pat. Appl. PCT/SE89/00073 (1989) and Int. Pat. Appl. PCT/SE89/00379 (1989); aryl pyridines: U.S. Pat. 4,761,481 (1988) and Int. Pat. Appl. PCT/WO89/04826; ethynyl pyridines: U.S. Pat. No. 4,920,195 (1990); phenanthrolines: U.S. Pat. No. 4,772,563 (1988); salicylates: M. P. Bailey, B. F. Rocks and C. Riley, Analyst, 109, 1449 (1984)].
Stable luminescent lanthanide chelates, whose energy absorbing group comprises either one 2,6-pyridylene and two five-membered unsaturated heterocyclic ring moieties, or two 2,6-pyridylene moieties and one five-membered unsaturated heterocyclic ring moiety coupled to each other with a covalent bond between the carbon atoms, are non known. Some basic structures comprising three heterocyclic rings covalently coupled to each other (including one or two pyridine rings) have been synthesized (see e.g. V. Nair and K. H. Kim, J. Heterocyclic Chem. 13 (1976), 873; S. Kubota and H. Ohtsuka, Tokushima Daigcaku Yakugaku Kenkyu Nempo 9 (1963) 15, CA58:2449a; J. F. Geldhard and F. Lions, J. Org. Chem. 30 (1965) 318; R. Menasse, G. Klein an H. Erlenmeyer, Helv. Chim. Acta, 38 (1955) 1289; H. A. Goodwin, Aust. J. Chem 17 (1964) 1366; R. J. Clark and J. Walker, J. Chem. Soc.C 6 (1966) 1354; S. Gronowitz and D. Peters, Heterocycles 30(1) (1990) 645 and A. T. Parker, P. Singh and V. Vignevich, Aust. J. Chem. 44 (1991) 1041). As such, these compounds are not stable enough for use with lanthanide ions in aqueous solution. A lanthanide chelate, containing one 2,6-pyridylene and two 1,3-pyrazolylene groups, and having a covalent bond between the carbon and nitrogen atoms, has been synthesized (M. Alanso, J. de Mendoza, M. Remui nan, H. Roman and J. C. Rodriguez-Ubis, 2nd Conference on Methods and Applications of Fluorescence Spectroscopy, Graz, Austria, 14-17.10.1991, P1/25). The luminescence properties of this chelate have not been published. The chelate has no group for coupling to biologically active material and it cannot be used as such for applications mentioned in this invention.
THE INVENTION
The compounds of this invention are lanthanide chelates comprising three heterocyclic rings covalently coupled to each other (eithe
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Mukkala Veli-Matti
Takalo Harri
Chapman Lara E.
Kight John
Kubovcik Ronald J.
Wallac Oy
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