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Increasing the Luminescence of Lanthanide(III) Macrocyclic Complexes, Continuation

Disclosed are a spectrofluorimetrically detectable luminescent composition and processes for enhancing the luminescence of one or more lanthanide-containing macrocycles. The luminescent composition comprises a micelle-producing amount of at least one surfactant, at least one energy transfer acceptor lanthanide element macrocycle compound having an emission spectrum peak in the range from 500 to 950 nanometers, and a luminescence-enhancing amount of at least one energy transfer donor compound of yttrium or a 3-valent lanthanide element having atomic number 59-71, provided that the lanthanide element of said macrocycle compound and the lanthanide element of said energy transfer donor compound are not identical. The addition of gadolinium(III) in the presence of other solutes to both the prototype and the di-functionalized europium, samarium, and terbium macrocyclic complexes, which were taught in our U.S. Pat. Nos. 5,373,093 and 5,696,240, enhances their luminescence. Similar enhancements of luminescence also results for the mono-functionalized europium, samarium, and terbium macrocyclic complexes, which were taught in our U.S. Pat. No. 5,696,240. The enhanced luminescence afforded by the composition enables the detection and/or quantitation of many analytes in low concentrations without the use of expensive, complicated time-gated detection systems.

A Reagent System and Method for Increasing the Luminescence of Lanthanide(III) Macrocyclic Complexes, R. C. Leif and L. M. Vallarino, 6,750,005 (2004).

Increasing the Luminescense of Lanthanide(III) Macrocyclic Complexes

Disclosed are a spectrofluorimetrically detectable luminescent composition and processes for enhancing the luminescence of one or more lanthanide-containing macrocycles. The luminescent composition comprises a micelle-producing amount of at least one surfactant, at least one energy transfer acceptor lanthanide element macrocycle compound having an emission spectrum peak in the range from 500 to 950 nanometers, and a luminescence-enhancing amount of at least one energy transfer donor compound of yttrium or a 3-valent lanthanide element having atomic number 59-71, provided that the lanthanide element of said macrocycle compound and the lanthanide element of said energy transfer donor compound are not identical. The addition of gadolinium(III) in the presence of other solutes to both the prototype and the di-functionalized europium, samarium, and terbium macrocyclic complexes, which were taught in our U.S. patents #5,373,093 and #5,696,240, enhances their luminescence. Similar enhancements of luminescence also results for the mono-functionalized europium, samarium, and terbium macrocyclic complexes, which were taught in our U.S. patent #5,696,240. The enhanced luminescence afforded by the composition enables the detection and/or quantitation of many analytes in low concentrations without the use of expensive, complicated time-gated detection systems.

A Reagent System and Method for Increasing the Luminescence of Lanthanide(III) Macrocyclic Complexes, R. C. Leif and L. M. Vallarino, 6,340,744 (2002).

Macrocycle Complexes of Yttrium, Continuation in Part

Symmetrically di-functionalized water soluble macrocyclic complexes of lanthanide, actinide and yttrium ions were obtained by metal templated, Schiff-base, cyclic condensation of: (1) a functionalized 1,2-diaminoethane and a dicarbonyl compound selected from the group consisting of 2,6-dicarbonylpyridine, 2,6-diformylpyridine, 2,5-dicarbonylfuran, 2,5-diformylfuran, 2,5-dicarbonyl-thiophene and 2,5-diformylthiophene; or (2) 1,2-diaminoethane and a ring-substituted heterocyclic dicarbonyl compound selected from a group consisting of substituted 2,6-dicarbonylpyridine, substituted 2,6-diformylpyridine, substituted 2,5-dicarbonylfuran, substituted 2,5-diformylfuran; substituted 2,5-dicarbonyl thiophene, and substituted 2,5-diformylthiophene. Asymmetrically functionalized water soluble macrocyclic complexes of the lanthanide, actinide and yttrium ions were obtained by metal templated, Schiff-base, cyclic condensation of appropriately substituted diamine and dicarbonyl precursors, with such precursors contributing two heteroaromatic moieties (pyridine, furan, thiophene, or a combination thereof) to the resulting macrocyclic structure. The coordination complexes thus formed are kinetically stable in dilute aqueous solution. They are further reacted, or coupled, through a substituent on the 1,2-diaminoethane or on the pyridine, furan, or thiophene moieties, to one of the following: proteinaceous materials, polysaccharides, polynucleotides, other biologically compatible macromolecules or bridging molecules which, can be further reacted or coupled to the above mentioned substrates. These macrocyclic complexes are suitable in the preparation of reporter molecules and for magnetic resonance, radiation imaging and radiation therapy.

 

Macrocycle complexes of Yttrium, the Lanthanides and the Actinides having Peripheral Coupling Functionalities Continuation in part, L. M. Vallarino and R. C. Leif, 5,696,240 (1997).

Macrocycle Complexes of Yttrium

Functionalized water soluble macrocyclic complexes of lanthanide, actinide and yttrium ions were obtained by metal templated, Schiff-base, cyclic condensation of: (1) a functionalized 1,2-diaminoethane and a dicarbonyl compound selected from the group consisting of 2,6-dicarbonylpyridine, 2,6-diformylpyridine, 2,5-dicarbonylfuran, 2,5-diformylfuran, 2,5-dicarbonylthiophene and 2,5-diformylthiophene; or (2) 1,2-diaminoethane and a ring-substituted heterocyclic dicarbonyl compound selected from a group consisting of substituted 2,6-dicarbonylpyridine, substituted 2,6-diformylpyridine, substituted 2,5-dicarbonylfuran, substituted 2,5-diformylfuran; substituted 2,5-dicarbonyl thiophene, and substituted 2,5-diformylthiophene. Coordination complexes thus formed are kinetically stable in dilute aqueous solution. They are further reacted, or coupled, through a substituent on the 1,2-diaminoethane or on the pyridine, furan, or thiophene moieties, to one of the following: proteinaceous materials, polysaccharides, other biologically compatible macromolecules or bridging molecules which, can be further reacted or coupled to the above mentioned substrates. These macrocyclic complexes are suitable in the preparation of reporter molecules and for magnetic resonance, radiation imaging and radiation therapy.

Macrocycle complexes of Yttrium, the Lanthanides and the Actinides having Peripheral Coupling Functionalities,L. M. Vallarino and R. C. Leif, 5,373,093, (1994).

Pending

Conjugated Polymer Tag Complexes

Processes are described for: (1) the sequential solid phase synthesis of polymers with at least one tag, which can be a light emitting and/or absorbing molecular species (optical-label), a paramagnetic or radioactive label, or a tag that permits the physical separation of particles including cells. When multiple optical-labels are suitably arranged in three-dimensional space, the energy transfer from one molecular species to another can be maximized and the radiationless loss between members of the same molecular species can be minimized; (2) the coupling of these polymers to biologically active and/or biologically compatible molecules through peripheral pendant substituents having at least one reactive site; and (3) the specific cleavage of the coupled polymer from a solid phase support. The tagged-peptide or polymers produced by these processes and their conjugates with an analyte-binding species, such as a monoclonal antibody or a polynucleotide probe are described. When functionalized europium macrocyclic complexes, as taught in our U.S. patents 5,373,093 and 5,696,240, are bound to polylysine and other peptides, the emitted light increases linearly with the amount of bound macrocyclic complex. Similar linearity will also result for multiple luminescent macrocyclic complexes of other lanthanide ions, such as samarium, terbium, and dysprosium, when they are bound to a polymer or molecule.

Conjugated Polymer Tag Complexes,R. C. Leif. and L. M. Vallarino, PCT WO 01/27625 A1, published (2001).

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