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| Method of cleaning membrane filter |
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| Electrochemical power generation |
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Fluorophores for encapsulation into liposomes
| Details |
Inventors: Fiechtner, Michael D.; Bieniarz, Christopher; Shipchandler, Mohamed; Adamczyk, Maciej;
Assignee: Abbott Laboratories (Abbott Park, IL)
Primary Examiner: Griffin; Ronald W.
Assistant Examiner:
Attorney, Agent or Firm: Hastreiter; Roberta L.
The present invention provides novel fluorescein derivative compounds having fluorescence spectrum and quantum yield characteristics similar to those of fluorescein. The compounds are readily synthesized and purified and are readily soluble in water at self-quenching concentrations. Significantly, due to the presence of polar polyhydroxy group substituents and the absence of metal-chelating groups, these fluorescein derivatives are susceptible to minimal leakage across liposome membranes and have fluorescence characteristics minimally sensitive to the presence of metal ions. Compounds of the invention are thus exceptionally suitable for use in the development of highly storage stable liposome preparations to be employed in immunolytic assays involving human body fluid samples. |
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DETAILED DESCRIPTION The present invention relates to the discovery and synthesis of novel fluorophores which can be encapsulated and maintained within synthetic liposomes without significant leakage over longer periods of time.
When encapsulated at high concentrations, on the order of 50-200 mM, depending upon the signal strength required, the fluorophores are self-quenched and, upon liposome lysis, fluorescence is re-established and can be readily measured.
The following examples illustrate practice of the invention.
Example 1 relates to the synthesis of the fluorophores.
Example 2 relates to the preparation of liposomes and the encapsulation of the fluorophores and Example 3 relates to leakage studies.
The examples which follow are for illustrative purposes and are not intended to limit the scope of the invention.
EXAMPLE 1 Synthesis of Fluorophores The fluorophores are generally obtained in an isomeric mixture of both the 5- and the 6-isomeric forms owing to the starting materials used to prepare the fluorophores.
The N-hydroxysuccinimide ester of 5(6)-carboxyfluorescein, is used as a starting material for 5(6)-carboxyfluorescein-N-methylglucamide; 5(6)-carboxyfluorescein-tris(methylol)methylamide; 5-carboxyfluorescein-diethanolamide; 5(6)-carboxyfluorescein-N-(.
beta.
-hydroxyethyl)-maltosamide; 5(6)-carboxyfluorescein-galactosamide; and 5(6)-carboxyfluorescein-pyridoxamide.
5(6)-carboxyfluorescein-N-methylglucamide is used as the starting material for 5(6)-carboxyfluorescein-tris(methylol)methylamide-4',5'bis(methylene diethanolamine); 5(6)-carboxyfluorescein-N-methylglucamide-4',5'-bis(methylenediethanolamin e); 5(6)-carboxyfluorescein-N-methylglucamide-4',5'-bis(N-methylglucaminomethy l); 5(6)-carboxyfluorescein-N-methylglucamide-4',5'-bis(methyleneiminodiacetic acid); and 5(6)-carboxyfluorescein-4',5'-bis(methylene-sarcosine).
5(6)-carboxyfluorescein (Eastman Organic Chemicals; Rochester, N.
Y.
) is used as the starting material for 5(6)-carboxyfluorescein-4',5'bis(methyleneiminodiacetic acid)
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