Light Sensitive Compounds for Instant Determination of Organ Function

a technology of organ function and light-sensitive compounds, which is applied in the direction of group 3/13 element organic compounds, peptides, and group 5/15 element organic compounds, can solve the problems of inability to correlate single value returned several hours after sampling with other important physiologic events, inability to obtain new or repeat data, and inability to accurately predict the effect of organ function, etc., to achieve simple, efficient and effective monitoring of organ function.

US20070140962A1Inactive Publication Date: 2007-06-21MALLINCKRODT INC
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Patent Information

Authority / Receiving Office
US · United States
Patent Type
Applications(United States)
Current Assignee / Owner
Publication Date
2007-06-21
Estimated Expiration
Not applicable · inactive patent

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Abstract

Highly hydrophilic indole and benzoindole derivatives that absorb and fluoresce in the visible region of light are disclosed. These compounds are useful for physiological and organ function monitoring. Particularly, the molecules of the invention are useful for optical diagnosis of renal and cardiac diseases and for estimation of blood volume in vivo.
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Description

RELATED APPLICATIONS

[0001] This application is a Continuation of U.S. patent application Ser. No. 10 / 751,232 filed Jan. 2, 2004, which will issue as U.S. Pat. No. 7,175,831, which is a Continuation-In-Part of U.S. patent application Ser. No. 09 / 688,942 filed Oct. 16, 2000, now U.S. Pat. No. 6,673,334, each of which are expressly incorporated by reference herein in its entirety.FIELD OF THE INVENTION

[0002] This invention relates to novel optical probes for use in physiological function monitoring, particularly indole and benzoindole compounds. BACKGROUND OF THE INVENTION

[0003] Dynamic monitoring of physiological functions of patients at the bedside is highly desirable in order to minimize the risk of acute renal failure brought about by various clinical, physiological, and pathological conditions (C. A. Rabito, L. S. T. Fang, and A. C. Waltman, Renal function in patients at risk with contrast material-induced acute renal failure: Noninvasive real-time monitoring, Radiology 1993, 1...

Examples

example 1

Synthesis of Indole Disulfonate (FIG. 1, Compound 5, Y7=SO3−: X7=H; n=1)

[0062] A mixture of 3-methyl-2-butanone (25.2 mL), and p-hydrazinobenzenesulfonic acid (15 g) in acetic acid (45 mL) was heated at 110° C. for 3 hours. After reaction, the mixture was allowed to cool to room temperature and ethyl acetate (100 mL) was added to precipitate the product, which was filtered and washed with ethyl acetate (100 mL). The intermediate compound, 2,3,3-trimethylindolenium-5-sulfonate (FIG. 1, compound 3) was obtained as a pink powder in 80% yield. A portion of compound 3 (9.2 g) in methanol (115 mL) was carefully added to a solution of KOH in isopropanol (100 mL). A yellow potassium salt of the sulfonate was obtained in 85% yield after vacuum-drying for 12 hours. A portion of the 2,3,3-trimethylindolenium-5-sulfonate potassium salt (4 g) and 1,3-propanesultone (2.1 g) was heated in dichlorobenzene (40 mL) at 110° C. for 12 hours. The mixture was allowed to cool to room temperature and the ...

example 2

Synthesis of Indole Disulfonate (FIG. 1, Compound 5 Y7=SO3−: X7=H; n=2)

[0064] This compound was prepared by the same procedure described in Example 1, except that 1,4-butanesultone was used in place of 1,3-propanesultone.

example 3

Synthesis of Benzoindole Disulfonate (FIG. 2, Compound 8, Y7, Y8=SO3−; X7=H: n=2)

[0065] This compound was prepared by the same procedure described in Example 1, except that hydrazinonaphthalenedisulfonic acid was used in place of hydrazinobenzenesulfonic acid.

[0066] Other compounds prepared by a similar method include polyhydroxyindoles such as: