Lipid-based metal sensor

• US 5,616,790 A
• Filed: 11/18/1994
• Issued: 04/01/1997
• Est. Priority Date: 11/18/1994
• Status: Expired due to Fees

• Current Assignee: California Institute of Technology
• Original Assignee: California Institute of Technology
• Inventors: Pack, Daniel, Shnek, Deborah, Arnold, Frances H., Sasaki, Darryl Y.
• Primary Examiner(s): Geist, Gary
• Assistant Examiner(s): Frazier, Barbara S.
• Application Number:
  US08/342,369
• Time in Patent Office: 865 Days
• Field of Search: 362/444, 540/474, 422/82.08
• US Class Current: 562/444
• CPC Class Codes: C09B 57/10 Metal complexes of organic compounds not being dyes in uncomplexed form
• CPC Class Codes: G01N 31/22 using chemical indicators G01N31/02 takes precedence
• CPC Class Codes: G01N 31/221 for investigating pH value
• CPC Class Codes: G01N 33/533 with fluorescent label

Abstract

An fluorescent metal-chelating amphiphile having the structure: ##STR1## wherein A is a hydrophobic fluorophore, X and Y are aliphatic hydrocarbons having from 9 to 25 carbon atoms, B is a hydrophilic spacer, C is a metal chelator, and L is either an ether or ester linkage. The fluorescent metal-chelating amphiphile is combined with a matrix lipid to form lipid-based sensors which provide fluorometric detection of metal ions in liquids.

Claims

1. A fluorescent metal-chelating amphiphile for use in a sensor for detecting the presence of a metal ion in a liquid, said fluorescent metal-chelating amphiphile having the structure:

##STR4## wherein A is a hydrophobic fluorophore, X and Y are aliphatic hydrocarbons having from 9 to 25 carbon atoms, B is a hydrophilic spacer, C is a metal chelator, and L is either an ether or ester linkage.

2. A fluorescent metal-chelating amphiphile according to claim 1 wherein A is a fluorophore selected from the group consisting of pyrene, anthracene, naphthalene, and phenanthrene and their derivatives.

3. A fluorescent metal-chelating amphiphile according to claim 1 wherein C is a metal chelator selected from the group consisting of iminodiacetic acid, penicillamine, dimercaptosuccinic acid, tartrate, thiomalic acid, nitrolotriacetatic acid (NTA), ethylenediaminetetraacetic acid (EDTA), ethylenebis(oxyethylenenitrilo)tetraacetic acid (EGTA), 3,6-dioxaoctanedithioamide, 3,6-dioxaoctanediamide, dithiooxamide, 2,2'"'"'-thiobis(ethyl acetoacetate).

4. A fluorescent metal-chelating amphiphile according to claim 3 wherein C is iminodiacetic acid.

5. A fluorescent metal-chelating amphiphile according to claim 3 wherein A is a fluorophore selected from the group consisting of pyrene, naphthalene, anthracene and phenanthrene.

6. A fluorescent metal-chelating amphiphile according to claim 2 wherein C is iminodiacetic acid.

7. A fluorescent metal-chelating amphiphile according to claim 2 wherein said fluorophore is pyrene or phenanthrene.

8. A fluorescent metal-chelating amphiphile according to claim 4 wherein C is iminodiacetic acid.

9. A fluorescent metal-chelating amphiphile according to claim 1 wherein C is a metal chelator selected from the group consisting of salicyladoximine, 8-hydroxyquinoline, cupferron and 2,2'"'"'-dipyridyl.

10. A fluorescent metal-chelating amphiphile according to claim 1 wherein C is a metal chelator selected from the group consisting of cyclam and crown ethers.