Analyte detection using near-infrared fluorophores

• US 10,197,574 B2
• Filed: 01/28/2016
• Issued: 02/05/2019
• Est. Priority Date: 06/29/2011
• Status: Active Grant

• Current Assignee: Portland State University (Oregon University System)
• Original Assignee: Portland State University (Oregon University System)
• Inventors: Strongin, Robert Michael, Sibrian-Vazquez, Martha, Escobedo-Cordova, Jorge Omar, Lowry, Mark Allen
• Primary Examiner(s): Morris, Patricia L
• Application Number:
  US15/009,213
• Publication Number:
  US 20160223558A1
• Time in Patent Office: 1,104 Days
• Field of Search: 546258
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C09B 11/24 Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 9/02 Organic tenebrescent materials
• CPC Class Codes: G01N 2800/28 Neurological disorders
• CPC Class Codes: G01N 33/52 Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements immunological elements G01N33/54386; involving labelled immunochemicals G01N33/58; for haemoglobin or occult blood G01N33/72
• CPC Class Codes: G01N 33/582 with fluorescent label
• CPC Class Codes: G01N 33/6815 containing sulfur, e.g. cysteine, cystine, methionine, homocysteine
• CPC Class Codes: Y10T 436/143333 Saccharide [e.g., DNA, etc.]

Abstract

Embodiments of compounds for selectively detecting an analyte are disclosed, along with methods and kits for detecting analytes with the compounds. The compounds are bridged viologen conjugates including at least one fluorophore according to the general structure

At least one of R¹/R², R²/R³, R³/R⁴, R⁵/R⁶, R⁶/R⁷, and/or R⁷/R⁸ together form a substituted or unsubstituted cycloalkyl or aryl.

Claims

1. A compound according to Formula III

2. The compound of claim 1 where R¹³ is the linker.

3. The compound of claim 1 where R¹³ is —

COO— and

forms a lactone ring, and at least one of R¹, R², or R⁵-R¹² or -R¹⁵-R¹⁸ is the linker.

4. The compound of claim 1 where the fluorophore has a structure according to:

(a) formula (iii) R¹⁸ is halogen, hydroxyl, thiol, amino, alkyl amino, or alkoxy;

or

(b) formula (iii) where R⁶ and R¹⁶ are —

NHR^c.

5. A method for detecting an analyte, comprising:

forming a solution by combining a sample comprising an analyte with a compound according to claim 1;

allowing a reaction between the analyte and the compound in the solution to proceed for an effective period of time to a produce a detectable change in the solution'"'"'s absorbance spectrum, emission spectrum, or both, where the change indicates that the analyte is present; and

detecting the change.

6. The method of claim 5 where detecting the change comprises:

exposing the solution to a light source; and

detecting the analyte by detecting fluorescence from the compound at a wavelength corresponding to an emission spectrum maximum of the compound after the reaction has proceeded for the effective period of time.

7. The method of claim 5 where the analyte comprises cysteine, homocysteine, glutathione, succinyl-5-amino-4-imidazolecarboxamide riboside, succinyladenosine, or a combination of succinyl-5-amino-4-imidazolecarboxamide riboside and succinyladenosine.

8. The method of claim 7 where the analyte is succinyl-5-amino-4-imidazolecarboxamide riboside, succinyladenosine, or a combination thereof, and the compound comprises at least one fluorophore according to:

(a) formula (iii);