Near-infrared fluorescent dyes with large stokes shifts

• US 9,250,246 B2
• Filed: 06/29/2012
• Issued: 02/02/2016
• 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): Shterengarts, Samantha
• Assistant Examiner(s): MAURO, JOHN MATTHEW
• Application Number:
  US14/129,223
• Publication Number:
  US 20140120628A1
• Time in Patent Office: 1,313 Days
• Field of Search: 549/224, 549/382, 549/213, 549/384, 436/86, 436/92
• US Class Current: 1/1
• CPC Class Codes: C07D 311/82 Xanthenes
• CPC Class Codes: C07D 493/10 Spiro-condensed systems
• CPC Class Codes: C09B 11/12 without any OH group bound to an aryl nucleus
• CPC Class Codes: C09B 11/22 containing OH groups bound to an aryl nucleus and their ethers and esters
• 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: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: G01N 21/6486 Measuring fluorescence of biological material, e.g. DNA, RNA, cells G01N21/6428 takes precedence
• CPC Class Codes: G01N 33/49 Blood chemical methods for determining blood cell populations G01N33/5094; chemical analysis of blood groups or blood types G01N33/80
• CPC Class Codes: G01N 33/493 urine
• CPC Class Codes: G01N 33/582 with fluorescent label
• CPC Class Codes: Y10T 436/141111 Diverse hetero atoms in same or different rings [e.g., alkaloids, opiates, etc.]

Abstract

Embodiments of near-infrared (NIR) dyes are disclosed, along with methods and kits for detecting analytes with the NIR dyes. The NIR dyes have a structure according to the general structure

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

Claims

1. A compound having a chemical structure selected from

2. A method for selectively detecting an analyte in a biological fluid, comprising:

combining a compound according to claim 1 with a biological fluid to form a solution;

exposing the solution to a light source; and

detecting the analyte by detecting fluorescence from the compound.

3. The method of claim 2 where detecting fluorescence from the compound comprises detecting fluorescence at a wavelength corresponding to an emission spectrum maximum of the compound, the method further comprising quantitating the analyte by measuring an amount of fluorescence from the compound at a wavelength corresponding to an emission spectrum maximum of the compound.

4. The method of claim 2 where the biological fluid comprises blood or urine.

5. A kit for detecting an analyte, comprising at least one compound according to claim 1, wherein the compound when combined with a sample comprising the analyte will undergo a change in its absorbance spectrum and/or emission spectrum compared to the compound in a sample that does not comprise the analyte.

6. The kit of claim 5, further comprising at least one buffer solution in which the compound when combined with a sample comprising the analyte will undergo a change in its absorbance spectrum and/or emission spectrum compared to the compound combined with the buffer solution and a sample that does not comprise the analyte.