IP Library Granted Patent US 9,896,711
Granted Patent B2
US 9,896,711 · App. 15/226,096 · Granted Feb 20, 2018

Fluorogenic or fluorophoric compounds and uses thereof

Inventors: Stephen B. Roscoe (Woodbury, MN); Shih-Hung Chou (Maplewood, MN); Stephanie J. Moeller (Stillwater, MN); Jesse D. Miller (Hudson, WI); Kurt J. Halverson (Lake Elmo, MN); Jason W. Bjork (Newport, MN)
Assignee: 3M Innovative Properties Company
C12Q1/04C07D311/16C07D405/04C07D409/04C07H17/075C09B57/02C12Q1/045G01N33/525G01N33/582
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Quick Facts
Patent No.
US 9,896,711
App. No.
15/226,096
Granted
Feb 20, 2018
Kind
B2
Abstract

Compounds are provided that are either fluorogenic or fluorophoric. Compositions and articles that include the compounds are also provided. Additionally, methods of detecting a microorganism using the compounds are provided. The compounds are fluorinated and can be used advantageously under acidic conditions.

Claims (14)

1. A method of detecting a microorganism, the method comprising:

providing a fluorogenic compound of Formula (Ia)

wherein

R 1 is —(CO)—OR 3 , —(CO)—NR 4 R 5 , heterocyclic group, aryl, aralkyl, or cyano;

R 2a is an enzyme-labile group;

R 3 is alkyl, alkenyl, aryl, or aralkyl;

R 4 and R 5 are each independently hydrogen, alkyl, aryl, or aralkyl; and

either (a) X1 is hydrogen and X2 is fluoro or (b) X1 is fluoro and X2 is hydrogen; and

incubating a test sample with the fluorogenic compound of Formula (Ia), wherein the test sample contains an enzyme that cleaves reacts with group R 2a resulting in the formation of a fluorophoric compound of Formula (Ib); and

exciting the fluorophoric compound of Formula (Ib) with a first wavelength of light and detecting light emitted at a second wavelength of light that is longer than first wavelength of light.

2. The method of claim 1 , wherein the first wavelength of light and the second wavelength of light are in the ultraviolet, visible, or infrared region.

3. The method of claim 1 , wherein the step of incubating the test sample with the fluorogenic compound comprises adding the test sample in a liquid form to a dehydrated layer containing the fluorogenic compound of Formula (Ia) and a growth medium.

4. The method of claim 1 , wherein the method further comprises sequestering the compound of Formula (Ib) on polymeric particles.

5. The method of claim 1 , wherein the polymeric particles have an average particle diameter in a range of 0.01 micrometers to 1 micrometer.

Assignments (3)
SECURITY INTEREST Recorded Sep 2, 2022
From: NEOGEN CORPORATION; NEOGEN FOOD SAFETY US HOLDCO CORPORATION
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 061372/0264 →
PATENT ASSIGNMENT AGREEMENT Recorded Sep 1, 2022
From: 3M INNOVATIVE PROPERTIES COMPANY
To: GARDEN US HOLDCO CORPORATION
Reel/Frame 061365/0688 →
CHANGE OF NAME Recorded Sep 1, 2022
From: GARDEN US HOLDCO CORPORATION
To: NEOGEN FOOD SAFETY US HOLDCO CORPORATION
Reel/Frame 061370/0437 →
Continuity (3)
Continuation 14008905
Provisional Application 61469355 · Mar 30, 2011
Related Publication 20160340709A1 · Nov 24, 2016