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US 2021/0230428 A1Published application
Polymeric dyes and uses thereof
AssigneeBecton, Dickinson and Company
InventorJames R. Petisce
Life of this patent
Estimating the term…
Abstract
Disclosed herein are polymeric dyes, their preparation, and their uses. Some embodiments relate to their use for detecting biological activity in samples, such as the presence of bacteria in blood.
Claims54
A polymeric dye comprising:
- one or more fluorophores;
- and
- a polysiloxane composed of monomers A and B, optionally of monomer D, and two termini selected from the group consisting of —OR4 and R4, wherein:
- A has the structure —Si(R1)(R2)O—, B has the structure —Si(R3)(L)O—, and D has the structure —Si(R15)(R16)O—;
- R1, R2, R3, and R15 are each independently selected from the group consisting of C1-6 alkyl and C6-10 aryl;
- L is a linker selected from the group consisting of —(CH2)mNHC(═O)—, —(CH2)mNHC(═O)NH—, —(CH2)mNHC(═S)NH—, —(CH2)mNHS(O2)—, —(CH2)mNHC(═O)O—, —(CH2)mOC(═O)—, —(CH2)mNHC(═O)(CH2)nNHC(═O)—, —(CH2)mNHC(═O)(CH2)nNHC(═O)NH—, (CH2)mNHC(═O)(CH2)nNHC(═S)NH—, —(CH2)mNHC(═O)(CH2)nNHS(O2)—, —(CH2)mNHC(═O)(CH2)nNHC(═O)O—, —(CH2)mNHC(═O)(CH2)nC(═O)O— —(CH2)mC(═O)NH(CH2)nNHC(═O)—, —(CH2)mC(═O)NH(CH2)nNHC(═O)NH—, —(CH2)mC(═O)NH(CH2)nNHC(═S)NH—, —(CH2)mC(═O)NH(CH2)nNHS(O2)—, —(CH2)mC(═O)NH(CH2)nNHC(═O)O—, —(CH2)mC(═O)NH(CH2)nC(═O)O—, —(CH2)mOC(═O)(CH2)nNHC(═O)—, —(CH2)mOC(═O)(CH2)nNHC(═O)NH—, —(CH2)mOC(═O)(CH2)nNHC(═S)NH—, —(CH2)mOC(═O)(CH2)nNHS(O2)—, —(CH2)mOC(═O)(CH2)nNHC(═O)O—, —(CH2)mOC(═O)(CH2)nC(═O)O—, (CH2)mC(═O)O(CH2)nNHC(═O)—, —(CH2)mC(═O)O(CH2)nNHC(═O)NH—, —(CH2)mC(═O)O(CH2)nNHC(═S)NH—, —(CH2)mC(═O)O(CH2)nNHS(O2)—, —(CH2)mC(═O)O(CH2)nNHC(═O)O—, —(CH2)mC(═O)O(CH2)nC(═O)O—, (CH2)mNHC(═O)O(CH2)nNHC(═O)—, (CH2)mNHC(═O)O(CH2)nNHC(═O)NH—, (CH2)mNHC(═O)O(CH2)nNHC(═S)NH—, —(CH2)mNHC(═O)O(CH2)nNHS(O2)—, —(CH2)mNHC(═O)O(CH2)nNHC(═O)O—, —(CH2)mNHC(═O)O(CH2)nC(═O)O—, —(CH2)mOC(═O)NH(CH2)nNHC(═O)—, (CH2)mOC(═O)NH(CH2)nNHC(═O)NH—, (CH2)mOC(═O)NH(CH2)nNHC(═S)NH—, —(CH2)mOC(═O)NH(CH2)nNHS(O2)—, —(CH2)mOC(═O)NH(CH2)nNHC(═O)O—, —(CH2)mOC(═O)NH(CH2)nC(═O)O—, —(CH2)mS(CH2)nNHC(═O)—, —(CH2)mS(CH2)nNHC(═O)NH—, (CH2)mS(CH2)nNHC(═S)NH—, —(CH2)mS(CH2)nNHS(O2)—,
- wherein m and n are each independently an integer from 1 to 5, and wherein L provides a covalent linkage to the one or more fluorophores;
- each R4 is independently selected from the group consisting of H, —SH, halo, C6-10 aryl, C1-6 alkenyl,
- and C1-6 alkyl optionally substituted with one or more R5, —OC(═O)R6, —NR7R8, —NR9C(═O)R10, and —NRuC(═O)NR12R13, wherein q is an integer from 1 to 5;
- R5 is —OH or —SH;
- R6, R7, R8, R9, R10, R11, R12, and R13 are each independently hydrogen or each independently selected from the group consisting of C1-6 alkyl, phenyl, and C1-6 alkenyl, each optionally substituted with —OH, halo, —CN, C1-6 alkoxy, and —NH2;
- and
- R16 is
- wherein s is an integer from 1 to 5.
11 more elements
A polymeric dye comprising:
- one or more rhodamine fluorophores;
- and
- covalently bonded to the one or more rhodamine fluorophores, a polymer selected from the group consisting of polysiloxane, polypropylene, poly(t-butyl methacrylate), fluorinated ethylene propylene, hexatriacontane, poly(tetrafluoroethylene), poly(hexafluoropropylene), and polyisobutylene, or a functionalized derivative thereof.
A method of making a polymeric dye, comprising:
- obtaining a polysiloxane composed of monomers A and C, and optionally of monomer D, wherein:
- A has the structure —Si(R1)(R2)O—, C has the structure —Si(R14)(M)O—, and D has the structure —Si(R15)(R16)O—;
- R1, R2, R14, and R15 are each independently selected from the group consisting of C1-6 alkyl and C6-10 aryl;
- moiety M is selected from the group consisting of —(CH2)oNH2, —(CH2)oSH, and —(CH2)oNHC(═O)(CH2)pNH2, wherein o and p are each independently an integer from 1 to 5;
- R16 is
- wherein s is an integer from 1 to 5;
- B is present in about 0.5 to 5 mol %;
- and
- the number average molar mass of the polysiloxane is about 1000 to 3000 Dalton;
- obtaining a rhodamine fluorophore;
- and
- reacting the polysiloxane with the rhodamine fluorophore to form a covalent bond between the polysiloxane and the rhodamine fluorophore.
9 more elements
A method of making a sensor polymer for detecting biological activity, comprising:
- obtaining the polymeric dye;
- obtaining siloxane monomer;
- dissolving the polymeric dye and siloxane monomer to form a polymerization solution;
- subjecting the polymerization solution to appropriate conditions to form a polymeric dye entrapped within or covalently bonded to a polysiloxane.
1 more element
Dependencies are inferred from the claim text.