US 11,999,885 B2Granted

Hydroporphyrin beads with narrow fluorescence emissions

AssigneeNIRvana Sciences Inc.

InventorsJames Bruce Pitner, Rosemary B. Evans-Storms, Duane A. Olsen

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Abstract

Provided are fluorescent microparticles and/or nanoparticles that have a polymeric matrix and at least one porphyrinic macrocycle associated therewith. The porphyrinic macrocycles associated with the presently disclosed fluorescent microparticles and/or nanoparticles are in some embodiments selected from the group consisting of porphyrins (including 17,18-didehydrophorbines), chlorins (including phorbines), bacteriochlorins (including bacteriophorbines), and isobacteriochlorins (including isobacteriochlorins containing a fused “E” ring). In some embodiments, the porphyrinic macrocycles have structures selected from Formulas I and H. Also provided are populations made up of a plurality of distinct fluorescent microparticles and/or nanoparticles, methods of making and using the same, sets of separately detectable fluorescent microparticles and/or nanoparticles and methods for preparing and using the same, porphyrinic macrocycle-containing dyads conjugated to particles and methods for using the same to calibrate multi-laser flow cytometers, align and/or calibrate confocal fluorescence microscopes, and/or differentially labeling cells and/or other biomolecules, and biomolecules such as antibodies, fragments, and derivatives thereof covalently conjugated to the presently disclosed fluorescent microparticles and/or nanoparticles and/or to the presently disclosed porphyrinic macrocycle-containing dyads.

Claims11

Dependent claims

A fluorescent microparticle and/or nanoparticle, wherein the fluorescent microparticle and the fluorescent nanoparticle consists of a polystyrene bead and one or more fluorescent hydroporphyrins associated therewith, wherein each of the one or more fluorescent hydroporphyrins is selected from the group consisting of chlorins and bacteriochlorins, and wherein each of the one or more fluorescent hydroporphyrins has a structure selected from the group consisting of Formulas I and II:

wherein:
M is a metal or is absent;
X is selected from the group consisting of Se, NH, CH2, O and S;
and
R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocyclo, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkoxy, halo, mercapto, azido, cyano, formyl, carboxylic acid, hydroxyl, nitro, acyl, aryloxy, alkylthio, amino, alkylamino, arylalkylamino, disubstituted amino, acylamino, acyloxy, ester, amide, sulfoxyl, sulfonyl, sulfonate, sulfonic acid, sulfonamide, urea, alkoxylacylamino, aminoacyloxy, linking groups, and surface attachment groups;
K1, K2, K3, and K4 are hetero atoms independently selected from the group consisting of N, O, S, Se, Te, and CH;
and
S3, S4, S7, S8, S9, S10, S11, S12, S13, and S14, and either S1 and S5, or S2 and S6 are independently selected from the group consisting of H, aryl, phenyl, cycloalkyl, alkyl, alkenyl, alkynyl, halogen, alkoxy, alkylthio, perfluoroalkyl, perfluoroaryl, pyridyl, cyano, thiocyanato, nitro, amino, alkylamino, acyl, sulfoxyl, sulfonyl, imido, amido, and carbamoyl;
or S7 and S13 together form ═O.

6 more elements

A composition consisting of (a) an antibody, or a fragment or derivative thereof and (b) a fluorescent microparticle and/or a nanoparticle;

wherein the antibody, or a fragment or derivative thereof is covalently conjugated to the fluorescent microparticle and/or nanoparticle, and wherein the fluorescent microparticle and the fluorescent nanoparticle consists of a polystyrene bead and one or more fluorescent hydroporphyrins associated therewith, wherein each of the one or more fluorescent hydroporphyrins is selected from the group consisting of chlorins and bacteriochlorins, and wherein each of the one or more fluorescent hydroporphyrins has a structure selected from the group consisting of Formulas I and II:
wherein:
M is a metal or is absent;
X is selected from the group consisting of Se, NH, CH2, O and S;
and
R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocyclo, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkoxy, halo, mercapto, azido, cyano, formyl, carboxylic acid, hydroxyl, nitro, acyl, aryloxy, alkylthio, amino, alkylamino, arylalkylamino, disubstituted amino, acylamino, acyloxy, ester, amide, sulfoxyl, sulfonyl, sulfonate, sulfonic acid, sulfonamide, urea, alkoxylacylamino, aminoacyloxy, linking groups, and surface attachment groups;
K1, K2, K3, and K4 are hetero atoms independently selected from the group consisting of N, O, S, Se, Te, and CH;
and
S3, S4, S7, S8, S9, S10, S11, S12, S13, and S14, and either S1 and S5, or S2 and S6 are independently selected from the group consisting of H, aryl, phenyl, cycloalkyl, alkyl, alkenyl, alkynyl, halogen, alkoxy, alkylthio, perfluoroalkyl, perfluoroaryl, pyridyl, cyano, thiocyanato, nitro, amino, alkylamino, acyl, sulfoxyl, sulfonyl, imido, amido, and carbamoyl;
or S7 and S13 together form ═O.

7 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/308,285Filed 12 Jun 2017 · us provisional application
Priority: 10 Jun 2016
Published: US 2019/0264102 A129 Aug 2019
Granted: 4 Jun 2024
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

C09K 11/06
Luminescent materials, e.g. electroluminescent or chemiluminescent: containing organic luminescent materials
C09K 11/02
Luminescent materials, e.g. electroluminescent or chemiluminescent: use of particular materials as binders, particle coatings or suspension media…
G01N 21/64
Optically excited: fluorescence; Phosphorescence
C09K 2211/186
Metal complexes: of the light metals other than alkali metals and alkaline earth metals, i.e. Be, Al or Mg