US 12,092,643 B2
Detecting targets using mass tags and mass spectrometry
Christopher Bieniarz, Tucson, AZ (US); Jan Froehlich, Oro Valley, AZ (US); Brian Daniel Kelly, Tucson, AZ (US); Rui Hong, Oro Valley, AZ (US); Mark Lefever, Oro Valley, AZ (US); Phillip Miller, Tucson, AZ (US); and Hong Wang, Oro Valley, AZ (US)
Assigned to Ventana Medic Systems, Inc., Tucson, AZ (US)
Filed by Ventana Medical Systems, Inc., Tucson, AZ (US)
Filed on Sep. 15, 2020, as Appl. No. 17/021,659.
Application 17/021,659 is a division of application No. 16/055,046, filed on Aug. 4, 2018, granted, now 10,883,999.
Application 16/055,046 is a continuation of application No. 14/981,181, filed on Dec. 28, 2015, granted, now 10,078,083, issued on Sep. 18, 2018.
Application 14/981,181 is a continuation of application No. 13/805,983, filed on Jan. 25, 2013, granted, now 9,291,597, issued on Mar. 22, 2016.
Application 13/805,983 is a continuation of application No. PCT/US2011/042853, filed on Jul. 1, 2011.
Claims priority of provisional application 61/464,937, filed on Mar. 11, 2011.
Claims priority of provisional application 61/464,977, filed on Mar. 11, 2011.
Claims priority of provisional application 61/398,944, filed on Jul. 2, 2010.
Claims priority of provisional application 61/398,942, filed on Jul. 2, 2010.
Prior Publication US 2021/0063411 A1, Mar. 4, 2021
Int. Cl. G01N 33/68 (2006.01)
CPC G01N 33/6848 (2013.01) 18 Claims
 
1. A conjugate comprising having a formula:

OG Complex Work Unit Chemistry
wherein
the ‘Mass Tag Precursor’ is a nitrophenyl moiety or a heteroaryl moiety;
R16 is selected from ether, hydroxyl, —N(H)(R11) or —NH2;
R11 is selected from an aliphatic group having between 1 and 10 carbon atoms, a heteroaliphatic group having between 1 and 10 carbon atoms, an aryl group, a heteroaryl group;
R17 is selected from an aliphatic group having between 1 and 10 carbon atoms, a heteroaliphatic group having between 1 and 10 carbon atoms, an aryl group having 5 or 6 carbon atoms, or a heteroaryl group having 4 or 5 carbon atoms;
n is an integer ranging from 1 to 20;
Y is selected from oxygen, sulfur, or —N(R11)—, or —NH—;
the optional linker is selected from an aliphatic group, a heteroaliphatic group, or heterobifunctional linkers; and
the optional carrier is selected from a polymer, a biomolecule, a liposome, a micelle, or a nanoparticle;
wherein the nitrophenyl moiety has the formula:

OG Complex Work Unit Chemistry
where R22, R23, and R24 are independently selected from an aliphatic group, a heteroaliphatic group, an aryl group, a heteroaryl group, a carbonyl group, a halogen, a hydrogen, a hydroxyl group, an isothiocyanate group, an isocyanate group, a nitrile group, a nitro group, a thiol, or any combination thereof, at least one of R22, R23, and R24 is nitro;
Y is selected from oxygen, sulfur, or -(nitrogen —R11)—;
R7 is selected from aliphatic or heteroaliphatic;
R8 is selected from an aliphatic group, a heteroaliphatic group, a heterobifunctional linker, a charged moiety, a chromophore, or any combination thereof; and
R11 is an aliphatic group, a heteroaliphatic group, an aryl group, or a heteroaryl group; and
wherein the heteroaryl moiety has a formula:

OG Complex Work Unit Chemistry
where R25, R26, and R28 are independently selected from carbon or nitrogen, where at least one of R25, R26, R27, and R28 is nitrogen;
each Y is independently selected from oxygen, sulfur, or -(nitrogen —R11)—;
R8 comprises an aliphatic group, a heteroaliphatic group, a heterobifunctional linker, a charged moiety, a chromophore, or any combination thereof; and
R11 is an aliphatic group, a heteroaliphatic group, an aryl group, or a heteroaryl group.