Phthalocyanine dye compounds, conjugates and methods of use thereof

A conjugate comprising:

• i) a targeting molecule;
• and
• ii) compound of Formula (I):
• or a salt, stereoisomer, or tautomer thereof, wherein,
• M is Si;
• X is
• Y is
• R1 and R2 are each independently optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted heteroaryl, or optionally substituted heteroaralkyl;
• R3, R4 or R5 are selected from substituent group (a) or substituent group (b) wherein,
• (a) R3 is hydrogen, -L3-H, -L3-A, or -L3-Z;
• R4 is -L4-H, —(NH)m-L4-A, —(NH)m-L4-Z, —(O)m-L4-A or —(O)m-L4-Z;
• and
• R5 is -L5-H or -L5-A;
• and
• (b) R3 is -L3-H, or -L3-A;
• R4 is -L4-H, —(NH)m-L4-A, or —(O)m-L4-A;
• wherein R3 and R4 are connected with a bond to form a heterocyclyl substituted with -L4-A;
• and
• R5 is -L5-H or -L5-A;
• provided at least one of R3, R4 and R5 is a group containing A:
• A is a reactive group capable of forming a covalent bond with a thiol, hydroxyl, carboxyl or amino group of the targeting molecule, or a protected form thereof or a reacted form thereof;
• R6 and R7 are each independently optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted heteroaryl or optionally substituted heteroaralkyl;
• R8, R9 or R10 are selected from substituent group (a) or substituent group (b) wherein,
• (a) R8 is hydrogen, -Lg-H or -L8-Z;
• R9 is -L9-H, —(NH)n-L9-Z or —(O)n-L9-Z;
• and
• R10 is -L10-Z;
• and
• (b) Rg and R9 are connected with a bond to form a heterocyclyl substituted with -L9-Z and R10 is -L10-H or -L10-Z;
• provided at least one of R8, R9 and R10 is a group containing Z;
• Z is a water soluble group comprising one or more polar or ionic substituents selected from carboxylate (—CO2), poly(ethylene glycol), sulfonate (—SO3H) group, a sulfonyl (—SO2H) group, a sulfate (—SO4) group, a hydroxyl (—OH) group, a phosphate (—OPO3H) group, a phosphonate (—PO3H) group, an amine (—NH2) group, and quaternized nitrogen, each of which are optionally substituted with A or L′-A;
• L1 and L2 are each independently optionally substituted alkylene, optionally substituted heteroalkylene, optionally substituted alkenylene, optionally substituted heteroalkenylene, optionally substituted cycloalkyl, or optionally substituted heterocyclyl;
• L3, L4, L5, L8, L9 and L10 are each independently optionally substituted alkylene, optionally substituted heteroalkylene, optionally substituted alkenylene, optionally substituted heteroalkenylene, optionally substituted cycloalkylene, optionally substituted heterocyclene, optionally substituted arylene, optionally substituted aralkylene, optionally substituted heteroaralkylene, or optionally substituted heteroarylene, where the carbon atom of the alkylene, heteroalkylene, alkenylene, heteroalkenylene, cycloalkylene, heterocyclene, arylene, aralkylene, heteroaralkylene, or optionally substituted heteroarylene is further optionally substituted with Z and each nitrogen atom of the heteroalkylene or heteroalkenylene is optionally substituted with one or two L′-Z;
• L′ is each independently optionally substituted alkylene, optionally substituted heteroalkylene, optionally substituted alkenylene, optionally substituted heteroalkenylene, optionally substituted cycloalkylene, optionally substituted heterocyclene, optionally substituted arylene, optionally substituted aralkylene, optionally substituted heteroaralkylene, or optionally substituted heteroarylene;
• a is 0 or 1;
• b is 0 or 1;
• c is 0 or 1;
• d is 0 or 1;
• m is 0 or 1;
• n is 0 or 1;
• provided that if b is 1, then a is 0;
• if d is 1, then c is 0;
• if m is 1, b is 1;
• and
• if n is 1, c is 1;
• and
• provided that when R6 and R7 are both methyl, and L2 is propylene, c is 1 and d is 0, then L8, L9 and L10 are each not propylene;
• wherein the targeting molecule is covalently linked to the compound of Formula (I).