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US 2026/0193231 A1Published application
Quaternary ammonium cyanine dyes
AssigneesGeorgia State University Research Foundation, Inc., The Board of Regents of the University of Oklahoma
InventorsMaged HENARY, Emmanuel Ramsey BUABENG, Lacey R. MCNALLY
Life of this patent
Estimating the term…
Abstract
Disclosed herein are quaternary ammonium cyanine dyes. The dyes exhibit different absorption/emission profiles at different pH levels. The compounds can be used to detect Lewis acidic species, including metal ions and protons, for instance as pH probes. The compounds can be used as agents for biological assays, including diagnostics like optical, fluorescent, and optoacoustic imaging, especially in the detection of cancerous and other unhealthy cells.
Claims21
1-117. (canceled)
A compound having the formula:
- wherein
- Z1 is N—Rna and Z2 is O, S, C(Rz2)2, NRna, N═CRz2, or C(Rz2)═C(Rz2);
- or Z1 is null and Z2 is Z*—N(Rna)—, wherein:
- Z* is N═CRz2, C(Rz2)═C(Rz2);
- O, S, or C(Rz2)2;
- Rna is in each case independently selected from C1-8alkyl, optionally substituted one or more times by aryl, heteroaryl, COOH, OH, NH2, NHCH3, N(CH3)2, N(CH3)3, PO3H2, SO3H,
- Rz2 is in case independently selected from F, Cl, Br, I, NO2, CN, Rz2*, ORz2*, N(Rz2*)2, SO3Rz2, SO2Rz2*, SO2N(Rz2*)2, C(O)Rz2*;
- C(O)ORz2*, OC(O)Rz2*;
- C(O)N(Rz2*)2, N(Rz2*)C(O)Rz2, OC(O)N(Rz2*)2, N(Rz2*)C(O)N(Rz2*)2, wherein Rz2* is in each case independently selected from hydrogen, C1-8alkyl, aryl, C1-8heteroaryl, C3-8cycloalkyl, or C1-8 heterocyclyl;
- Z3 is N—Rnb and Z4 is O, S, C(Rz4)2, NRnb, N═CRz4, or C(Rz4)═C(Rz4);
- or Z3 is null and Z4 is Z*—N(Rnb)—, wherein:
- Z* is N═CRz4, C(Rz4)═C(Rz4), O, S, or C(Rz4)2;
- Rnb is in case independently selected from C1-8alkyl, optionally substituted one or more times by aryl, heteroaryl, COOH, OH, NH2, NHCH3, N(CH3)2, N(CH3)3, PO3H2, SO3H;
- Rz4 is in case independently selected from F, Cl, Br, I, NO2, CN, Rz4, ORz4, N(Rz4*)2, SO3Rz4, SO2Rz4, SO2N(Rz4*)2, C(O)Rz4;
- C(O)ORz4*, OC(O)Rz4*;
- C(O)N(Rz4*)2, N(Rz4*)C(O)Rz4*, OC(O)N(Rz4*)2, N(Rz4*)C(O)N(Rz4*)2, wherein Rz4* is in each case independently selected from hydrogen, C1-8alkyl, aryl, C1-8heteroaryl, C3-8cycloalkyl, or C1-8 heterocyclyl;
- R1a is F, Cl, Br, I, NO2, CN, R1a*, OR1a*, SR1a*, N(R1a*)2, SO3R1a*, SO2R1a*, SO2N(R1a*)2, C(O)R1a*;
- C(O)OR1a*, OC(O) R1a*;
- C(O)N(R1a*)2, N(R1a*)C(O)R1a*, OC(O)N(R1a*)2, N(R1a*)C(O)N(R1a*)2, wherein R1a* is in each case independently selected from hydrogen, C1-8alkyl, aryl, C1-8heteroaryl, C3-8cycloalkyl, or C1-8heterocyclyl;
- R2a is F, Cl, Br, I, NO2, CN, R2a*, OR2a*, SR2a*, N(R2a*)2, SO3R2a*, SO2R2a*, SO2N(R2a*)2, C(O)R2a*;
- C(O)OR2a*, OC(O)R2a*;
- C(O)N(R2a*)2, N(R2a*)C(O)R2a*, OC(O)N(R2a*)2, N(R2a*)C(O)N(R2a*)2, wherein R2a* is in each case independently selected from hydrogen, C1-8alkyl, aryl, C1-8heteroaryl, C3-8cycloalkyl, or C1-8heterocyclyl;
- R3a is F, Cl, Br, I, NO2, CN, R3a*, OR3a*, SR3a*, N(R3a*)2, SO3R3a*, SO2R3a*, SO2N(R3a*)2, C(O)R3a*;
- C(O)OR3a*, OC(O)R3a*;
- C(O)N(R3a*)2, N(R3a*)C(O)R3a*, OC(O)N(R3a*)2, N(R3a*)C(O)N(R3a*)2, wherein R3a* is in each case independently selected from hydrogen, C1-8alkyl, aryl, C1-8heteroaryl, C3-8cycloalkyl, or C1-8heterocyclyl;
- R4a is F, Cl, Br, I, NO2, CN, R4a*, OR4a*, SR4a*, N(R4a*)2, SO3R4a*, SO2R4a*, SO2N(R4a*)2, C(O)R4a*;
- C(O)OR4a*, OC(O)R4a*;
- C(O)N(R4a*)2, N(R4a*)C(O)R4a*, OC(O)N(R4a*)2, N(R4a*)C(O)N(R4a*)2, wherein R4a* is in each case independently selected from hydrogen, C1-8alkyl, aryl, C1-8heteroaryl, C3-8cycloalkyl, or C1-8heterocyclyl;
- R1b is F, Cl, Br, I, NO2, CN, R1b*, OR1b*, SR1b*, N(R1b*)2, SO3R1b*, SO2R1b*, SO2N(R1b*)2, C(O)R1b*;
- C(O)OR1b*, OC(O) R1b*;
- C(O)N(R1b*)2, N(R1b*)C(O)R1b*, OC(O)N(R1b*)2, N(R1b*)C(O)N(R1b*)2, wherein R1b* is in each case independently selected from hydrogen, C1-8alkyl, aryl, C1-8heteroaryl, C3-8cycloalkyl, or C1-8heterocyclyl;
- R2b is F, Cl, Br, I, NO2, CN, R2b*, OR2b*, SR2b*, N(R2b*)2, SO3R2b*, SO2R2b*, SO2N(R2b*)2, C(O)R2b*;
- C(O)OR2b*, OC(O)R2b*;
- C(O)N(R2b*)2, N(R2b*)C(O)R2b*, OC(O)N(R2b*)2, N(R2b*)C(O)N(R2b*)2, wherein R2b* is in each case independently selected from hydrogen, C1-8alkyl, aryl, C1-8heteroaryl, C3-8cycloalkyl, or C1-8heterocyclyl;
- R3b is F, Cl, Br, I, NO2, CN, R3b*, OR3b*, SR3b*, N(R3b*)2, SO3R3b*, SO2R3b*, SO2N(R3b*)2, C(O)R3b*;
- C(O)OR3b*, OC(O)R3b*;
- C(O)N(R3b*)2, N(R3b*)C(O)R3b*, OC(O)N(R3b*)2, N(R3b*)C(O)N(R3b*)2, wherein R3b* is in each case independently selected from hydrogen, C1-8alkyl, aryl, C1-8heteroaryl, C3-8cycloalkyl, or C1-8heterocyclyl;
- R4b is F, Cl, Br, I, NO2, CN, R4b*, OR4b*, SR4b*, N(R4b*)2, SO3R4b*, SO2R4b*, SO2N(R4b*)2, C(O)R4b*;
- C(O)OR4b*, OC(O)R4b*;
- C(O)N(R4b*)2, N(R4b*)C(O)R4b*, OC(O)N(R4b*)2, N(R4b*)C(O)N(R4b*)2, wherein R4b* is in each case independently selected from hydrogen, C1-8alkyl, aryl, C1-8heteroaryl, C3-8cycloalkyl, or C1-8heterocyclyl;
- Ra is F, Cl, Br, I, NO2, CN, Ra*, ORa*, SRa*, N(Ra*)2, SO2Ra*, SO2N(Ra*)2, C(O)Ra*;
- C(O)ORa*, OC(O)Ra*;
- C(O)N(Ra*)2, N(Ra*)C(O)Ra*, OC(O)N(Ra*)2, N(Ra*)C(O)N(Ra*)2, wherein Ra* is in each case independently selected from hydrogen, C1-8alkyl, aryl, C1-8heteroaryl, C3-8cycloalkyl, or C1-8heterocyclyl;
- Rb is F, Cl, Br, I, NO2, CN, Rb*, ORb*, SRb*, N(Rb*)2, SO2Rb*, SO2N(Rb*)2, C(O)Rb*;
- C(O)ORb*, OC(O)Rb*;
- C(O)N(Rb*)2, N(Rb*)C(O)Rb*, OC(O)N(Rb*)2, N(Rb*)C(O)N(Rb*)2, wherein Rb* is in each case independently selected from hydrogen, C1-8alkyl, aryl, C1-8heteroaryl, C3-8cycloalkyl, or C1-8heterocyclyl;
- Rc is F, Cl, Br, I, NO2, CN, Rc*, ORc*, SRc*, N(Rc*)2, SO2Rc*, SO2N(Rc*)2, C(O)Rc*;
- C(O)ORc*, OC(O)Rc*;
- C(O)N(Rc*)2, N(Rc*)C(O)Rc*, OC(O)N(Rc*)2, N(Rc*)C(O)N(Rc*)2, wherein Rc* is in each case independently selected from hydrogen, C1-8alkyl, aryl, C1-8heteroaryl, C3-8cycloalkyl, or C1-8heterocyclyl;
- Rd is F, Cl, Br, I, NO2, CN, Rd*, ORd*, SRd*, N(Rd*)2, SO2Rd*, SO2N(Rd*)2, C(O)Rd*;
- C(O)ORd*, OC(O)Rd*;
- C(O)N(Rd*)2, N(Rd*)C(O)Rd*, OC(O)N(Rd*)2, N(Rd*)C(O)N(Rd*)2, wherein Rd* is in each case independently selected from hydrogen, C1-8alkyl, aryl, C1-8heteroaryl, C3-8cycloalkyl, or C1-8heterocyclyl;
- R1 and R2 are independently selected from H, C1-6alkyl, C2-6alkenyl, C2-6alkynyl aryl, C3-6 cycloalkyl, C1-6heterocyclyl, or C1-6heteroaryl, wherein R1 and R2 can together form a ring;
- wherein one or both of R1 and R2 are substituted with one or more groups selected from -Q-ORz, -Q-SRz, -Q-N(Rz)2, -Q-N(Rz′)3, ═O, -Q-CN, C1-6alkyl, aryl, halo, C1-6haloalkyl, C3-6cycloalkyl, C3-6heterocycloalkyl, -Q-SO2Rz, -Q-SO3Rz, -Q-C(O)Rz, -Q-C(O)ORz, -Q-C(O)N(Rz)2, wherein Rz is in each case independently selected from H, or C1-3alkyl, Rz′ is independently selected from C1-6alkyl, wherein any two or more of Rz and Rz′ can together form a ring;
- and Q is null or C1-4alkylene;
- with the proviso that when R1 is H, R2 is not phenyl;
- and
- R3 and R4 are independently selected from C1-3alkyl, and may together form a ring;
- wherein each is optionally substituted one or more times by -Q1-ORy, -Q1-N(Ry)2, -Q1-N(Ry′)3, ═O, aryl, -Q1-SO3Ry, -Q1-PO3(Ry)2, -Q1-C(O)Ry, -Q1-C(O)ORy, -Q1-C(O)N(Ry)2, wherein Ry is in each case independently selected from H, C1-6alkyl, Ry′ is independently selected from C1-3alkyl, wherein any two or more of Rz and Ry′ can together form a ring;
- and Q1 is null or C1-4alkylene.
57 more elements
Dependencies are inferred from the claim text.