# US 10,307,489 B2 · Organic anion transporting peptide-based cancer imaging and therapy > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,307,489 B2 - Document ID: US10307489B2 - Status: Granted - Kind: B2 - Application number: 15/538,359 - Filed: 2015-12-22 - Published: 2017-12-21 - Granted: 2019-06-04 - Earliest claimed: 2014-12-22 - Applicants: Da Zen Theranostics, Inc. - Inventors: Leland W. K. Chung - Web page: https://patentgrep.com/patent/US10307489B2 ## CPC - A61K 47/558: {the modifying agent being a chemiluminescent acceptor} - A61K 51/0446: {having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil} - A61P 35/00: Antineoplastic agents - C09B 23/0066: {the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)} - G01N 33/57557: {of other specific parts of the body, e.g. brain} - A61K 49/0017: {Fluorescence in vivo} - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P) - G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q) ## Abstract A dye-drug conjugate for preventing, treating, or imaging cancer having the following structure: wherein R1 and R2 are independently selected from the group consisting of —H, alkyl, alkyl-sulphonate, alkylcarboxylic, alkylamino, aryl, —SO3H, —PO3H, —OH, —NH2, and -halogen; wherein Y1 and Y2 is independently selected from the group consisting of alkyl, aryl, aralkyl, alkylsulphonate, alkylcarboxylic, alkylamino, ω-alkylaminium, ω-alkynyl, PEGyl, PEGylcarboxylate, ω-PEGylaminium, ω-acyl-NH, ω-acyl-lysinyl-, ω-acyl-triazole, ω-PEGylcarboxyl-NH—, ω-PEGylcarboxyl-lysinyl, and ω-PEGylcarboxyl-triazole; wherein X is selected from the group consisting of a hydrogen, halogen, CN, Me, NH2, SH and OH; and R3 and R4 are independently a hydrogen, a therapeutic agent, or an imaging moiety, wherein the therapeutic agent is selected from the group consisting of a platinum-based therapeutic agent, a small molecule therapeutic agent, a peptide, a protein, a polymer, an siRNA, a microRNA, and a nanoparticle, wherein the imaging is a radio-isotope selected from the group consisting of F18, I-125, I-124 I-123, I-131, and small molecule labeled with any of these isotopes, or wherein the imaging moiety is a chelator-complexed radioactive isotope, wherein the radioactive isotope is selected from the group consisting of Cu-64, In-111, Tc-99m, Ga-68, Lu-177, Zo-89, Th-227 and Gd-157. ## Claims ### Claim 1 A method for diagnosing, detecting or treating a brain tumor, or a brain metastase of a cancer, comprising the step of administering to a subject suffering or suspected to suffer from a brain tumor or brain metastase, an effective amount of a dye-drug conjugate, and optionally imaging the subject or a sample of the subject, wherein the dye-drug conjugate comprises the following structure: wherein R1 and R2 are independently selected from the group consisting of —H, alkyl, alkyl-sulphonate, alkylcarboxylic, alkylamino, aryl, —SO3H, —PO3H, —OH, —NH2, and -halogen; wherein Y1 and Y2 are independently selected from the group consisting of alkylsulphonate, alkylcarboxylic, and alkylamino; wherein X is halogen; wherein one of R3 and R4 is hydrogen and is connected to an alkylsulphonate Y1 or Y2 moiety, and wherein the other of R3 and R4 is a therapeutic agent connected to an alkylcarboxylic Y1 or Y2 moiety, or to an alkylamino Y1 or Y2 moiety, and wherein the therapeutic agent is selected from the group consisting of gemcitabine, and a platin-based therapeutic agent. ### Claim 2 (depends on 1) The method according to claim 1, wherein the cancer is one selected from the group consisting of prostate cancer, breast cancer, renal cancer, pancreatic cancer, lung cancer, and hepatic cancer. ### Claim 3 (depends on 1) The method according to claim 1, wherein one of R3 and R4 is hydrogen and the other one of R3 and R4 is gemcitabine conjugated to one of Y1 and Y2. ### Claim 4 (depends on 1) The method according to claim 1, wherein one of R3 and R4 is hydrogen and the other one of R3 and R4 is gemcitabine connected to an alkylcarboxylic Y1 or Y2 moiety. ### Claim 5 (depends on 1) The method according to claim 1, wherein one of R3 and R4 is hydrogen and the other one of R3 and R4 is gemcitabine connected to an alkylamino Y1 or Y2 moiety. ### Claim 6 (depends on 1) The method according to claim 1, wherein one of R3 and R4 is hydrogen and the other one of R3 and R4 is a platin-based therapeutic agent conjugated to Y1 and Y2. ### Claim 7 (depends on 1) The method according to claim 1, wherein one of R3 and R4 is hydrogen and the other one of R3 and R4 is a platin-based therapeutic agent connected to an alkylcarboxylic Y1 or Y2 moiety. ### Claim 8 (depends on 1) The method according to claim 1, wherein one of R3 and R4 is hydrogen and the other one of R3 and R4 is a platin-based therapeutic agent connected to an alkylamino Y1 or Y2 moiety. ### Claim 9 (depends on 6) The method according to claim 6, wherein the platin-based therapeutic agent is selected from the group consisting of cisplatin, carboplatin, oxaliplatin, satraplatin, picoplatin and one or more derivative thereof. ### Claim 10 (depends on 7) The method according to claim 7, wherein the platin-based therapeutic agent is selected from the group consisting of cisplatin, carboplatin, oxaliplatin, satraplatin, picoplatin and one or more derivative thereof. ### Claim 11 (depends on 8) The method according to claim 8, wherein the platin-based therapeutic agent is selected from the group consisting of cisplatin, carboplatin, oxaliplatin, satraplatin, picoplatin and one or more derivative thereof. ### Claim 12 (depends on 1) The method according to claim 1, wherein the dye-drug conjugate is selected from one or more of the compounds designated DZ-2, DZ-3, DZ-6, DZ-7, as depicted in the formulae below: ### Claim 13 (depends on 1) The method according to claim 1, wherein the dye-drug conjugate is DZ-2. ### Claim 14 (depends on 1) The method according to claim 1, wherein the dye-drug conjugate is DZ-3. ### Claim 15 (depends on 1) The method according to claim 1; wherein the dye-drug conjugate is DZ-6. ### Claim 16 (depends on 1) The method according to claim 1, wherein the dye-drug conjugate is DZ-7. ### Claim 17 A method for diagnosing, detecting or treating a brain tumor, or a brain metastase of a cancer, comprising the step of administering to a subject suffering or suspected to suffer from a brain tumor or brain metastase, or to a sample of the subject, an effective amount of a dye-drug conjugate, and optionally imaging the subject or sample of the subject, wherein the dye-drug conjugate comprises the following structure: wherein R1 and R2 are independently selected from the group consisting of —H, alkyl, alkyl-sulphonate, alkylcarboxylic, alkylamino, aryl, —SO3H, —PO3H, —OH, —NH2, and -halogen; wherein Y1 and Y2 are independently selected from the group consisting of alkylsulphonate, alkylcarboxylic, and alkylamino; wherein X is halogen; wherein one of R3 and R4 is hydrogen and is connected to an alkylsulphonate Y1 or Y2 moiety, and wherein the other of R3 and R4 is a therapeutic agent connected to an alkylcarboxylic Y1 or Y2 moiety, or to an alkylamino Y1 or Y2 moiety, wherein the therapeutic agent is a platin-based therapeutic agent, and wherein the dye-drug conjugate is DZ-6 as depicted in the formulae below: ### Claim 18 (depends on 17) The method according to claim 17, wherein the cancer is one selected from the group consisting of prostate cancer, breast cancer, renal cancer, pancreatic cancer, lung cancer, and hepatic cancer.