Granted Patent
B2
US 12,491,249 · App. 17/469,799 · Granted Dec 9, 2025
Methods for manufacturing phthalocyanine dye conjugates and stable conjugates
Inventors:
Lewis R. Makings (Encinitas, CA); Roger Heim (Del Mar, CA); Miguel Garcia-Guzman (San Diego, CA)
Assignee:
Rakuten Medical, Inc.
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Abstract
Provided are methods for manufacturing a conjugate containing a phthalocyanine dye, including methods that include one or more steps of preparing or producing the conjugate, formulating the conjugate and packaging the conjugate. In some aspects, the manufacturing methods result in the generation of a stable conjugate. Also provided are stable phthalocyanine dye conjugates, compositions and articles of manufacture containing the stable conjugates, and methods for their administration to subjects for photoimmunotherapy. In some embodiments, the phthalocyanine dye conjugates are conjugated to a targeting molecule, such as an antibody, that targets the conjugate to a cell or pathogen, such as by binding to a cell surface protein.
Claims (44)
1 . A pharmaceutical composition comprising:
a phthalocyanine dye conjugated to a targeting molecule, wherein the targeting molecule is an antibody or antibody fragment, wherein the phthalocyanine dye comprises the formula:
wherein:
L is a linker;
Q is a reactive group for attachment of the dye to the targeting molecule;
R 2 , R 3 , R 7 , and R 8 are each independently selected from among substituted alkyl and substituted aryl;
R 4 , R 5 , R 6 , R 9 , R 10 , and R 11 are each independently selected from among hydrogen, substituted alkyl, substituted alkanoyl, substituted alkoxycarbonyl, substituted alkylcarbamoyl, and a chelating ligand, wherein at least one of R 4 , R 5 , R 6 , R 9 , R 10 , and R 11 comprises a water soluble group;
R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 and R 23 are each independently selected from among hydrogen, halogen, substituted alkylthio, substituted alkylamino and substituted alkoxy; and
X 2 and X 3 are each independently C 1 -C 10 alkylene; and
wherein the pharmaceutical composition comprises greater than or equal to 92% monomer of the phthalocyanine dye conjugated to the antibody or antibody fragment when stored for at least 24 hours.
2 . The pharmaceutical composition of claim 1 , wherein the water soluble group is selected from the group consisting of a carboxylate (—CO 2 − ) group, a sulfonate (—SO 3 − ) group, a sulfonyl (—SO 2 − ) group, a sulfate (—SO 4 −2 ) group, a hydroxyl (—OH) group, a phosphate (—OPO 3 −2 ) group, a phosphonate (—PO 3 −2 ) group, an amine (—NH 2 ) group and a substituted quaternized nitrogen with each having a counter ion.
3 . The pharmaceutical composition of claim 1 , wherein the phthalocyanine dye is IRDye 700DX (IR700).
4 . The pharmaceutical composition of claim 1 , wherein the pharmaceutical composition further comprises one or more of the following features:
(a) less than or equal to 3% free dye,
(b) high molecular weight species less than or equal to 5%, and
(c) low molecular weight species less than or equal to 5%.
5 . The pharmaceutical composition of claim 1 , wherein the pharmaceutical composition comprises the following features:
(a) less than or equal to 3% free dye,
(b) high molecular weight species less than or equal to 5%,
(c) low molecular weight species less than or equal to 5%, and
(d) greater than or equal to 92% monomer.
6 . The pharmaceutical composition of claim 1 , wherein the targeting molecule binds to a cell surface target molecule selected from among cell membrane phospholipids, prokaryotic peptidoglycans, bacterial cell envelop proteins, viral capsid proteins, ACTHR, endothelial cell Anxa-1, aminopeptidase N, IL-6R, alpha-4-integrin, alpha-5-beta-3 integrin, alpha-5-beta-5 integrin, alpha-fetoprotein (AFP), ANPA, ANPB, APA, APN, APP, 1AR, 2AR, AT1, B1, B2, BAGE1, BAGE2, B-cell receptor BB1, BB2, BB4, calcitonin receptor, cancer antigen 125 (CA 125), CCK1, CCK2, CD5, CD10, CD11a, CD13, CD14, CD19, CD20, CD22, CD25, CD30, CD33, CD38, CD45, CD52, CD56, CD68, CD90, CD133, CD7, CD15, CD34, CD44, CD206, CD271, CEA (CarcinoEmbryonic Antigen), CGRP, chemokine receptors, cell-surface annexin-1, cell-surface plectin-1, Cripto-1, CRLR, CXCR2, CXCR4, DCC, DLL3, E2 glycoprotein, EGFR, EGFRVIII, EMR1, Endosialin, EP2, EP4, EpCAM, EphA2, ET receptors, Fibronectin, Fibronectin ED-B, FGFR, frizzled receptors, GAGE1, GAGE2, GAGE3, GAGE4, GAGE5, GAGE6, GLP-1 receptor, G-protein coupled receptors of the Family A (Rhodopsin-like), G-protein coupled receptors of the Family B (Secretin receptor-like), G-protein coupled receptors of the Family C (Metabotropic Glutamate Receptor-like), GD2, GP100, GP120, Glypican-3, hemagglutinin, Heparin sulfates, HER1, HER2, HER3, HER4, HMFG, HPV 16/18 and E6/E7 antigens, hTERT, IL11-R, IL-13R, ITGAM, Kalikrien-9, Lewis Y, LH receptor, LHRH-R, LPA1, MAC-1, MAGE 1, MAGE 2, MAGE 3, MAGE 4, MART1, MC1R, Mesothelin, MUC1, MUC16, Neu (cell-surface Nucleolin), Neprilysin, Neuropilin-1, Neuropilin-2, NG2, NK1, NK2, NK3, NMB-R, Notch-1, NY-ESO-1, OT-R, mutant p53, p97 melanoma antigen, NTR2, NTR3, p32 (p32/gC1q-R/HABP1), p75, PAC1, PAR1, Patched (PTCH), PDGFR, PDFG receptors, PDT, Protease-cleaved collagen IV, proteinase 3, prohibitin, protein tyrosine kinase 7, PSA, PSMA, purinergic P2X family, P2X1-5, mutant Ras, RAMP1, RAMP2, RAMP3 patched, RET receptor, plexins, smoothened, sst1, sst2A, sst2B, sst3, sst4, sst5, substance P, TEMs, T-cell CD3 Receptor, TAG72, TGFBR1, TGFBR2, Tie-1, Tie-2, Trk-A, Trk-B, Trk-C, TR1, TRPA, TRPC, TRPV, TRPM, TRPML, TRPP, TRPV1-6, TRPA1, TRPC1-7, TRPM1-8, TRPP1-5, TRPML1-3, TSH receptor, VEGF receptors, voltage-gated ion channels, VPAC1, VPAC2, Wilms tumor 1, Y1, Y2, Y4, and Y5.
7 . The pharmaceutical composition of claim 1 , wherein the targeting molecule is an antibody or an antibody fragment that binds EGFR.
8 . The pharmaceutical composition of claim 7 , wherein the targeting molecule is cetuximab or an antigen-binding fragment thereof.
9 . The pharmaceutical composition of claim 1 , wherein the targeting molecule is an antibody or an antibody fragment that binds PD-L1.
10 . The pharmaceutical composition of claim 4 , wherein the targeting molecule is an antibody or an antibody fragment that binds PD-L1.
11 . The pharmaceutical composition of claim 5 , wherein the targeting molecule is an antibody or an antibody fragment that binds PD-L1.
12 . The pharmaceutical composition of claim 11 , wherein the phthalocyanine dye comprises IRDye 700DX (IR700).
13 . A pharmaceutical composition comprising:
a phthalocyanine dye conjugated to a targeting molecule, wherein the targeting molecule is cetuximab, wherein the phthalocyanine dye comprises IRDye 700DX (IR700), and wherein the pharmaceutical composition comprises greater than or equal to 92% monomer of the phthalocyanine dye conjugated to cetuximab when stored for at least 24 hours.
14 . The pharmaceutical composition of claim 13 , wherein the pharmaceutical composition further comprises one or more of the following features:
(a) less than or equal to 3% free dye,
(b) high molecular weight species less than or equal to 5%, and
(c) low molecular weight species less than or equal to 5%.
15 . The pharmaceutical composition of claim 13 , wherein the pharmaceutical composition comprises the following features:
(a) less than or equal to 3% free dye,
(b) high molecular weight species less than or equal to 5%,
(c) low molecular weight species less than or equal to 5%, and
(d) greater than or equal to 92% monomer.
16 . The pharmaceutical composition of claim 1 , wherein greater than or equal to 92% of the phthalocyanine dye conjugated to the antibody or antibody fragment remains as the monomer for at least 3 months at a temperature of less than 30° C.
17 . A packaged pharmaceutical product comprising the pharmaceutical composition of claim 1 , and a container, wherein the container protects the pharmaceutical composition from transmission of light such that the percentage of light transmission is less than 50%.
18 . The packaged pharmaceutical product of claim 17 , wherein the container protects from transmission of light such that the percentage of light transmission is less than 10%.
19 . The packaged pharmaceutical product of claim 17 , wherein the container protects from transmission of light having a wavelength between about 250 nm and 800 nm.
20 . The packaged pharmaceutical product of claim 17 , wherein the container is green, blue, amber, translucent, opaque, or is wrapped in an opaque material.
Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Oct 18, 2021
From: MAKINGS, LEWIS R.; HEIM, ROGER; GARCIA-GUZMAN, MIGUEL; CHIN, EILEEN SUN; YADAV, DEEPAK; FONG, JERRY
To: RAKUTEN MEDICAL, INC.
Reel/Frame 057825/0237 →
Continuity (3)
Continuation
15753151
Provisional Application
62206774
· Aug 18, 2015
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