Chemistry: natural resins or derivatives; peptides or proteins; – Proteins – i.e. – more than 100 amino acid residues – Chemical modification or the reaction product thereof – e.g.,...
Reexamination Certificate
2008-04-01
2008-04-01
Tucker, Zachary C (Department: 1624)
Chemistry: natural resins or derivatives; peptides or proteins;
Proteins, i.e., more than 100 amino acid residues
Chemical modification or the reaction product thereof, e.g.,...
C530S391900, C544S277000, C544S405000, C546S103000, C546S104000, C546S108000, C546S148000, C546S176000, C546S270100, C548S156000
Reexamination Certificate
active
07351807
ABSTRACT:
Dye-sulfenate derivatives and their bioconjugates for dual phototherapy of tumors and other lesions. The compounds comprise sulfenates having the formula, t,0080where E is selected from the group consisting of somatostatin receptor binding molecules, heat sensitive bacterioendotoxin receptor binding molecules, neurotensin receptor binding molecules, bombesin receptor binding molecules, cholecystekinin receptor binding molecules, steroid receptor binding molecules, and carbohydrate receptor binding molecules, and dihydoxyindolecarboxylic acid; L and X are independently selected from the group consisting of —(R5)NOC—, —(R5)NOCCH2O—, —(R5)NOCCH2CH2O—, —OCN(R5)—, —HNC(═S)NH—, and HNC(═O)NH—; DYE is an aromatic or a heteroaromatic radical derived from the group consisting of cyanines, indocyanines, phthalocyanines, rhodamines, phenoxazines, phenothiazines, phenoselenazines, fluoresceins, porphyrins, benzoporphyrins, squaraines, corrins, croconiums, azo dyes, methine dyes, indolenium dyes, crellins, and hypocrellins; R1to R5are independently selected from the group comprising hydrogen, C1-C10 alkyl, C5-C10 aryl, C1-C10 polyhydroxyalkyl, and C1-C10 polyalkoxyalkyl; and Ar is an aromatic or heteroaromatic radical derived from the group consisting of benzenes, naphthalenes, naphthoquinones, diphenylmethanes, fluorenes, anthracenes, anthraquinones, phenanthrenes, tetracenes, naphthacenediones, pyridines, quinolines, isoquinolines, indoles, isoindoles, pyrroles, imidiazoles, oxazoles, thiazoles, pyrazoles, pyrazines, purines, benzimidazoles, furans, benzofurans, dibenzofurans, carbazoles, acridines, acridones, phenanthridines, thiophenes, benzothiophenes, dibenzothiophenes, xanthenes, xanthones, flavones, coumarins, and anthacylines. The compounds are designed to produce both Type 1 and Type 2 phototherapeutic effects at once using a dual wavelength light source that will produce singlet oxygen and free radicals at the lesion of interest.
REFERENCES:
patent: 2929824 (1960-03-01), Kharasch et al.
patent: 5518888 (1996-05-01), Waldman
patent: 5714342 (1998-02-01), Komoriya et al.
patent: WO 00/41727 (2000-07-01), None
Chemical Abstracts Registry No. 523-42-2, 2002.
Hawley, Gessner, “The Condensed Chemical Dictonary”, 1977, Van Nostrand, New York, pp. 244.
Chemical Abstracts, Registry diethylthiadicarbocyanine iodide 2002.
LaRive, H. et al, Chemistry of heterocyclic Compounds, vol. 34, pt.3, 1979, pp. 23-30.
S. Achilefu, Ph.D. et al.,Novel Receptor-Targeted Fluorescent Contrast Agents for In Vivo Tumor Imaging, Investigative Radiology, vol. 35, No. 8, 2000, 479-485.
Jerome Amaudrut et al.,The Thermal Sulfenate-Sulfoxide Rearrangement: A Radical Pair Mechanism, J. Amer. Chem, Soc. , vol. 122, 2000, 3367-3374.
A. Andreoni et alr,Tumour photosensitization by chemotherapeutic drugs, Biology, N3, 1993, 43-46.
Byron Ballou et al.,Tumor labeling in vivo using cyanine-conjugated monoclonal antibodies, Cancer Immunology and Immunotherapy, vol. 41, 1995, 257-263.
M.D. Daniell et al.,A History of Photodynamic Therapy, Aust. N.Z. J. Surg., vol. 61, 1991, 340-348.
T.J. Dougherty et al.,Photoradiation Therapy. II. Cure of Animal Tumors with Hematoporphyrin and Light, Journal of the National Cancer Institute, vol. 55, No. 1, 1975, 115-121.
G. Freiherr,The Light Stuff: Optical Imaging in Medical Diagnosis, Medical Device & Diagnositc Industry Magazine, 1998, 1-7.
M.R. Hamblin et al.,On the mechanism of the tumour-localising effect in photodynamic therapy, J. Photochem. Photobiol. B: Biol., vol. 23, 1994, 3-8.
J. C. Hebden et al.,Diagnostic imaging with light, The British Journal of Radiology, vol. 70, 1997, S206-S214.
D.J. Hnatowich et al.,Radioactive Labeling of Antibody: A Simple and Efficient Method, Science, vol. 220, 1983, 613-615.
G. Jori,Tumour photosensitizers: approaches to enhance the selectivity and efficiency of photodynamic therapy, Journal of Photochemistry and Photobiology B: Biology, vol. 36, 1996, 87-93.
G. Jori,Novel Therapeutic Modalities Based on Photosensitized Processes, EPA Newsletter, No. 60, 1997, 12-18.
G. Jori,Far-red-absorbing photosensitizers: their use in the photodynamic therapy of tumours, J. Photochem. Photobiol. A: Chem., vol. 62, 1992, 371-378.
G. Jori et al.,Second Generation Photosensitizers for the Photodynamic Therapy of Tumours, Light in Biology and Medicine, vol. 2, R.H. Douglas et al. (Eds.), 1991, 253-266.
M. Korbelik,Photosensitizers in photodynamic therapy, Periodicum Biologorum, vol. 93, No. 4, 1991, 563-574.
K. Licha et al.,New Contrast Agents for Optical Imaging: Acid-Cleavable Conjugates of Cyanine Dyes with Biomedicals, Part of the SPIE Conference on Molecular Imaging: Reporters, Dyes, and Instrumentation, Proceedings of SPIE, vol. 3600, 1999, 29-35.
R.L. Lipson, M.D. et al.,Hematoporphyrin Derivative for Detection and Management of Cancer, Cancer, vol. 20, No. 12, 1967, 2255-2257.
Y. Luo et al.,Rapid Initiation of Apoptosis by Photodynamic Therapy, Photochemistry and Photobiology, vol. 63, No. 4, 1996, 528-534.
K. Matsumura,1-Aminoacridine-4-carboxylic Acid, Journal of the American Chemical Society, vol. 60, (1938) 591-593.
G.G. Miller et al.,Preclinical Assessment of Hypocrellin B and Hypocrellin B Derivatives as Sensitizers for Photodynamic Therapy of Cancer: Progress Update, Photochemistry and Photobiology, vol. 65, No. 4, 1997, 714-722.
T. Parasassi et al.,Two-photon microscopy of aorta fibers shows proteolysis induced by LDL hydroperoxides, Free Radical in Biology and Medicine vol. 28, No. 11, 2000, 1589-1597.
D.J. Pasto et al.,Demonstration of the Synthetic Utility of the Generation of Alkoxy Radicals by the Proto-Induced, Homolytic Dissociation of Alkyl 4-Nitrobenzenesulfenates, Tetrahedron Letters, vol. 35, No. 25, 1994, 4303-4306.
A. Pelegrin et al.,Photoimmunodiagnosis with antibody-fluorescein conjugates: in vitro and in vivo preclinical studies, J. Cell Pharmacol, vol. 3, 1992, 141-145.
W. G. Roberts et al.,Role of Neovasculature and Vascular Permeability on the Tumor Retention of Photodynamic Agents, Cancer Research, vol. 52, 1992, 924-930.
G.I. Stables et al.,Photodynamic therapy, Cancer Treatment Reviews, vol. 21, 1995, 311-323.
T. Takemura et al. ,Mechanism of Photodynamic Therapy: Exploration by Photophysiocochemical Study, Frontiers of Photobiology, 1993, 503-506.
K.B. Trauner et al.,Photodynamic Synovectomy Using Benzoporphyrin Derivative in an Antigen-Induced Arthritis Model for Rheumatoid Arthritis., Photochemistry and Photobiology, vol. 67, No. 1, 1998, 133-139.
I.P.J. van Geel et al.,Photosensitizing Efficacy of MTHPC-PDT Compared to Photofrin-PDT in the RIF1 Mouse Tumour and Normal Skin, Int. J. Cancer, vol. 60, 1995, 388-394.
Kreimer-Birnbaum, Modified Porphyrins, Chlorins, Phthalocyanines, and Purpurins: Second-Generation Photosensitizers for Photodynamic Therapy, Seminars in Hematology, vol. 26, No. 2 (Apr. 1998), pp. 157-173 XP 000501369.
Delaney, et al., Photodynamic Therapy of Cancer, Comprehensive Therapy, 1988, vol. 14, No. 5, pp. 43-55 XP 000909044.
Pasto et al., Photolysis of Alkyl 4-Nitrobenzenesulfenates. A New and Versatile method for the Generation of Free Radicals, J. Org. Chem., 1990, vol. 55, pp. 5815-5816 XP 002353156.
Achilefu Samuel I.
Bugaj Joseph E.
Dorshow Richard B.
Rajagopalan Raghavan
Mallinckrodt Inc.
Thompson Hine LLP
Tucker Zachary C
LandOfFree
Cyanine-sulfenates for dual phototherapy does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Cyanine-sulfenates for dual phototherapy, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Cyanine-sulfenates for dual phototherapy will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2767197