Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – 25 or more amino acid residues in defined sequence
Reexamination Certificate
2006-03-20
2008-09-23
Lukton, David (Department: 1654)
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
25 or more amino acid residues in defined sequence
C530S399000, C604S020000, C606S002000, C558S062000, C562S125000
Reexamination Certificate
active
07427657
ABSTRACT:
The present invention discloses novel sulfenate derivatives and their bioconjugates for phototherapy of tumors and other lesions. The sulfenates of the present invention are designed to absorb low-energy ultraviolet, visible, or near-infrared (NIR) region of the electromagnetic spectrum. The phototherapeutic effect is caused by direct interaction of free radicals, the reactive intermediate produced upon photofragmentation of the sulfenate moiety, with the tissue of interest.
REFERENCES:
patent: 5518888 (1996-05-01), Waldman
patent: 5650292 (1997-07-01), Scherz et al.
patent: 5714342 (1998-02-01), Komoriya et al.
patent: 6462070 (2002-10-01), Hasan et al.
patent: 7230088 (2007-06-01), Rajagopalan et al.
patent: 7235685 (2007-06-01), Rajagopalan et al.
patent: 7267994 (2007-09-01), Meares et al.
patent: 7303926 (2007-12-01), Rajagopalan et al.
patent: 2003/0036538 (2003-02-01), Rajagopalan et al.
patent: 2003/0158127 (2003-08-01), Rajagopalan et al.
patent: 2004/0156783 (2004-08-01), Rajagopalan et al.
patent: 2006/0105974 (2006-05-01), Lange et al.
patent: 2006/0177457 (2006-08-01), Rajagopalan et al.
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.
Anderson Journal of Photochemistry and photobiology, B: Biology, 68(2-3):101-108, 2002.
A. Andreoni et al.,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.
Bonnett et al,Porphyrin Sensitizers in Tumour Phototherapy. Novel Sensitizers of the Chlorin and Bacteriochlorin Class with Amphiphilic Properties, Journal of Photochemistry and Photobiology, B: Biology, 6:29-37 (1990).
M.D. Daniel 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 wiht Hematoporphyrin and Light, Journal of the National Cancer Institute, vol. 55, No. 1, 1975, 115-121.
EPO,European Search Report, EP Application No. 02744398.5-2177, PCT/US0219185, mailed on Jan. 1, 2006.
G. Freiherr,The Light Stuff: Optical Imaging in Medical Diagnosis, Medical Device & Diagnositc Industry Magazine, 1998, 40-46.
Gluckman, Laryngoscope, 101(1 Pt 1):36-42, 1991.
Grossweiner, Photochemistry and photobiology 46(5):911-917, 1987.
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.
Hillemans, International Journal of Cancer, 81(1):34—8, 1999.
D.J. Hnatowich et al.,Radioactive Labeling of Antibody: A Simple and Efficient Method, Science, vol. 220, 1983, 613-615.
PCT,Internaional Searh Report, PCT/US02/19185, Mailed on Jan. 23, 2003 (3 pages).
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,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 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.
G. Jori,Novel Therapeutic Modalities Based on Photosensitized Processes, Journal of Photochemistry and Photobiology B: Biology, No. 60, 1997, 12-18.
M. Korbelik,Photosensitizers in photodynamic therapy, Periodicum Biologorum, vol. 93, No. 4, 1991, 563-574.
Li, Journal of Photochemistry and photobiology, B: Biology, 60 (2-3):79-86, 2001.
K. Licha et al.,New contrast agents for optical imaging: acid-cleavable conjugates of cyanine dyes with biomedicals, In Biomedical Imaging: Reporters, Dyes, and Instrumentation, D.J. Bornhop, C. Contag, and E.M. Servick-Muraca (Eds.), 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 hyporcrellin 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. Parassi 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.
Pasto et al.,Photolysis of Alkyl 4-Nitrobenzenesulfenates. A New and Versatile Method for the Generation of Free Radicals, J. Org. Chem. 1990, 55:5815-5816.
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.
Petrovic et al.,Free Radical Phenylthio Group Transfer to Nonactivated g-Carbon Atom in the Photolysis Reactions of Alkyl Benzenesulfenates, Tetrahedron Letters 38:7107-7110, 1997.
Phillips,Chemical Mechanisms in Photodynamic Therapy with Phthalocyanines, Prog. Reaction Kinetics, 22:175-300, 1997.
Pope, Journal of Urology, 145(5):1064-1070, 1991.
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.
P.J. van Geel et al.,Photosensitizing Efficacy of MTHPC-PDT Compared to Photofrin-PDT in the RIFI Mouse Tumour and Normal Skin, Int. J. Cancer, vol. 60, 1995, 388-394.
Vaupel, Strahlentherapie und Onkologie: Organ der Deutcshen Rontgengesellschaft, 174(Supp 4):6-12, 1998.
Written Opinion issued regarding International Application No. PCT/US02/19185 (Jun. 4, 2003) (5 pgs).
International Preliminary Examination Reportissued regarding PCT/US02/19185 (Oct. 8, 2003) (5 pgs).
Ferreira, Paula M.T. et al.,Synthesis of non-proteinogenic amino acids from N-(4-toluenesulfonyl)dehydroalanine derivatives, Peptides 2002, pp. 94-95 (2 pgs).
Ferreira, Paula M.T. et al.,Synthesis of Non-Natural Amino Acids from N-(p-Tolylsulfonyl)-α,β-didehydroamino Acid Derivatives, Eur. J. Org. Chem., pp. 2635-2644 (2002) (10 pgs).
Ruano, Jose L. Garcia;A General and Expeditious One-Pot Synthesis of Sulfoxides in High Optical Purity from Nonephedrine-Derived Sulfamidites; 2003 American Chemical Society Dec. 14, 2002 (4 pgs).
Ferreira, Paula M., et al;Synthesis of non-proteinogenic amino acids from N-(4-toluenesulfonyl)dehydroamino acid derivaties; Tetrahedron Letters 43 (2002) 4495-4497 (3 pgs).
Rosen, Oren, et al;Thiolysis of the 3-nitro-2pyridinesulfenyl(Npys)protecting group; Int. J. Peptide Protein Res. 35, 1990, 545-549 (5 pgs).
Rosen, O. et al;3-Nitro-2-Pyridinesulfenyul(Npys): A Versatile Protecting Group in Peptide SynthesisDepartment of Organic Chemistry, The Weizmann Institute of Science Rehovot 76100, Israel, Peptides 1988 (3 pgs).
Matsueda, Rei, et al;3-Nitro-2-Pyri
Achilefu Samuel I.
Bugaj Joseph E.
Cantrell Gary L.
Dorshow Richard B.
Rajagopalan Raghavan
Lukton David
Mallinckrodt Inc.
Thompson Hine LLP
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