Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-11-20
2000-10-17
Owens, Amelia
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D49300
Patent
active
06133460&
ABSTRACT:
Psoralen compound compositions are synthesized which have primaryamino substitutions on the 3-, 4-, 5-, and 8- positions of the psoralen, which yet permit their binding to nucleic acid of pathogens. Reaction conditions that photoactivate these psoralens result in the inactivation of pathogens which contain nucleic acid. The compounds show similar activity in test systems to 4' and 5' derivatives of psoralen useful for inactivation of pathogens in blood products. In addition to the psoralen compositions, the invention contemplates such inactivating methods using the new psoralens.
REFERENCES:
patent: 4124598 (1978-11-01), Hearst et al.
patent: 4169204 (1979-09-01), Hearst et al.
patent: 4196281 (1980-04-01), Hearst et al.
patent: 4216154 (1980-08-01), Kaufman
patent: 4235781 (1980-11-01), Kaufman
patent: 4269851 (1981-05-01), Kaufman
patent: 4269852 (1981-05-01), Kaufman
patent: 4279922 (1981-07-01), Kaufman
patent: 4292822 (1981-10-01), Kaufman
patent: 4294847 (1981-10-01), Kaufman
patent: 4298614 (1981-11-01), Kaufman
patent: 4321919 (1982-03-01), Edelson
patent: 4328239 (1982-05-01), Kaufman
patent: 4370344 (1983-01-01), Kaufman
patent: 4545987 (1985-10-01), Giles et al.
patent: 4599303 (1986-07-01), Yabusaki et al.
patent: 4613322 (1986-09-01), Edelson
patent: 4684521 (1987-08-01), Edelson
patent: 4693981 (1987-09-01), Wiesehahn et al.
patent: 4727027 (1988-02-01), Wiesehahn et al.
patent: 4737454 (1988-04-01), Dattagupta et al.
patent: 4748120 (1988-05-01), Wiesehahn
patent: 4878891 (1989-11-01), Judy et al.
patent: 4960408 (1990-10-01), Klainer et al.
patent: 5030200 (1991-07-01), Judy et al.
patent: 5106619 (1992-04-01), Wiesehahn et al.
patent: 5120649 (1992-06-01), Horowitz et al.
patent: 5288605 (1994-02-01), Lin et al.
patent: 5354774 (1994-10-01), Deckelbaum et al.
patent: 5418130 (1995-05-01), Platz et al.
patent: 5440052 (1995-08-01), Makriyannis et al.
patent: 5473083 (1995-12-01), Heindel et al.
patent: 5482828 (1996-01-01), Lin et al.
patent: 5516629 (1996-05-01), Park et al.
patent: 5532146 (1996-07-01), Cimino et al.
patent: 5556993 (1996-09-01), Wollowitz et al.
patent: 5571666 (1996-11-01), Floyd et al.
patent: 5578736 (1996-11-01), Wollowitz et al.
patent: 5593823 (1997-01-01), Wollowitz et al.
patent: 5654443 (1997-08-01), Wollowitz et al.
patent: 5683661 (1997-11-01), Hearst et al.
patent: 5709991 (1998-01-01), Lin et al.
patent: 5827640 (1998-10-01), Wiggins et al.
patent: 5827741 (1998-10-01), Beattie et al.
"How Safe Is Our Blood", U.S. News and World Report, 68-78 (1994).
Adams, et al., "The Pechmann Reaction," Organic Reactions vol. VII Chapter 1, Wiley, NY (1953).
Alter et al. "Photochemical Decontamination of Blood Components Containing Hepatitis B and Non-A, Non-B Virus," The Lancet (ii:1446-1450) (1988).
Alter H., "A reassessment of the literature on the hepatitis G virus" Transfusion 37:569-572 (1997).
Ben-Hur & Horowitz "Advances in photochemical approaches for blood sterlization" Photochem. & Photobio. 62:3 383-388 (1995).
Bender D. et al., "Psoralen synthesis improvements in furano ring formation application to the synthesis of 4,5'8-trimethylpsoralen," J. Org. Chem. 44:13 2176-2180 (1979).
Bertolini, F., et al., "Platelet Quality After 15-day Storage of Platelet Concentrates Prepared from Buffy Coats and Stored in a Glucose-Free Crystalloid Medium," Transfusion 32:9-16 (1992).
Blajchman, M.A., Blood Safety: Current Challenges, S.J. Nance ed. "Bacteria in the blood supply: An overlooked issue in transfusion medicine" pp. 213-228 (1992).
Bowden, R.A. Blood Safety: Current Challenges, S.J. Nance ed "Cytomegalovirus: Transmission by Blood Components and Measures of Prevention" pp.201-211 (1992).
Charalambous et al. "5'-Azido-.increment.8-THC: A novel photoaffinity label for the cannabinoid receptor" Med. Chem. 35:3076-3079 (1992).
Chiu, E. et al., "A prospective study of symptomatic bacteremia following platelet transfusion and of its management" Transfusion 34:950-954 (1994).
Cimino et al. "Psoralens as Photoactive Probes of Nucleic Acid Structure and Function: Organic Chemistry, Photochemistry, and Biochemistry," Ann. Rev. Biochem. 54:1151-1193 (1985).
Cotten M. et al., "Psoralen treatment of adenovirus particles eliminates virus replication and transcription while maintaining the endosomolytic activity of the virus capsid," Virology 205:254-261 (1994).
Crombie, L. et al. "Synthesis of the Mammea Coumarins Part 2. Experiments in the Mammea E series and synthesis of Mammea E/AC" J. Chem. Soc. Perk. Trans. I 333-343 (1987).
Dodd et al. "Inactivation of viruses in platelet suspensions that retain their in vitro characteristics: comparison of psoralen-ultraviolet A and merocyanine 540 visible light methods," Transfusion 31:483-490 (1991).
Dodd, Blood Supply: Risks, Perceptions, and Prospects for the Future S.J. Nance ed. p1 (1994).
Dodd, R. Y. "Will blood products be free of infectious agents?" Nance S.J. ed. Transfusion Med. in the 1990's AABB (1990).
Elix et al., "Synthetic confirmation of the structure of the lichen benzyl esters alectorialic and barbatolic acids" Aust. J. Chem. 40:1841-50 (1987).
Elsner and Mouritsen "Use of psoralens for covalent immobilization of biomolecules in solid phase assays" Bioconjugate Chem. 5(5):463-467 (1994).
Fall et al. "A convenient synthesis of benzofuran-3-acetic acids" Heterocycles 41:647-650 (1995).
Friedman L and Stromberg R. "Viral inactivation and reduction in cellular blood products," Rev. Fr. Transfus. Hemobiol. 36:83-91 (1993).
Gasparro et al., "Receptor-mediated photo-cytotoxicity: synthesis of a photoactivatable psoralen derivative conjugated to insulin" Biochem. and Bioiphys. Res. Comm. 141(2):502-509 (1986).
Goldenberg et al. "Synthesis and Properties of Novel Psoralen Derivatives," Biochemistry 27:6971-6976 (1988).
Groene S. and Shaw D. :Psoralen preparation of antigenically intact noninfectious rotavirus particles, J. Virol. Methods 38 93-102 (1992).
Gupta et al., "Synthesis of organomagnesium .beta.-diketonates and alkoxides" J. Organomet. Chem 452:1-4 (1993).
Hansen J. et al. "Psoralenamines. 3..sup.1 Synthesis, pharmacological behavior, and DNA binding of 5-(aminomethyl)-8methoxy-,5-[[(3-aminopropyl)oxy]methyl]-, and 8-[(3-aminopropyl)oxy]psoralen derivatives" J. Med. Chem. 28:1001-1010 (1985).
Hanson, C.V. "Photochemical Inactivation of Viruses with Psorlens: An Overview," Blood Cells: 18:7-25 (1992).
Hearst et al. "The Reaction of the Psoralens with Deoxyribonucleic Acid," Quart. Rev. Biophys. 17:1-44 (1984).
Hearst, J.E., and Thiry, L., "The photoinactivation of an RNA animal virus, vesicular stomatitis virus, with the aid of newly synthesized psoralen derivatives," Nucleic Acids Research, 4:1339-1347 (1977).
Heinmets, et al., "Inactivation of viruses in plasma by photosensitized oxidation." Walter Reed Research Report WRAIR 53-55. (1955) pp. 1-16.
Hilfenhaus, J., et al., "A strategy for testing established human plasma protein manufacturing procedures for their ability to inactivate or eliminate human immunodeficiency virus," J. Biol. Std. 15:251-263 (1987).
Horowitz, B., et al., "Inactivation of viruses in labile blood derivatives," Transfusion 25:516-522 (1985).
Hyde and Hearst, "Binding of Psoralen Derivatives to DNA and Chromatin: Influence of the Ionic Environment on Dark Binding and Photoreactivity," Biochemistry 17:1251-1252 (1978).
Isaacs et al. A Photochemical Characterization of Reactions of Psoralen Derivatives with DNA, Trends in Photobiology (Plenum) pp. 279-294 (1982).
Isaacs et al. "In Vitro Characterization of the Reaction of Four Psoralen Derivatives with DNA," NCI Monograph 66:21-30 (1984).
Isaacs et al. "Synthesis and Characterization of New Psoralen Derivatives with Superior Photoreactivity with DNA and RNA," Biochemistry 16:1058-1064 (1977).
Kaufman K. et al., "Reactions of furocoumarins II(1). Synthetic aminomethyl psoralens via chloromethylationor benzylic bromination," J. Heterocyclic Chem. 19 1051-1056 (1982).
Lackritz E., et al. "Estimated risk of transmission of HIV by screened blood in the United States," New Eng. J. Med. 333:1721 (1995).
Lambert et al., "Ap
Nerio Aileen
Wollowitz Susan
Cerus Corporation
Owens Amelia
Tessman John W.
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