In vitro cell culture in media containing beta-alanyl-taurine or

Chemistry: molecular biology and microbiology – Animal cell – per se ; composition thereof; process of...

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435384, 435404, 435405, 435410, 435420, 4354301, 435245, C12N 500, C12N 502, C12N 504, C12N 506

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active

060965363

ABSTRACT:
Compounds termed "vitaletheine modulators" which include beta-alanyl-taurine and carbobenzoxy beta-alanyl-taurine are synthesized and added to culture media for in vitro culture of cells such as mammalian or plant cells. The compounds support cell vitality, and provide increased cellular life span, increased cellular bioproductivity, improved cellular function, and adaption of resistant cells to culturing. Carbobenzoxy beta-alanyl-taurine is produced by coupling .beta.-alanine, which has it's terminal amine protected with a carbobenzoxy (CBZ) group, to N-hydroxysuccinimide to produce an active ester of .beta.-alanine, coupling two of the active esters to cystamine to produce a CBZ-protected .beta.-alethine having an internal disulfide bond, isolating and purifying the CBZ-protected .beta.-alethine, and reacting the CBZ-protected .beta.-alethine with iodine to oxidize the disulfide bond to obtain carbobenzoxy beta-alanyl-taurine. Beta-alanyl-taurine is produced by the same procedure except that after oxidizing with iodine, the carbobenzoxy beta-alanyl-taurine is irradiated with UV radiation to remove the CBZ-protecting group.

REFERENCES:
patent: 2722551 (1955-11-01), Snell
patent: 3876799 (1975-04-01), Tamura et al.
patent: 4060551 (1977-11-01), Uchikuga et al.
patent: 4102948 (1978-07-01), Feuer et al.
patent: 4218404 (1980-08-01), Feuer et al.
patent: 4552765 (1985-11-01), Mita et al.
patent: 4571430 (1986-02-01), Byrne
patent: 5370868 (1994-12-01), Knight et al.
patent: 5578313 (1996-11-01), Knight et al.
Weisman et al, "Tricyclic Orthoacetamides and Orthopropionamides: Conformational Analysis and Sterochemical Effects upon .sup.13 C NMR Spectra", Tetrahdron Letters 22(44):4365-4368 (1981).
Sokolvsky et al, "On the Synthesis of Cystein Peptides", J. Am. Chem. Soc. 86:1202-1206 (1967).
Fifth Report by T. Pantev, "Synthesis of S-(omega-Carboxamidinoalkyl-)-Isothiocarbamides", Nauchnoizskd. Inst. Radiobiol. Radiats. Knigy. 5:57-62 (1975).
Merck Index, #221 (1974).
Garfinkel, "Is Aging Inevitable? The Intracellular Zinc Deficiency Hypothesis of Aging", Med-Hypothesis 19(2):117-37 (1986).
Meister & Anderson, Glutathione, pp. 743-760 (1985).
Chen et al, "The Role of Cholesterol in Malignancy", Prog. exp. Tumor Res. 22:275-316 (1978).
Gilbert, "Molecular and Cellular Aspects of Thiol-Disulfide Exchange", Adv. Enzymol. Metab. Rel. Area 63:69-172 (1990).
Ziegler, "Role of Reversible Oxidation-Reduction of Enzyme Thiols-Disulfides in Metabolic Regulation", Ann. Biochem. 54:305-329 (1985).
Chopra, "Sulfhydryl Groups and the Monodeiodination of Thyroxine to Triiodothyronine", Science 199:904-905 (1978).
Kawachi et al, "Solubilization and Purification of .beta.-Hydroxy-.beta.-methylglutaryl Coenzyme A Reductase from Rat Liver", Biochemistry 9:1700-1705 (1970).
Dotan et al, "Thiol-Disulfide-Dependent Interconversion of Active and Latent Forms of Rat Hepatic 3-Hydroxy-3-Methylglutaryl-Coenzyme A Reductase", Biochemica et Biophysica Acta. 713:427-434 (1982).
Sabine, Chapter 1, "General Distribution and Importance of HMGCoA Reductase", pp. 3-18 (1980).
Rodwell et al, "Regulation of Hepatic 3-Hydroxy-3-Methylglutaryl-Coenzyme A Reductase", Adv. Enzymol. 38:373-412 (1973).
DeFlora et al, "Antioxidant Activity and Other Mechanisms of Thiols Involved in Chemoprevention of Mutation and Cancer", The American Journal of Medicine 91:3C-122S (1991).
Roederer et al, "Cytokine-stimulated human immunodeficiency virus replication is inhibited by N-acetyl-L-cysteine", Proc. Natl. Acad. Sci. USA 87:4884-4888 (1990).
Tsao et al, "Glutathione and glutathione S-transferases in clones of cultured rat liver epithelial cells that express varying activity of gamma-glutamyl transpeptidase", Mol. Carcinol. 2(3):144-9 (1989).
Droge et al, "Modulation of Lymphocyte Functions and Immune Responses by Cysteine and Cysteine Derivatives", The American Journal of Medicine 91:3C-140S (1991).
Eck et al, "Elevated plasma glutamate concentrations in HIV-1-infected patients may contribute to loss of macrophage and lymphocyte functions", Int. Immunol. 1(4):367-72 (1989).
Frankova, "The Effects Of Amino Acids with Sulfhydryl Groups On Herpes viruses in Vitro", . . . eta virol. 11:559-561, (1967).
Kalebic et al, "Suppression of human immunodeficiency virus expression in chronically infected monocytic cells by glutathione, glutathione ester, and N-acetylcysteine", Proc. Natl. Acad. Sci. USA 88:986-990 (1991).
Eck et al, "Low Concentrations of Acid-Soluble Thiol (Cysteine) in the Blood Plasma of HIV-1-Infected Patients", Biol. Chem. Hoppe Segler 370:101-8 (1989).
Buhl et al, "Systemic Glutathione Deficiency in Symptom-Free HIV-Seropositive Individuals", The Lancet 1294-1297 (1989).
Guder et al, "The Influence of Thyroid Hormones on .beta.-Hydroxy-.beta.-Methylglutaryl-Coenzyme A Reductase of Rat Liver", European J. Biochem. 4:273-278 (1968).
Magee, "Post-translational process of ras proteins", Biochem. Soc. Trans. 19(5):875-6 (1989).
Schafer et al, "Genetic and Pharmacological Suppression of Oncogenic Mutations in RAS Genes of Yeast and Humans", Research Articles, pp. 379-385 (1989).
Gregg et al, "3-Hydroxy-3-Methylglutaryl Coenzyme A Reductase and Cancer", Cholesterol and Cancer, Chapter 17, pp. 245-257 (19--).
Paukovits et al, "Protection From Arabinofuranosylcytosine and n-Mustart-Induced Myelotoxicity Using Hemoregulatory Peptide pGlu-Glu-Asp-Cys-Lys Monomer and Dimer", Blood 77(6):1313-1319 (1991).
Laerum et al, "The Dimer of Hemoregulatory Peptide (HP5B) Stimulates Mouse and Human Myelopoiesis in vitro", Exp. Hematol. 16:274-280 (1988).
Amery et al, "Levamisole and Immunotherapy: Some Theoretic and Practical Considerations and Their Relevance to Human Disease", Oncology 38:168-181 (1981).
Anderson et al, "The Use of Esters of N-Hydroxysuccinimide in Peptide Synthesis", J. Am. Chem. Soc. 86:1839-42 (1964).
Garcia-Penarrubia et al, "Antibacterial Activity of Human Natural Killer Cells", J. Exp. Med. 169:99-113 (1989).
Dessypris et al, "Increased Sensitivity to Complement of Erythroid and Myeloid Progenitors in Paroxysmal Nocturnal Hemoglobinuria", The New England Journal of Medicine 309(12):690-693 (1983).
Suthanthiran et al, Glutathione rgulates activation-dep. DNA syn. in highly purified normal human T lymphocites stimulated via the CD2 and CD3 antigens, Proc. Natl. Acad. Sci. 87:3343 (1990).
Yudkoff et al, "Cysteamine Therapy in Cystinosis", New England J. Med. 304:141 (1981).
Zhang et al, "A Major Inducer of Anticarcinogenic Protective Enzymes from Broccoli: Isolation and Elucidation of Structure" 89:2399 (1992).
Goetz et al, "Clinical Management of Progressive Multifocal Benign and Malignant Melanomas of Horses with Oral Cimetidine".
Amitage et al, The Lancet, Apr. 21, 1979, "Antitumor Effect of Cimetidine".
Thorne, Lynch, Sheehan, "Cimetidine and Coumarin Therapy of Melanoma", The Lancet, Aug. 7, 1982, p. 328.
Osband et al, "Successful Tumour Immunotherapy with Cimetidine in Mice", The Lancet, Mar. 21, 1981, p. 636.
Flodgren et al, "Metastatic Malignant Melanoma: Regression Induced by Combined Treatment with Interferon [HulFN-.alpha.(Le)] and Cimetidine", Br. J. Cancer 32:657 (1983).
Hill et al, Interferon and Cimetidine for Malignant Melanoma, New England J. Med., Feb. 3, 1982, p. 286.
Somogyi et al, "Cimetidine Reduces Procainamide Elimination", N. Engl. J. Med. 307:1080, Oct. 21.
Currie, "Effect of Autoimmunization with Irradicated Tumor Cells on Specific Cell-Mediated Immunity in Patients with Malignant Melanoma", Proc. Rory. Soc. Med. 65:144 (1972).
Oiry et al, "Synthesis and Radioprotective Activity of New Cysteamine and Cystamine Derivatives", J. Med. Chem. 29(11):2217-2225 (1989).

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