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(12) United States Patent (10) Patent No.: US 6,274,565 B1 Katsumi (45) Date of Patent: Aug

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(12) United States Patent (10) Patent No.: US 6,274,565 B1 Katsumi (45) Date of Patent: Aug USOO6274565B1 (12) United States Patent (10) Patent No.: US 6,274,565 B1 Katsumi (45) Date of Patent: Aug. 14, 2001 (54) INHIBITOR OF ACTIVATION OF B-GLUCAN Ashida, Insect Biochem. vol. 11, pp. 57-61, 63-65, 1981. RECOGNITION PROTEIN (Discussed in the Specification). Ochiai et al., The Journal of Biological Chemistry, vol. 263, (75) Inventor: Yoichi Katsumi, Hyougo (JP) No. 24, pp. 12056–12062, 1988. (Discussed in the Specifi (73) Assignee: Wako Pure Chemical Industries, Ltd., cation). Osaka (JP) Tsuchiya, FEMS Immunology and Medical Microbiology, 15, pp. 129-134, 1996. (Discussed in the Specification). (*) Notice: Subject to any disclaimer, the term of this First Department of Biochemistry, School of Medicine, patent is extended or adjusted under 35 Showa University; XP-002063489, Chapter 25; Diverse U.S.C. 154(b) by 0 days. Biological Activity of PSK (Krestin), A Protein-Bound Polysaccharide From Coriolus Versicolor (FR.) Quel.; (21) Appl. No.: 09/211,043 Hiroshi Sakegami et al. (22) Filed: Dec. 15, 1998 Institute of Biochemistry and Biotechnology, Technical Uni versity of Braunschweig, Carbohydrate Polymers 24 (1994) (30) Foreign Application Priority Data 193-197; Acetylation of a B-1, 6-branched B-1, 3-glucan, Dec. 16, 1997 (JP) ................................................... 9-363960 yielding Schizophyllan-acetate; Andre Albrecht, Udo Rau. (51) Int. Cl." ........................ A01N 43/04; A61K 31/715; A61K 35/64 * cited by examiner (52) U.S. Cl. ......................... 514/54; 424/538; 424/193.1; 536/55.1; 536/123.1; 536/123.12; 536/124; Primary Examiner James O. Wilson 435/4; 435/18; 435/19, 435/23; 435/25; (74) Attorney, Agent, or Firm-Armstrong, Westerman, 435/201; 435/206; 435/207; 435/208 Hattori, McLeland & Naughton LLP (58) Field of Search ................................ 435/4, 201, 205, (57) ABSTRACT 435/206, 207, 208; 514/54; 536/55.1, 123.1, 124, 123.12; 424/193.1, 538 The present invention relates to an inhibitor of an activation of B-glucan recognition protein in a body fluid of an insect (56) References Cited comprising a Sugar compound comprising plural member of Sugar residues, at least one of which have a Substituent at the U.S. PATENT DOCUMENTS 6-position, the Sugar residues being bonded mainly through 4,970,152 11/1990 Ashida et al. ......................... 435/19 B 1->3 linkage with one another, a proceSS for inhibiting the activation; an agent for treating the body fluid of an insect, FOREIGN PATENT DOCUMENTS a proceSS for the treatment, a novel agent for measuring O 270 039 6/1988 (EP). peptidoglycan Simply and effectively, and a process for the O 330 991 9/1989 (EP). measurement. 0.333 187 9/1989 (EP). O 397 880 11/1990 (EP). The present invention is markedly effective in that a reagent, WO 83/02123 6/1983 (WO). which are obtained form a body fluid of an insect, can easily OTHER PUBLICATIONS be obtained. Yoshida et al., Biochemical and Biophysical Research Com munication, vol. 141, No. 3, pp. 1177-1184, Dec. 30, 1986. (Discussed in the Specification). 13 Claims, 2 Drawing Sheets U.S. Patent Aug. 14, 2001 Sheet 1 of 2 US 6,274,565 B1 10000 O A O O A C KX O O an V Us O sy U Av UD O Ug 1000 O NO R He l f) 24 O 100 yms vm vm v V O O O O O O C CS v O O O O O O v O O C O vm O O qm B G CONCENTRATION (ug/ml) U.S. Patent Aug. 14, 2001 Sheet 2 of 2 US 6,274,565 B1 10000 1000 100 v yo O s s O ve S B G CONCENTRATION (ug/ml) US 6,274,565 B1 1 2 INHIBITOR OF ACTIVATION OF B-GLUCAN Yoshida, H., Ochiai, M., and Ashida, M. (1986) Biochem. RECOGNITION PROTEIN Biophys. Res. Commun. 141, 1177-1184). So, in the process mentioned above, it is necessary to remove B GRP from the BACKGROUND OF THE INVENTION body fluid of an insect before making it into the reagent to The present invention relates to an inhibitor of an acti measure the PG Specifically by affinity chromatography or Vation of 3-glucan recognition protein in a body fluid of an the like, and this removing proceSS is complicated and insect, a proceSS for inhibiting the activation; an agent for troublesome. treating a body fluid of an insect, a proceSS for the treatment; a novel agent for measuring peptidoglycan, and a proceSS for SUMMARY OF THE INVENTION the measurement. The present invention has been made in View of Such prior Peptidoglycans (hereinafter abbreviated as PG) are gly state of the art as above and the object thereof is to provide coprotein containing N-acetylmuramic acid residue or a novel inhibitor of an activation of BGRP in the body fluid N-glycolylmuramic acid residue and D-amino acid residues, of an insect, a process for inhibiting the activation by the use and they play, as bacterial cell wall components, an impor of Said inhibitor, an agent for treating a body fluid of an tant role for retention of the form of bacteria. 15 insect, a treating proceSS using Said agent, an effective PG have various biological activities Such as various reagent for measuring PG, and a process for measuring PG, functions to immune response cells (e.g. macrophages, B more particularly. lymphocytes, T lymphocytes, etc.), destruction of blood The present invention provides an inhibitor of the acti platelets, growth enhancement of fibroblasts, enhancement vation of 3 GRP in a body fluid of an insect comprising a of bone resorption, activation of complements, enhancement Sugar compound comprising plural member of Sugar or inhibition of humoral immune responses, enhancement of residues, at least one of which have a Substituent at the cellular immunity, Stimulation of cell endotherial Systems, 6-position, the Sugar residues being bonded mainly through transient leukopenia and Subsequent hypercytosis, enhance B 1->3 linkage with one another. ment of the functions of interferon inducing factors, poten 25 The present invention also provides a process for inhib tation of natural resistance, induction of experimental iting the activation of B GRP comprising treating a body autoimmune diseases, pyrogen functions, enhancement of fluid of an insect with a Sugar compound comprising plural sensitivity to the toxicity of endotoxins (hereinafter abbre member of Sugar residues, at least one of which have a viated as ET), enhancement or inhibition of sleep, formation Substituent at the 6-position, the Sugar residues being of epithelioid granulomas, functions of hemorrhagic necro bonded mainly through B 1->3 linkage with one another. sis at Sites treated with tubercle bacillus or the like and acute The present invention further provides an agent for treat or chronic toxicity. ing a body fluid of an insect comprising a Sugar compound While ET are contained only in Gram-negative bacteria, comprising plural member of Sugar residues, at least one of PG are contained both in Gram-positive bacteria and Gram which have a Substituent at the 6-position, the Sugar residues negative bacteria. And PG are contained in the cell walls to 35 being bonded mainly through f3 1->3 linkage with one form thick layers at the outermost shells of cell walls in the another. Gram-positive bacteria, and are contained in the cell walls to form thin layers inside outer membranes of the cell walls in The present invention still further provides a process for the Gram-negative bacteria. Almost all procaryotes contain treating a body fluid of an insect comprising contacting a PG in their cell walls except for archaebacteria (e.g. methane body fluid of an insect with a Sugar compound comprising bacteria, highly acidophilic bacteria, etc.) which contain 40 plural member of Sugar residues, at least one of which have neither ET nor PG. On the other hand, PG are not contained a Substituent at the 6-position, the Sugar residues being in the cell components of eukaryotes Such as mammals and bonded mainly through B 1->3 linkage with one another. hence it is considered that bacteria are present where PG is The present invention additionally provides a reagent for measuring PG comprising a body fluid of an insect and a present. 45 Therefore, PG measurement is useful for detecting a trace Sugar compound comprising plural member of Sugar amount of microorganisms. Such as bacteria and blue-green residues, at least one of which have as a Substituent at the algae (Cyanophyceae), which contain PG as a constituent of 6-position, the Sugar residues being bonded mainly through cell wall, and is expected to be applicable to, for example, B 1->3 linkage with one another. Safety tests of drugs and the like, microbial tests of water and 50 The present invention Still additionally provides a process foods, and diagnoses of infectious diseases. for measuring PG comprising reacting a Sample with a body AS a process for measuring PG, there has been reported, fluid of an insect, in the presence of a Sugar compound for example, a method using a reagent derived from a body comprising plural member of Sugar residues, at least one of fluid of an insect (JP-B 7-114707). The body fluid of an which have a Substituent at the 6-position, the Sugar residues insect contains factors constituting the pro-phenol oxidase 55 being bonded mainly through f3 1->3 linkage with one (hereinafter abbreviated as proPO) cascade, and usually, another. they are not yet activated (inactive type factors). The body BRIEF DESCRIPTION OF THE DRAWINGS fluid of an insect contains, as one of the factors, a Substance which binds to PG to activate the proPO cascade (PG FIG.
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