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(12) United States Patent (10) Patent No.: US 6, 177,059 B1 Matsuda Et Al

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(12) United States Patent (10) Patent No.: US 6, 177,059 B1 Matsuda Et Al USOO6177059B1 (12) United States Patent (10) Patent No.: US 6, 177,059 B1 Matsuda et al. (45) Date of Patent: Jan. 23, 2001 (54) GPIB-LIPID COMPLEX AND USES (56) References Cited THEREOF U.S. PATENT DOCUMENTS (75) Inventors: Hiroshi Matsuda, Osaka; Kaeko 3,927,047 12/1975 Ichikawa et al. ...................... 554/63 Kamide, Yasuo Amatsuji, both of 5,399,331 * 3/1995 Loughrey et al. .. 424/450 Hirakata; Takashi Imagawa, Fukuoka; 5,428,008 6/1995 Chao et al. .............................. 514/8 Yasuo Ikeda, Tokyo; Mitsuru Murata, FOREIGN PATENT DOCUMENTS Niiza, all of (JP) 4-506518 * 11/1992 (JP). (73) Assignee: Yoshitomi Pharmaceutical Industries, Ltd., Osaka (JP) OTHER PUBLICATIONS Muszbek et al. Glycoprotein Ib and Glycoprotein IX in (*) Notice: Under 35 U.S.C. 154(b), the term of this Human Platelets . J. Biol. Chem. Vol. 264, No. 17, pp. patent shall be extended for 0 days. 9716-9719, Jun. 15, 1989.* Sie et al. Reconstitution of Liposomes Bearing Platelet (21) Appl. No.: 09/117,746 Membrane . Protides Biol. Fluids, Volume Date 1981, (22) PCT Filed: Feb. 6, 1997 29th, pp. 79-83, 1982.* (86) PCT No.: PCT/JP97/00284 * cited by examiner Primary Examiner Jeffrey E. Russel S371 Date: Dec. 3, 1998 (74) Attorney, Agent, or Firm-Sughrue, Mion, Zinn, S 102(e) Date: Dec. 3, 1998 Macpeak & Seas, PLLC (87) PCT Pub. No.: WO97/29128 (57) ABSTRACT PCT Pub. Date: Aug. 14, 1997 A complex comprising a lipid and a conjugate of GPIb and lipid having a functional group, and use thereof. The GPIb (30) Foreign Application Priority Data lipid complex of the present invention is extremely useful as Feb. 7, 1996 (JP) ..................................................... 8-21482 a platelet Substitute, a pharmaceutical agent for the prophy laxis and treatment of angiopathy, vascular damages and (51) Int. Cl. .......................... A61K 9/127; A61K 38/17; thrombosis, a diagnostic for vWF deficiency and the like, a A61K 38/36; A61K 51/08; CO7K 14/705 biological or medical reagent, a reagent for Screening plate (52) U.S. Cl. .................... 424/1.21; 424/9.321; 424/9.34; let aggregation Suppressant or antithrombosis, and the like. 424/9.37; 424/9.51; 424/9.6; 424/4.5; 514/7; The GPIb-lipid complex of the present invention is also 514/8; 514/21; 530/352; 530/359; 530/381; useful as a diagnostic for finding the location of vascular 530/395; 530/410 lesion or thrombus formation, or a therapeutic agent (58) Field of Search ................................ 424/1.21, 9.321, therefor, Since it accumulates at vascular lesions. 424/9.34, 9.51, 9.6, 450; 514/5, 6, 7, 8, 21; 530/352,359, 381, 395,410 27 Claims, No Drawings US 6,177,059 B1 1 2 GPB-LPID COMPLEX AND USES (9) A pharmaceutical agent for examination or diagnosis, THEREOF which comprises, as an active ingredient, a labeling Substance and a complex comprising a lipid and a con TECHNICAL FIELD jugate of GPIb and a lipid having a functional group. 5 (10) The pharmaceutical agent of above (9), wherein the The present invention relates to a GPIb-lipid complex and labeling Substance is a radioisotope, paramagnetic metal use thereof. More particularly, the present invention relates for MRI, iodide compound for X ray imaging, fluorescent to a GPIb-lipid complex that can be effectively used for the Substance or pigment. examination, diagnosis and treatment of vascular lesions and (11) A drug-containing composition comprising, as an active to use thereof. ingredient, a drug and a complex comprising a lipid and a conjugate of GPIb and a lipid having a functional group. BACKGROUND ART (12) The composition of above (11), wherein the drug is a Various glycoproteins (GP) are present on the Surface of hemostatic agent, vasoconstrictor, antiinflammatory platelet membrane, and are involved in the expression of agent, fibrinolytic agent, anti-blood coagulator or anti platelet functions. GPIb is one of the platelet membrane platelet agent. glycoproteins, and functions as a receptor of Von Willebrand 15 (13) A conjugate of GPIb and a lipid having a functional factor (vWF). GPIb is a heterodimer having a molecular grOup. weight of 160,000, wherein C. chain and B chain form a (14) The conjugate of above (13), wherein the GPIb is a disulfide bond. GPIb itself, GPIb C. chain or GPIb C. chain fragment. (15) The conjugate of above (13), wherein the GPIb is an When Vascular damages are caused, platelets quickly analog, mutant, modified compound, derivative or Sugar adhere to the lesion and form platelet thrombus by aggre chain adduct, having a von Willebrand factor-binding gation and the like. In forming the platelet thrombus, VWF capability that is almost at the same level as GPIb. plays an important role as an adhesive protein. It is consid (16) The conjugate of above (13), wherein the GPIb is ered that GPIb binds with VWF as a receptor thereof and defective in a transmembrane Site. activates or promotes adhesion and aggregation of platelets (17) The conjugate of above (13), wherein the lipid having via v WF at said vascular lesion. In addition, the binding of 25 a functional group is a phospholipid, glycolipid, fatty vWF and GPIb functions to stop bleeding at the vascular acid, glyceride, cholesterol or amphipathic lipid. lesion but also forms pathologic thrombus. Thus, GPIb is (18) The conjugate of above (13), wherein the functional expected to be effectively used for the examination and group is an amino, carboxyl, thiol or aldehyde. diagnosis of vascular lesion, detection of pathologic (19) The conjugate of above (13), wherein the GPIb and the thrombus, and treatment thereof. lipid having a functional group are chemically bonded by a crosslinking agent. Nevertheless, the use of isolated GPIb has not proved (20) The conjugate of above (13), wherein the molar ratio of Successful in artificial expression of the physiological activ the GPIb:lipid having a functional group is 1:1-1:20. ity as mentioned above. In other words, Some idea in the (21) The complex of above (1), wherein the complex of a aspect of formulation of pharmaceutical preparations is 35 lipid and a conjugate of GPIb and a lipid having a needed to practically use GPIb as a pharmaceutical agent or functional group is prepared after preparing Said conju reagent. gate. The present invention is described in more detail in the DISCLOSURE OF THE INVENTION following. (I) Conjugate of GPIb and lipid having functional Under the circumstances, the present inventors have made 40 group (GPIb conjugate) intensive Studies and first found that the physiological CD GPIb activity can be expressed by preparing a lipid complex The GPIb to be used in the present invention may be GPIb comprising a conjugate of GPIb and a certain lipid and a itself, its C. chain, VWF binding region, namely, a GPIb normal lipid, which resulted in the completion of the present fragment such as GPIb C. chain His(1)-Thr(302) fragment invention. 45 and the like. An analog, a modified compound, a mutant, a Accordingly, the present invention provides the follow derivative and a Sugar chain adduct thereof are encompassed Ing. in the Scope of the present invention, as long as they have (1) A complex comprising a lipid and a conjugate of GPIb almost the same level of VWF binding capability as GPIb. and a lipid having a functional group. Moreover, they may lack a transmembrane Site. In the (2) The complex of above (1), which is in the form of a 50 present invention, those without this transmembrane Site are liposome. preferably used. (3) The complex of above (1), wherein the lipid is a Specific examples thereof include GPIb-related Sub phospholipid, glycolipid, cholesterol, fatty acid or deriva stances disclosed in WO92/ 16225, WO93/ 13784, WO93/ tive thereof. 16712, Japanese Patent Unexamined Publication No. (4) The complex of above (1), wherein the molar ratio of the 55 100196/1989, Japanese Patent Unexamined Publication No. GPIb:lipid is 1:10–1:1000. 221394/1989 and Japanese Patent Application under PCT (5) The complex of above (1), wherein the complex can laid-open under kohyo No. 503708/1993. aggregate in the presence of ristocetin. Examples thereof include GPIb, GPIb C. chain, GPIb C. (6) A pharmaceutical composition comprising a complex chain fragment, His(1)-Ala(302), His(1)-Arg(293), Ala comprising a lipid and a conjugate of GPIb and a lipid 60 (165)-Leu (184), Gln(180)-Phe(199), His(195)-Leu(214), having a functional group. ASn(210)-Val(229), Glu(225)-Ala(244), Thr(240)-Tyr(259), (7) The pharmaceutical composition of above (6), wherein ASn(61)-Thr(75), Gln(71)-Ser(85), Thr(81)-Leu(95), Gln the composition is a platelet Substitute. (97)-Arg(111), Leu(136)-Leu(150), ASn(210)-Ala(224), Gln (8) The pharmaceutical composition of above (6), wherein (221)-Asp(235) and Ser(241)-Asp(255). the composition is an agent for the prophylaxis and 65 A substituted compound is exemplified by GPIb C. chain treatment of vascular disorders, vascular damages or fragments consisting of His(1)-Ala(302), wherein Gly(233) thrombosis. and Met(239) are respectively substituted by Val. US 6,177,059 B1 3 4 The GPIb can be prepared by any method and a method group of GPIb are bonded via arbodiimide, a method comprising extraction and isolation from platelet membrane, wherein sugar chain of GPIb is oxidized to give aldehyde a method using cell culture and a production method using group which is bonded to form Schiffbase with amine of PE, genetic engineering are exemplified. a method wherein SH group of GPIb and phospholipid (2) Lipid having functional group having a terminal SH group (e.g., 1,2-dioleoyl-sn-glycero With regard to the lipids having a functional group, a 3-phosphatidylthioethanol and the like) form a disulfide functional group capable of directly or indirectly forming a bond under oxidation conditions, a method wherein gly bond with GPIb is exemplified by amino group (NH), colipid is oxidized to give aldehyde group which is bonded carboxyl group (COOH), thiol group (SH), aldehyde group to amino of GPIb, a method wherein fatty acid is bonded to (CHO) and the like.
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