JPS6023084B2 - 代用血液 - Google Patents
代用血液Info
- Publication number
- JPS6023084B2 JPS6023084B2 JP54087910A JP8791079A JPS6023084B2 JP S6023084 B2 JPS6023084 B2 JP S6023084B2 JP 54087910 A JP54087910 A JP 54087910A JP 8791079 A JP8791079 A JP 8791079A JP S6023084 B2 JPS6023084 B2 JP S6023084B2
- Authority
- JP
- Japan
- Prior art keywords
- hemoglobin
- polyethylene glycol
- mol
- moles
- molecular weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000003633 blood substitute Substances 0.000 title claims description 5
- 108010054147 Hemoglobins Proteins 0.000 claims description 43
- 102000001554 Hemoglobins Human genes 0.000 claims description 43
- 239000002202 Polyethylene glycol Substances 0.000 claims description 26
- 229920001223 polyethylene glycol Polymers 0.000 claims description 26
- 239000000126 substance Substances 0.000 claims description 9
- 229920001451 polypropylene glycol Polymers 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 239000000872 buffer Substances 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 210000004204 blood vessel Anatomy 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- -1 stearyl ester Chemical class 0.000 description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- YZBOVSFWWNVKRJ-UHFFFAOYSA-M 2-butoxycarbonylbenzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1C([O-])=O YZBOVSFWWNVKRJ-UHFFFAOYSA-M 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011403 purification operation Methods 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 1
- MUHFRORXWCGZGE-KTKRTIGZSA-N 2-hydroxyethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCO MUHFRORXWCGZGE-KTKRTIGZSA-N 0.000 description 1
- XKXPBJBODVHDAW-UHFFFAOYSA-N 4-(4-amino-2-chlorophenyl)-3-chloroaniline Chemical compound ClC1=CC(N)=CC=C1C1=CC=C(N)C=C1Cl XKXPBJBODVHDAW-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- 101710169606 Hemoglobin-2 Proteins 0.000 description 1
- 229920001612 Hydroxyethyl starch Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000004820 blood count Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HQPMKSGTIOYHJT-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2-diol Chemical compound OCCO.CC(O)CO HQPMKSGTIOYHJT-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 108010036302 hemoglobin AS Proteins 0.000 description 1
- 229940050526 hydroxyethylstarch Drugs 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/795—Porphyrin- or corrin-ring-containing peptides
- C07K14/805—Haemoglobins; Myoglobins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Gastroenterology & Hepatology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Description
【発明の詳細な説明】
本発明は、修飾ヘモグロビンを酸素運搬物質として含有
する新規代用血液に関する。
する新規代用血液に関する。
従来、代用血液に使用する酸素運搬物質として膜成分を
含まないヘモグロビンを用いることは公知である（Ｓ．
Ｆ．Ｒａｂｉｎｅ「 ｅｔ．ａｌ、Ｊ．Ｅｘ．Ｍｅｄ．
、１２６、１１４２（１９６７））。
含まないヘモグロビンを用いることは公知である（Ｓ．
Ｆ．Ｒａｂｉｎｅ「 ｅｔ．ａｌ、Ｊ．Ｅｘ．Ｍｅｄ．
、１２６、１１４２（１９６７））。
ところが、ヘモグロビンは血管内に注入されると速やか
に腎臓あるいは肝臓等から代謝されることが知られてい
る。この問題を解決するためにヘモグロビンをグルタル
アルデヒドで相互結合させたもの（持閥昭５１−６３９
２０号公報）、ヘモグロビンをデキストラン（特開昭５
２一５１０１６号公報）若し〈はヒドロキシェチル澱粉
（西独公開２６１６０８６号）に結合せしめたものに提
案された。しかしこれらのものは例えば前者は酸素親和
性が強すぎるために末梢組織での酸素の受け渡しが行わ
れにくく、また後者は粘度が高いためにヘモグロビン濃
度を上げると好ましくない結果をもたらす場合が多い。
本発明者は、ヘモグ。
に腎臓あるいは肝臓等から代謝されることが知られてい
る。この問題を解決するためにヘモグロビンをグルタル
アルデヒドで相互結合させたもの（持閥昭５１−６３９
２０号公報）、ヘモグロビンをデキストラン（特開昭５
２一５１０１６号公報）若し〈はヒドロキシェチル澱粉
（西独公開２６１６０８６号）に結合せしめたものに提
案された。しかしこれらのものは例えば前者は酸素親和
性が強すぎるために末梢組織での酸素の受け渡しが行わ
れにくく、また後者は粘度が高いためにヘモグロビン濃
度を上げると好ましくない結果をもたらす場合が多い。
本発明者は、ヘモグ。
ビンと同程度の酸素運搬能力を有し、その血管内滞留時
間が十分長い代用血液用酸素運搬物質を開発すべく鋭意
検討した結果、ヘモグロビンと、ポリエチレングリコー
ル、ポリプロピレングリコールまたはエチレングリコー
ループロピレングリコール−共重合体との結合物（以下
、「疹節ヘモグロビン」という。）がその目的を達成す
ることを見出し本発明を完成した。前記ポリエチレング
リコール、ポリプロピレングリコールおよびエチレング
リコーループロピレングリコール共重合体は本明細書に
おいてモノメチルエーテル、モノセチルエーテル、モノ
オレイルェーテル等炭素数１乃至１６のアルコールによ
るエーテル化物、モノブチルェステル、モノステァリル
ェステル等炭素数２乃至１８の脂肪酸類によるェステル
化物、プロピルアミン、ステアリルアミン等炭素数１乃
至１８のァミン類による脱水ァミノ化物をも含む。これ
ら重合物を以下単に「本発明に使用する重合体」という
。本発明に使用する修飾ヘモグロビンは、生体内に存す
るヘモグロビンと安全性の高い本発明に使用する重合体
との結合物であるので安全な物質であり、酸素親和性が
へモグ。
間が十分長い代用血液用酸素運搬物質を開発すべく鋭意
検討した結果、ヘモグロビンと、ポリエチレングリコー
ル、ポリプロピレングリコールまたはエチレングリコー
ループロピレングリコール−共重合体との結合物（以下
、「疹節ヘモグロビン」という。）がその目的を達成す
ることを見出し本発明を完成した。前記ポリエチレング
リコール、ポリプロピレングリコールおよびエチレング
リコーループロピレングリコール共重合体は本明細書に
おいてモノメチルエーテル、モノセチルエーテル、モノ
オレイルェーテル等炭素数１乃至１６のアルコールによ
るエーテル化物、モノブチルェステル、モノステァリル
ェステル等炭素数２乃至１８の脂肪酸類によるェステル
化物、プロピルアミン、ステアリルアミン等炭素数１乃
至１８のァミン類による脱水ァミノ化物をも含む。これ
ら重合物を以下単に「本発明に使用する重合体」という
。本発明に使用する修飾ヘモグロビンは、生体内に存す
るヘモグロビンと安全性の高い本発明に使用する重合体
との結合物であるので安全な物質であり、酸素親和性が
へモグ。
ピンと同程度またはやや弱いために体内での酸素の受け
渡し１こは好ましく、また血管内滞留時間もヘモグロビ
ンの２〜４倍にのび、代用血液に用いるのに好ましい化
合物である。特に、ポリエチレングリコールと蛋白との
結合物は蛋白の抗原性を消失させ得ることが知られてお
り（芦原、他、化学の領域、３３（１）、４４（１９７
９））、本発明に使用する修飾ヘモグロビンは血管内に
おいて抗原となるおそれのない安全性の高い物質である
。本発明に使用するヘモグロビンはヒト、ウシ、ブタ、
ヒツジ、ウマ、イヌ、サル、ウサギ、ニワトリ等ヘモグ
ロビンを有する動物であればいずれであっても差支えな
い。
渡し１こは好ましく、また血管内滞留時間もヘモグロビ
ンの２〜４倍にのび、代用血液に用いるのに好ましい化
合物である。特に、ポリエチレングリコールと蛋白との
結合物は蛋白の抗原性を消失させ得ることが知られてお
り（芦原、他、化学の領域、３３（１）、４４（１９７
９））、本発明に使用する修飾ヘモグロビンは血管内に
おいて抗原となるおそれのない安全性の高い物質である
。本発明に使用するヘモグロビンはヒト、ウシ、ブタ、
ヒツジ、ウマ、イヌ、サル、ウサギ、ニワトリ等ヘモグ
ロビンを有する動物であればいずれであっても差支えな
い。
ヘモグロビンに結合する本発明に使用する重合体の分子
量は３００〜２００００、性能および粘度の点で好まし
くは７５０〜５０００である。
量は３００〜２００００、性能および粘度の点で好まし
くは７５０〜５０００である。
ヘモグロビンと本発明に使用する重合体とはどのような
方法により結合させてもよく、例えば臭化シアン等の縮
合剤を用いて直接に結合させたり、あるいは塩化シアヌ
ル、２・２′ージクロロベンジジン、Ｐ・Ｐ′−ジフル
オローｍ・ｍ′−ジニトロジフエニルスルフオン、２・
４−ジクロロニトロベンゼン等の化学結合剤により結合
させればよい。
方法により結合させてもよく、例えば臭化シアン等の縮
合剤を用いて直接に結合させたり、あるいは塩化シアヌ
ル、２・２′ージクロロベンジジン、Ｐ・Ｐ′−ジフル
オローｍ・ｍ′−ジニトロジフエニルスルフオン、２・
４−ジクロロニトロベンゼン等の化学結合剤により結合
させればよい。
ヘモグロビン１分子当り、本発明に使用する重合体は４
〜１５び分子程度が結合している。
〜１５び分子程度が結合している。
本発明に使用する修飾ヘモグロビンは、例えば次の如く
して調製することができる。｛１｝ ポリエチレングリ
コールと２〜５倍モル好ましくは３倍モルの臭化シアン
とをｐＨ９〜１０で反応させた後ゲル猿週、透析等の方
法により臭化シアンを除去する。
して調製することができる。｛１｝ ポリエチレングリ
コールと２〜５倍モル好ましくは３倍モルの臭化シアン
とをｐＨ９〜１０で反応させた後ゲル猿週、透析等の方
法により臭化シアンを除去する。
得られた物質にｐＨ７〜９好まし〈は７．５〜８で水溶
液中１／Ｉ０〜１／５０の音好ましくは１／１０ぴ音モ
ル程度のヘモグロビンとを反応せしめる。‘２１ 過剰
の炭酸ソーダを含むベンゼンにポリエチレングリコール
を加え、これと２〜５倍モル好ましくは３〜４倍モルの
塩化シアヌルとを反応させ生成したポリエチレングリコ
ール−４・６−ジクロル−Ｓ−トＩＪァジンを分離する
。
液中１／Ｉ０〜１／５０の音好ましくは１／１０ぴ音モ
ル程度のヘモグロビンとを反応せしめる。‘２１ 過剰
の炭酸ソーダを含むベンゼンにポリエチレングリコール
を加え、これと２〜５倍モル好ましくは３〜４倍モルの
塩化シアヌルとを反応させ生成したポリエチレングリコ
ール−４・６−ジクロル−Ｓ−トＩＪァジンを分離する
。
ｐＨ８〜９．５の緩衝液中ポリエチレングリコールー４
・６−ジクロル−Ｓ−トリアジンと１〜１／５０の音モ
ル好ましくは１／１０〜１／１０Ｍ音モルのヘモグロビ
ンとを反応せしめる。上記調製法は、ポリエチレングリ
コールに代えてポリプロピレングリコールまたはエチレ
ングリコーループロピレングリコール共重合体を用いて
も、同様に実施することが可能である。
・６−ジクロル−Ｓ−トリアジンと１〜１／５０の音モ
ル好ましくは１／１０〜１／１０Ｍ音モルのヘモグロビ
ンとを反応せしめる。上記調製法は、ポリエチレングリ
コールに代えてポリプロピレングリコールまたはエチレ
ングリコーループロピレングリコール共重合体を用いて
も、同様に実施することが可能である。
以下実施例により本発明を詳細に説明する。
実施例 １ポリエチレングリコ−ルモノメチルエーテル
（平均分子量７５０）２．５夕（０．００３モル）を４
０の‘の水に溶解し、これに５の‘のジキオサンに溶解
した１夕（０．００９５モル）の臭化シアンを氷冷化滴
下した。州ＮａＯＨによりＰＨ９〜１０に保ちつつ１時
間縄拝を続けた。ＩＮＨＣＩによりｐＨ７．５に調製し
たのち分子量５０瓜阻止のメンブランにより限外濠週を
行った。２０の‘まで濃縮したのちｐＨ７．５のリン酸
緩衝液３００の‘を加え再度２０Ｍまで濃縮した。
（平均分子量７５０）２．５夕（０．００３モル）を４
０の‘の水に溶解し、これに５の‘のジキオサンに溶解
した１夕（０．００９５モル）の臭化シアンを氷冷化滴
下した。州ＮａＯＨによりＰＨ９〜１０に保ちつつ１時
間縄拝を続けた。ＩＮＨＣＩによりｐＨ７．５に調製し
たのち分子量５０瓜阻止のメンブランにより限外濠週を
行った。２０の‘まで濃縮したのちｐＨ７．５のリン酸
緩衝液３００の‘を加え再度２０Ｍまで濃縮した。
氷冷下縄拝しつつ１０％ヘモグロビン溶液２０の上を加
え４℃に一夜放置した。ｐＨ６．０に平衡化したＣＭー
セフアデックス樹脂に反応液を通してヘモグロビンおよ
び生成物を吸着させた後ｐＨ６．８のリン酸緩衝液によ
り溶麹する画分を分離した。分子量５方阻止のメンブラ
ンにより限外櫨過を行い脱塩、濃縮後０．４＆メンブラ
ンにより猿過し、乾燥後、ポリエチレングリコ−ルモノ
メチルェーテルが結合したヘモグロビン３．５夕を得た
。ポリエチレングリコ‐ルモノメチルエーテルの置換度
は約１０であった。
え４℃に一夜放置した。ｐＨ６．０に平衡化したＣＭー
セフアデックス樹脂に反応液を通してヘモグロビンおよ
び生成物を吸着させた後ｐＨ６．８のリン酸緩衝液によ
り溶麹する画分を分離した。分子量５方阻止のメンブラ
ンにより限外櫨過を行い脱塩、濃縮後０．４＆メンブラ
ンにより猿過し、乾燥後、ポリエチレングリコ−ルモノ
メチルェーテルが結合したヘモグロビン３．５夕を得た
。ポリエチレングリコ‐ルモノメチルエーテルの置換度
は約１０であった。
実施例 ２
ポリエチレングリコ一ルモノメチルエーテル（平均分子
量７５０）７．５夕（０．０１モル）を５００の‘のベ
ンゼンに溶解し、炭酸ソーダ１０夕を加えた。
量７５０）７．５夕（０．０１モル）を５００の‘のベ
ンゼンに溶解し、炭酸ソーダ１０夕を加えた。
氷冷下、激しく鷹拝しつつ塩化シアヌル５．５夕（０．
０３モル）を加えた後、室温にて一夜縄拝した。炭酸ソ
ーダを猿過後、石油エーテル（沸点３０〜７０ｑｏ）１
そを加えると２−○ーメトキシポリェチレングリコール
−４・６ージクロロ−Ｓ−トリアジン（活性化ポリエチ
レングリコール）が沈澱した。この結晶を石油エーテル
でよく洗った後乾燥した（１１．５夕）。ヘモグロビン
０．５夕（０．００７７ミリモル）を１００泌のホゥ酸
緩衝液（ｐＨ９．２）に溶解した溶液に氷冷下上記活性
化ポリエチレングリコール１．７夕（１．８ミリモル）
を加えた。１時間氷冷下礎洋した後分子量１０方阻止メ
ンプランにより限外渡過を繰返し未反応ヘモグロビンお
よび活性化ポリエチレングリコ、一ルを猿別後乾燥する
ことにより修飾ヘモグロビン２．６夕を得た。
０３モル）を加えた後、室温にて一夜縄拝した。炭酸ソ
ーダを猿過後、石油エーテル（沸点３０〜７０ｑｏ）１
そを加えると２−○ーメトキシポリェチレングリコール
−４・６ージクロロ−Ｓ−トリアジン（活性化ポリエチ
レングリコール）が沈澱した。この結晶を石油エーテル
でよく洗った後乾燥した（１１．５夕）。ヘモグロビン
０．５夕（０．００７７ミリモル）を１００泌のホゥ酸
緩衝液（ｐＨ９．２）に溶解した溶液に氷冷下上記活性
化ポリエチレングリコール１．７夕（１．８ミリモル）
を加えた。１時間氷冷下礎洋した後分子量１０方阻止メ
ンプランにより限外渡過を繰返し未反応ヘモグロビンお
よび活性化ポリエチレングリコ、一ルを猿別後乾燥する
ことにより修飾ヘモグロビン２．６夕を得た。
置換度：約５０。実施例 ３ポリエチレングリコ−ルモ
ノメチルエーテル（平均分子量１９００）１９夕（０．
０１モル）、４００Ｍのベンゼン、炭酸ソーダ１０夕お
よび塩化シアヌル５．５夕（０．０３モル）を用いて、
実施例２と同機の反応、処理を行い活性化ポリエチレン
グリコール２４夕を得た。
ノメチルエーテル（平均分子量１９００）１９夕（０．
０１モル）、４００Ｍのベンゼン、炭酸ソーダ１０夕お
よび塩化シアヌル５．５夕（０．０３モル）を用いて、
実施例２と同機の反応、処理を行い活性化ポリエチレン
グリコール２４夕を得た。
ヘモグロビン２夕（０．０３１ミリモル）、２０物‘の
ホウ酸緩衝液（ｐＨ９．２）および活性化ポリエチレン
グリコール６．４夕（３．１ミリモル）を用いて実施例
２と同様の反応、精製操作を行し、疹節ヘモグロビンを
７．６タ得た。置換度：約８０。実施例 ４ポリエチレ
ングリコ一ルモノメチルエーテル（平均分子量５０００
）５０夕（０．０１モル）、５００の‘のベンゼン、１
０夕の炭酸ソーダおよび５．５夕（０．０３モル）の塩
化シアヌルを用いて実施例２と同様の反応、処理を行い
活性化ポリエチレングリコール５３夕を得た。
ホウ酸緩衝液（ｐＨ９．２）および活性化ポリエチレン
グリコール６．４夕（３．１ミリモル）を用いて実施例
２と同様の反応、精製操作を行し、疹節ヘモグロビンを
７．６タ得た。置換度：約８０。実施例 ４ポリエチレ
ングリコ一ルモノメチルエーテル（平均分子量５０００
）５０夕（０．０１モル）、５００の‘のベンゼン、１
０夕の炭酸ソーダおよび５．５夕（０．０３モル）の塩
化シアヌルを用いて実施例２と同様の反応、処理を行い
活性化ポリエチレングリコール５３夕を得た。
１０％ヘモグロビン溶液２０舷、４５０の‘のホウ酸緩
衝液（ｐＨ９．２）および４０夕の活性化ポリＪエチレ
ングリコールを用いて実施例２と同様の反応、精製操作
を行い修飾ヘモグロビン３４夕を得た。
衝液（ｐＨ９．２）および４０夕の活性化ポリＪエチレ
ングリコールを用いて実施例２と同様の反応、精製操作
を行い修飾ヘモグロビン３４夕を得た。
置換度：１０５。実施例 ５
ポリエチレングリコール（平均分子量２００００）Ｚ４
Ｍ（０．００２モル）、ベンゼン１夕、炭酸ソーダ１０
夕および塩化シアヌル１．１夕（０．００６モル）を加
え、室温にて一夜楓拝した。
Ｍ（０．００２モル）、ベンゼン１夕、炭酸ソーダ１０
夕および塩化シアヌル１．１夕（０．００６モル）を加
え、室温にて一夜楓拝した。
石油エーテル１夕を加えて生じた沈澱を用いて実施例２
と同様の反応、処理を行い活性化ポリエチレングリコー
ル３９２夕が得られた。４００の【のホウ酸緩衝液（ｐ
Ｈ９．２）に１０％ヘモグロビン溶液２０の‘（０．０
０００３モル）を加えて氷冷下上記活性化ポリエチレン
グリコール１０夕（０．０００５モル）を加え１時間損
拝を行った。
と同様の反応、処理を行い活性化ポリエチレングリコー
ル３９２夕が得られた。４００の【のホウ酸緩衝液（ｐ
Ｈ９．２）に１０％ヘモグロビン溶液２０の‘（０．０
０００３モル）を加えて氷冷下上記活性化ポリエチレン
グリコール１０夕（０．０００５モル）を加え１時間損
拝を行った。
分子量１０万阻止のメンブランで限外猿過し濃縮後ｐＨ
６．０のリン酸緩衝液で平衡化したＣＭ−セフアデック
スに吸着させた後、ｐＨ６．３のリン酸緩衝液で溶離す
る分画を捨て、次にｐＨ６．８のリン酸緩衝液で漆離す
る分画を分離した。この分画を分子量１０万阻止のメン
ブランで濃縮して修飾ヘモグロビン３夕を得た。置換度
：約４。実施例 ６ ポリエチレングリコールモノステアリルエステル（平均
分子量２５００）１２．５夕（０．００５モル）、４０
０の‘のベンゼン、炭酸ソーダ５夕および塩化シアヌル
２．７５夕（０．０１５モル）を用いて実施例２と同様
の反応、処理を行い活性化ポリエチレングリコール１３
．５夕を得た。
６．０のリン酸緩衝液で平衡化したＣＭ−セフアデック
スに吸着させた後、ｐＨ６．３のリン酸緩衝液で溶離す
る分画を捨て、次にｐＨ６．８のリン酸緩衝液で漆離す
る分画を分離した。この分画を分子量１０万阻止のメン
ブランで濃縮して修飾ヘモグロビン３夕を得た。置換度
：約４。実施例 ６ ポリエチレングリコールモノステアリルエステル（平均
分子量２５００）１２．５夕（０．００５モル）、４０
０の‘のベンゼン、炭酸ソーダ５夕および塩化シアヌル
２．７５夕（０．０１５モル）を用いて実施例２と同様
の反応、処理を行い活性化ポリエチレングリコール１３
．５夕を得た。
１０％ヘモグロビン溶液２５の【（０．０４ミリモル）
、９００の【ホウ酸緩衝液（ｐＨ９．２）および上記活
性化ポリエチレングリコール１０．５夕（０．００４モ
ル）を用いて実施例２と同様の反応、精製操作を行い修
飾ヘモグロビン８夕を得た。
、９００の【ホウ酸緩衝液（ｐＨ９．２）および上記活
性化ポリエチレングリコール１０．５夕（０．００４モ
ル）を用いて実施例２と同様の反応、精製操作を行い修
飾ヘモグロビン８夕を得た。
置換度：約９０。実施例 ７
ポリエチレングリコ一ルモノオレイエーテル（平均分子
量１０００）５夕（０．００５モル）、４００叫のベン
ゼン、炭酸ソーダ５夕および塩化シアヌル２．７５夕（
０．０１５モル）を用いて実施例２と同様の反応、処理
を行い活性化ポリェチレソグＩＪコール６夕を得た。
量１０００）５夕（０．００５モル）、４００叫のベン
ゼン、炭酸ソーダ５夕および塩化シアヌル２．７５夕（
０．０１５モル）を用いて実施例２と同様の反応、処理
を行い活性化ポリェチレソグＩＪコール６夕を得た。
牛ヘモグロビン（シグマ社製）１．３夕（０．０２ミリ
モル）、４５０の‘ホゥ酸緩衝液（ｐＨ９．２）および
上記活性化ポリエチレングリコール５．３夕（０．００
２モル）を用いて実施例２と同様の反応、精製操作を行
い修飾ヘモグロビン４．２夕を得た。置換度：約８を実
施例 ８ ポリプロピレングリコール（平均分子量４０００）１２
夕（０．００３モル）を水１２０舷に溶解し、これに実
施例１と同様の操作により臭化シアン（０．００９５モ
ル）を反応、濃縮を行った。
モル）、４５０の‘ホゥ酸緩衝液（ｐＨ９．２）および
上記活性化ポリエチレングリコール５．３夕（０．００
２モル）を用いて実施例２と同様の反応、精製操作を行
い修飾ヘモグロビン４．２夕を得た。置換度：約８を実
施例 ８ ポリプロピレングリコール（平均分子量４０００）１２
夕（０．００３モル）を水１２０舷に溶解し、これに実
施例１と同様の操作により臭化シアン（０．００９５モ
ル）を反応、濃縮を行った。
豚ヘモグロビン（シグマ社製）２夕を実施例１と同様の
操作で反応させた後、分離、精製を行い修飾へモグ。ピ
ン７夕を得た。ポリプロピレングリコールの置換度は約
３０であった。本発明で得られる化合物、修飾ヘモグロ
ビンについて血管内滞留時間および酸素新和力を調べた
。
操作で反応させた後、分離、精製を行い修飾へモグ。ピ
ン７夕を得た。ポリプロピレングリコールの置換度は約
３０であった。本発明で得られる化合物、修飾ヘモグロ
ビンについて血管内滞留時間および酸素新和力を調べた
。
一試料につきラット（平均体重：３５０夕）二匹を用い
、ラットの体重に対し５の【／ｋ９の４〜６％修飾ヘモ
グロビンを静柱後５分、ＩＣ分、１８分、３０分、６ひ
分、９０分、１２０分経過時に０．５の‘ずつ採血し、
遠心処理後血数中の修飾ヘモグロビン量をシアンメトヘ
モグロビン法により比色定草した。
、ラットの体重に対し５の【／ｋ９の４〜６％修飾ヘモ
グロビンを静柱後５分、ＩＣ分、１８分、３０分、６ひ
分、９０分、１２０分経過時に０．５の‘ずつ採血し、
遠心処理後血数中の修飾ヘモグロビン量をシアンメトヘ
モグロビン法により比色定草した。
そのグラフから注入した修飾ヘモグロビンの血鰍中での
半減期を計算した。結果を表１に示す。表１ 十 実施例１〜４の方法により調製した修飾ヘモグロビン溶
液（０．１Ｍ ＮａＣＩ溶液、ｐＨ７．４０）をＡｍｉ
ｍｏ社製Ｈｅｍ−○−Ｓｃａｎ装置を用い、酸素平衡曲
線を描き、それから５０％酸素解離圧（Ｐ５０値）を求
めた。
半減期を計算した。結果を表１に示す。表１ 十 実施例１〜４の方法により調製した修飾ヘモグロビン溶
液（０．１Ｍ ＮａＣＩ溶液、ｐＨ７．４０）をＡｍｉ
ｍｏ社製Ｈｅｍ−○−Ｓｃａｎ装置を用い、酸素平衡曲
線を描き、それから５０％酸素解離圧（Ｐ５０値）を求
めた。
結果を表２に示す。表２
Claims (1)
- １ 酸素運搬物質を含有する代用血液において、酸素運
搬物質がヘモグロビンと、ポリエチレングリコール、ポ
リプロピレングリコールまたはエチレングリコール−プ
ロピレングリコール共重合体との結合物であることを特
徴とする代用血液。
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54087910A JPS6023084B2 (ja) | 1979-07-11 | 1979-07-11 | 代用血液 |
| US06/167,360 US4301144A (en) | 1979-07-11 | 1980-07-10 | Blood substitute containing modified hemoglobin |
| GB8022583A GB2055868B (en) | 1979-07-11 | 1980-07-10 | Blood substitute containing hemoglobin |
| FR8015568A FR2460674A1 (fr) | 1979-07-11 | 1980-07-11 | Succedane du sang contenant de l'hemoglobine modifiee |
| DE19803026398 DE3026398A1 (de) | 1979-07-11 | 1980-07-11 | Modifiziertes haemoglobin enthaltender blutersatz |
| CA000356067A CA1146858A (en) | 1979-07-11 | 1980-07-11 | Blood substitute containing modified hemoglobin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54087910A JPS6023084B2 (ja) | 1979-07-11 | 1979-07-11 | 代用血液 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5612308A JPS5612308A (en) | 1981-02-06 |
| JPS6023084B2 true JPS6023084B2 (ja) | 1985-06-05 |
Family
ID=13928063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54087910A Expired JPS6023084B2 (ja) | 1979-07-11 | 1979-07-11 | 代用血液 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4301144A (ja) |
| JP (1) | JPS6023084B2 (ja) |
| CA (1) | CA1146858A (ja) |
| DE (1) | DE3026398A1 (ja) |
| FR (1) | FR2460674A1 (ja) |
| GB (1) | GB2055868B (ja) |
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| WO2025235919A1 (en) | 2024-05-09 | 2025-11-13 | Takeda Pharmaceutical Company Limited | Dosing regimens of anti-cd38 antibodies for treatment of subjects with immunoglobulin a nephropathy |
| WO2025242845A1 (en) | 2024-05-22 | 2025-11-27 | Merck Patent Gmbh | Colorectal cancer treatment |
| WO2025254987A1 (en) | 2024-06-03 | 2025-12-11 | Alector Llc | Siglec-9 ecd fusion molecule variants and methods of use thereof |
| WO2026024904A1 (en) | 2024-07-24 | 2026-01-29 | Gigagen, Inc. | Custom recombinant polyclonal proteins and methods of use thereof |
| WO2026033259A1 (en) | 2024-08-05 | 2026-02-12 | Lys Therapeutics | Antibodies for treating neurological and neurovascular disorders |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001401A (en) * | 1975-02-02 | 1977-01-04 | Alza Corporation | Blood substitute and blood plasma expander comprising polyhemoglobin |
| CA1055932A (en) * | 1975-10-22 | 1979-06-05 | Hematech Inc. | Blood substitute based on hemoglobin |
-
1979
- 1979-07-11 JP JP54087910A patent/JPS6023084B2/ja not_active Expired
-
1980
- 1980-07-10 US US06/167,360 patent/US4301144A/en not_active Expired - Lifetime
- 1980-07-10 GB GB8022583A patent/GB2055868B/en not_active Expired
- 1980-07-11 DE DE19803026398 patent/DE3026398A1/de active Granted
- 1980-07-11 CA CA000356067A patent/CA1146858A/en not_active Expired
- 1980-07-11 FR FR8015568A patent/FR2460674A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2055868A (en) | 1981-03-11 |
| JPS5612308A (en) | 1981-02-06 |
| GB2055868B (en) | 1983-04-07 |
| DE3026398A1 (de) | 1981-03-26 |
| CA1146858A (en) | 1983-05-24 |
| FR2460674B1 (ja) | 1983-06-24 |
| FR2460674A1 (fr) | 1981-01-30 |
| DE3026398C2 (ja) | 1990-09-13 |
| US4301144A (en) | 1981-11-17 |
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