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合成的6-O-酰基-N-乙酰基胞壁酰-L-丙氨酰-D-异谷氨酰胺的免疫佐剂活性，特别提及与脂质体联合给药的效果。

Immunoadjuvant activities of synthetic 6-O-acyl-N-acetylmuramyl-L-alanyl-D-isoglutamine with special reference to the effect of its administration with liposomes.

作者信息

Kotani S, Kinoshita F, Morisaki I, Shimono T, Okunaga T, Takada H, Tsujimoto M, Watanabe Y, Kato K, Shiba T, Kusumoto S, Okada S

出版信息

Biken J. 1977 Dec;20(3-4):95-103.

PMID:614856
Abstract

Addition of a lauroyl, stearoyl or docosanoyl group to the primary hydroxy group at the C-6 position of N-acetylmuramyl-L-alanyl-D-isoglutamine gave lipophilic derivatives that had definite adjuvancies in induction of delayed-type hypersensitivity and enhancement of antibody production against a test protein antigen, ovalbumin, when administered to guinea pigs as liposomes, that is without mineral oil. When administered as mineral oil-in-water emulsion, including Ribitype emulsions, rather than as water-in-mineral oil emulsions, N-acetylmuramyl-L-alanyl-D-isoglutamine and its 6-O-acyl derivatives showed only weak immunoadjuvancies.

摘要

在N - 乙酰胞壁酰 - L - 丙氨酰 - D - 异谷氨酰胺的C - 6位伯羟基上添加月桂酰基、硬脂酰基或二十二烷酰基，可得到亲脂性衍生物。当以脂质体形式（即不含矿物油）给豚鼠注射时，这些衍生物在诱导迟发型超敏反应和增强针对测试蛋白抗原卵清蛋白的抗体产生方面具有明确的佐剂作用。当以水包油乳液（包括核糖型乳液）而非油包水乳液形式给药时，N - 乙酰胞壁酰 - L - 丙氨酰 - D - 异谷氨酰胺及其6 - O - 酰基衍生物仅表现出微弱的免疫佐剂作用。

相似文献

1
Immunoadjuvant activities of synthetic 6-O-acyl-N-acetylmuramyl-L-alanyl-D-isoglutamine with special reference to the effect of its administration with liposomes.合成的6-O-酰基-N-乙酰基胞壁酰-L-丙氨酰-D-异谷氨酰胺的免疫佐剂活性，特别提及与脂质体联合给药的效果。
Biken J. 1977 Dec;20(3-4):95-103.
2
The effect of replacement of L-alanine residue by glycine, L-serine or D-alanine in an N-acetylmuramyl-L-alanyl-D-isoglutamine on immunoadjuvancies of molecules.在N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺中用甘氨酸、L-丝氨酸或D-丙氨酸取代L-丙氨酸残基对分子免疫佐剂活性的影响。
Biken J. 1977 Jun;20(2):39-45.
3
Immunoadjuvant activities of synthetic N-acetyl-muramyl-peptides or -amino acids.合成的N-乙酰胞壁酰肽或氨基酸的免疫佐剂活性。
Biken J. 1975 Jun;18(2):105-11.
4
Immunoadjuvant activities of cell walls, their water-soluble fractions and peptidoglycan subunits, prepared from various gram-positive bacteria, and of synthetic n-acetylmuramyl peptides.从各种革兰氏阳性菌制备的细胞壁、其水溶性组分和肽聚糖亚基以及合成的N-乙酰胞壁酰肽的免疫佐剂活性。
Z Immunitatsforsch Exp Klin Immunol. 1975 Jul;149(2-4):302-19.
5
Immunoadjuvant activities of peptidoglycan subunits from the cell walls of Staphyloccus aureus and Lactobacillus plantarum.金黄色葡萄球菌和植物乳杆菌细胞壁中肽聚糖亚基的免疫佐剂活性
Biken J. 1975 Jun;18(2):93-103.
6
Adjuvant activity of 6-O-mycoloyl derivatives of N-acetylmuramyl-L-seryl-D-isoglutamine and related compounds in mice and guinea pigs.N-乙酰胞壁酰-L-丝氨酰-D-异谷氨酰胺的6-O-霉菌酰衍生物及相关化合物在小鼠和豚鼠中的佐剂活性
Infect Immun. 1979 Apr;24(1):83-9. doi: 10.1128/iai.24.1.83-89.1979.
7
Acute and chronic polyarthritis induced by an aqueous form of 6-O-acyl and N-acyl derivatives of N-acetylmuramyl-L-alanyl-D-isoglutamine in euthymic rats and athymic nude rats.在正常大鼠和无胸腺裸鼠中，由N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺的6-O-酰基和N-酰基衍生物的水性形式诱导的急性和慢性多关节炎。
Lab Invest. 1986 Sep;55(3):337-46.
8
Correlation between the immunoadjuvant activities and pyrogenicities of synthetic N-acetylmuramyl-peptides or -amino acids.合成的N-乙酰胞壁酰肽或 -氨基酸的免疫佐剂活性与致热活性之间的相关性。
Biken J. 1976 Mar;19(1):9-13.
9
Enhancement of serum antibody production in mice by oral administration of lipophilic derivatives of muramylpeptides and bacterial lipopolysaccharides with bovine serum albumin.通过口服给予带有牛血清白蛋白的胞壁酰肽和亲脂性衍生物及细菌脂多糖增强小鼠血清抗体产生
Methods Find Exp Clin Pharmacol. 1986 Jan;8(1):19-26.
10
Immunoadjuvant effects of the synthetic muramyl-dipeptide (MDP) N-acetylmuramyl-L-alanyl-D-isoglutamine.合成的胞壁酰二肽（MDP）N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺的免疫佐剂作用。
Z Immunitatsforsch Immunobiol. 1978 Oct;155(1):87-92.

引用本文的文献

1
Immunostimulant activities of a lipophilic muramyl dipeptide derivative and of desmuramyl peptidolipid analogs.一种亲脂性胞壁酰二肽衍生物和去胞壁酰肽脂类似物的免疫刺激活性。
Infect Immun. 1980 Mar;27(3):826-31. doi: 10.1128/iai.27.3.826-831.1980.
2
Adjuvant activity of 6-amino-6-deoxy-muramyldipeptides and their acylamino derivatives on the induction of delayed hypersensitivity to azobenzenearsonate-N-acetyl-L-tyrosine in guinea pigs.6-氨基-6-脱氧-胞壁酰二肽及其酰氨基衍生物对豚鼠诱导对偶氮苯砷酸盐-N-乙酰-L-酪氨酸迟发型超敏反应的佐剂活性。
Infect Immun. 1981 Jun;32(3):1305-8. doi: 10.1128/iai.32.3.1305-1308.1981.
3
Muramyl peptides. Chemical structure, biological activity and mechanism of action.
胞壁酰肽。化学结构、生物活性及作用机制。
Mol Cell Biochem. 1981 Dec 4;41:27-47. doi: 10.1007/BF00225295.
4
Stimulation of nonspecific resistance to infection induced by 6-O-acyl muramyl dipeptide analogs in mice.6-O-酰基胞壁酰二肽类似物对小鼠感染非特异性抵抗力的刺激作用。
Infect Immun. 1981 May;32(2):748-58. doi: 10.1128/iai.32.2.748-758.1981.
5
Chemical and biological properties of a peptidoglycan isolated from Treponema pallidum kazan.从梅毒螺旋体 kazan 分离出的肽聚糖的化学和生物学特性。
Infect Immun. 1981 Feb;31(2):767-74. doi: 10.1128/iai.31.2.767-774.1981.
6
Relationship of anti-tuberculous protection to lung granuloma produced by intravenous injection of synthetic 6-O-mycoloyl-N-acetylmuramyl-L-alanyl-D-isoglutamine with or without specific antigens.静脉注射合成的6-O-分枝菌酰基-N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺（无论有无特异性抗原）所产生的抗结核保护作用与肺肉芽肿的关系。
Immunology. 1980 Aug;40(4):557-64.
7
Eradication of spontaneous metastases and activation of alveolar macrophages by intravenous injection of liposomes containing muramyl dipeptide.通过静脉注射含胞壁酰二肽的脂质体消除自发性转移并激活肺泡巨噬细胞。
Proc Natl Acad Sci U S A. 1981 Mar;78(3):1680-4. doi: 10.1073/pnas.78.3.1680.
8
Induction of syngeneic tumour-specific immunity by liposomes reconstituted with L2C tumour-cell antigens.用L2C肿瘤细胞抗原重构的脂质体诱导同基因肿瘤特异性免疫。
Immunology. 1983 Jul;49(3):431-8.
9
Marked enhancement in vivo of adjuvant activity of muramyl dipeptide to protein antigens and to synthetic weak immunogens with monoclonal anti-muramyl dipeptide antibodies.用单克隆抗胞壁酰二肽抗体在体内显著增强胞壁酰二肽对蛋白质抗原和合成弱免疫原的佐剂活性。
Infect Immun. 1985 Aug;49(2):312-9. doi: 10.1128/iai.49.2.312-319.1985.
10
Adjuvant activity of 6-O-acyl-muramyldipeptides to enhance primary cellular and humoral immune responses in guinea pigs: adaptability to various vehicles and pyrogenicity.6-O-酰基-胞壁酰二肽增强豚鼠初次细胞免疫和体液免疫反应的佐剂活性：对各种载体的适应性和致热原性。
Infect Immun. 1986 Sep;53(3):511-6. doi: 10.1128/iai.53.3.511-516.1986.