Maghraby Amany, Bahgat Mahmoud
Medicinal Chemistry Department, National Research Centre, Dokki, Cairo, Egypt.
Arzneimittelforschung. 2004;54(9):545-50. doi: 10.1055/s-0031-1297010.
Coumarins (pyranobenzopyran derivatives) (coumarin: CAS 91-64-5), organic compounds of known chemotherapeutic importance against bacteria, infectious diseases and tumors, were tested for their immunomodulatory effects. The compounds used in the present study were 1H,9H-3-amino-7-methyl-9-oxo-1-phenylpyran(2,3-h)(1)benzopyran-2-carbonitrile; 1H,9H-2-carboxamido-7-methyl-3,9-dioxo-1-phenylpyran(2,3-h)(1)benzopyran; 4H,8H-2-amino-7-bromo-6-methyl-10-nitro-8-oxo-4-(p-nitrophenyl)-pyran(3,2-g)(1)benzopyran-3-carbonitrile; 4H-7-bromo-3-carboxamido-2,8-dioxo-6-methyl-10-nitro-4-(p-nitrophenyl)2,8-dihydropyran(3,2g)(1) benzopyran. Mice were injected subcutaneously (0.75 mg/mouse) with each of the compounds for three successive days, then each animal was exposed to 100 Schistosoma mansoni cercariae. The effect on the humoral immune response was detected by measuring immunoglbulin G (IgG) levels using enzyme-linked immunosorbent assay (ELISA) against E. coli lysate, soluble worm antigen preparation (SWAP) and cancer bladder tissue homogenates. The reactivity of IgG to E. coli lysate was measured in sera of treated mice before and after infection. However, for SWAP and cancer tissue homogenates the IgG was measured only after infection. Mice given compounds 2, 3 and 4 showed a concentration dependent increase in IgG level against E. coli lysate as compared to untreated uninfected mice. Animals given compounds 3 and 4 followed by S. mansoni infection showed a significant increase (p< 0.05) in IgG level against the same antigen. Moreover, compounds 1, 2 and 4 significantly (p < 0.05) stimulated IgG production when measured against SWAP. Compounds 2, 3 and 4 induced a significant (p < 0.05) IgG response to cancer bladder tissue homogenates as compared to infected control mice. At the cellular level, treatment with compounds 1, 2, 3 and 4 caused a significant increase (p < 0.05) in the mean percentage of CD4+-T cells as compared with normal control, whereas, compounds 1, 2 and 3 stimulated a significant increase (p < 0.05) in the mean percentage of CD8+-T cells. Six weeks post-infection compounds 3 and 4 induced a significant stimulation (p< 0.05) in the mean number of both CD4+ and CD8+-T cells. The study showed that the compounds used have an immunomodulatory effect at both humoral and cellular levels.
香豆素(吡喃并苯并吡喃衍生物)(香豆素:CAS 91-64-5)是已知对细菌、传染病和肿瘤具有化疗重要性的有机化合物,对其免疫调节作用进行了测试。本研究中使用的化合物为1H,9H-3-氨基-7-甲基-9-氧代-1-苯基吡喃(2,3-h)(1)苯并吡喃-2-腈;1H,9H-2-羧酰胺基-7-甲基-3,9-二氧代-1-苯基吡喃(2,3-h)(1)苯并吡喃;4H,8H-2-氨基-7-溴-6-甲基-10-硝基-8-氧代-4-(对硝基苯基)-吡喃(3,2-g)(1)苯并吡喃-3-腈;4H-7-溴-3-羧酰胺基-2,8-二氧代-6-甲基-10-硝基-4-(对硝基苯基)2,8-二氢吡喃(3,2g)(1)苯并吡喃。将每种化合物以皮下注射方式(0.75毫克/只小鼠)连续三天注射给小鼠,然后使每只动物暴露于100条曼氏血吸虫尾蚴。通过使用酶联免疫吸附测定(ELISA)针对大肠杆菌裂解物、可溶性虫体抗原制剂(SWAP)和癌性膀胱组织匀浆测量免疫球蛋白G(IgG)水平,检测对体液免疫反应的影响。在感染前后测量处理过的小鼠血清中IgG对大肠杆菌裂解物的反应性。然而,对于SWAP和癌组织匀浆,仅在感染后测量IgG。与未处理的未感染小鼠相比,给予化合物2、3和4的小鼠针对大肠杆菌裂解物的IgG水平呈浓度依赖性增加。给予化合物3和4后再感染曼氏血吸虫的动物,针对相同抗原的IgG水平显著增加(p<0.05)。此外,当针对SWAP测量时,化合物1、2和4显著(p<0.05)刺激IgG产生。与感染对照小鼠相比,化合物2、3和4诱导对癌性膀胱组织匀浆产生显著(p<0.05)的IgG反应。在细胞水平上,与正常对照相比,用化合物1、2、3和4处理导致CD4+ -T细胞平均百分比显著增加(p<0.05),而化合物1、2和3刺激CD8+ -T细胞平均百分比显著增加(p<0.05)。感染六周后,化合物3和4诱导CD4+和CD8+ -T细胞平均数量显著增加(p<0.05)。该研究表明,所使用的化合物在体液和细胞水平上均具有免疫调节作用。