Lüllmann-Rauch R, Pods R, von Witzendorff B
Department of Anatomy, University of Kiel, Germany.
Toxicology. 1996 Jun 17;110(1-3):27-37. doi: 10.1016/0300-483x(96)03319-7.
The antimalarial agents quinacrine and chloroquine are well known as potent inducers of lysosomal storage of polar lipids (lipidosis) in cell culture and in vivo. In previous experiments on cultured fibroblasts, chloroquine was shown to additionally cause weak lysosomal storage of sulphated glycosaminoglycans (GAGs) thus inducing mucopolysaccharidosis (MPS). In the present study, quinacrine was investigated for this ability, because we wished to know whether or not the acridine ring system in quinacrine would enhance the MPS-inducing potency as compared to chloroquine carrying an isoquinoline ring system. Tilorone (2,7-bis[2-(diethylamino)ethoxy]fluoren-9-one) known as a potent inducer of MPS served as reference compound. The compounds were compared at a concentration (3 microM) which did not enhance the secretion of the lysosomal enzyme beta-hexosaminidase (E.C. 3.2.1.52), since this would be an indication of unspecific drug effects upon the endosomal/lysosomal compartments of the cell. Additionally the liver of quinacrine- and chloroquine-treated rats was examined with the question whether the lysosomal GAG storage induced by either drug in cell culture had an equivalent in intact organisms. Both, in cell culture and in vivo, quinacrine was found to be a more potent inducer of lysosomal GAG storage than was chloroquine. The results suggest that the acridine ring system favours this drug side effect as compared with the bicyclic isoquinoline ring system. On the other hand, quinacrine was significantly less potent than tilorone and the Symmetrically substituted acridine derivative 3,6-bis[2-(diethylamino)ethoxy]acridine investigated previously. This suggests that the asymmetric structure of the quinacrine molecule reduces the potency as compared to the symmetrically substituted bisbasic compounds with planary tricyclic ring systems such as tilorone and congeners.
抗疟药阿的平和氯喹在细胞培养和体内作为极性脂质溶酶体储存(脂质沉积症)的有效诱导剂而广为人知。在先前对培养的成纤维细胞进行的实验中,氯喹还被证明会导致硫酸化糖胺聚糖(GAGs)在溶酶体中轻度储存,从而诱发黏多糖贮积症(MPS)。在本研究中,对阿的平的这种能力进行了研究,因为我们想知道与带有异喹啉环系统的氯喹相比,阿的平中的吖啶环系统是否会增强诱发MPS的效力。已知作为MPS有效诱导剂的替洛隆(2,7-双[2-(二乙氨基)乙氧基]芴-9-酮)用作参考化合物。以不增强溶酶体酶β-己糖胺酶(E.C. 3.2.1.52)分泌的浓度(3 microM)对这些化合物进行比较,因为这将表明药物对细胞内体/溶酶体区室有非特异性作用。此外,还检查了用阿的平和氯喹处理的大鼠的肝脏,以探讨在细胞培养中由这两种药物诱导的溶酶体GAG储存是否在完整生物体中也存在。在细胞培养和体内,均发现阿的平是比氯喹更有效的溶酶体GAG储存诱导剂。结果表明,与双环异喹啉环系统相比,吖啶环系统更易引发这种药物副作用。另一方面,阿的平的效力明显低于替洛隆和先前研究的对称取代的吖啶衍生物3,6-双[2-(二乙氨基)乙氧基]吖啶。这表明,与具有平面三环系统的对称取代的双碱性化合物(如替洛隆及其同系物)相比,阿的平分子的不对称结构降低了其效力。