Université de Lorraine, CITHEFOR, F-54000 Nancy, France.
Université de Lorraine, CITHEFOR, F-54000 Nancy, France.
Biochem Pharmacol. 2018 Sep;155:21-31. doi: 10.1016/j.bcp.2018.06.018. Epub 2018 Jun 21.
S-Nitrosothiols, a class of NO donors, demonstrate potential benefits for cardiovascular diseases. Drugs for such chronic diseases require long term administration preferentially through the oral route. However, the absorption of S-nitrosothiols by the intestine, which is the first limiting barrier for their vascular bioavailability, is rarely evaluated. Using an in vitro model of intestinal barrier, based on human cells, the present work aimed at elucidating the mechanisms of intestinal transport (passive or active, paracellular or transcellular pathway) and at predicting the absorption site of three S-nitrosothiols: S-nitrosoglutathione (GSNO), S-nitroso-N-acetyl-l-cysteine (NACNO) and S-nitroso-N-acetyl-d-penicillamine (SNAP). These S-nitrosothiols include different skeletons carrying the nitroso group, which confer different physico-chemical characteristics and biological activities (antioxidant and anti-inflammatory). According to the values of apparent permeability coefficient, the three S-nitrosothiols belong to the medium class of permeability. The evaluation of the bidirectional apparent permeability demonstrated a passive diffusion of the three S-nitrosothiols. GSNO and NACNO preferentially cross the intestinal barrier though the transcellular pathway, while SNAP followed both the trans- and paracellular pathways. Finally, the permeability of NACNO was favoured at pH 6.4, which is close to the pH of the jejunal part of the intestine. Through this study, we determined the absorption mechanisms of S-nitrosothiols and postulated that they can be administrated through the oral route.
S-亚硝基硫醇是一类一氧化氮供体,对心血管疾病具有潜在益处。此类慢性疾病的药物优选通过口服途径长期给药。然而,肠对 S-亚硝基硫醇的吸收(这是其血管生物利用度的第一个限制屏障)很少得到评估。本研究使用基于人细胞的肠屏障体外模型,旨在阐明肠内转运的机制(被动或主动、细胞旁或细胞内途径),并预测三种 S-亚硝基硫醇的吸收部位:S-亚硝基谷胱甘肽(GSNO)、S-亚硝基-N-乙酰-L-半胱氨酸(NACNO)和 S-亚硝基-N-乙酰-D-青霉胺(SNAP)。这些 S-亚硝基硫醇包含携带亚硝基基团的不同骨架,赋予它们不同的物理化学特性和生物学活性(抗氧化和抗炎)。根据表观渗透系数值,三种 S-亚硝基硫醇属于中等渗透性类别。双向表观渗透系数的评估表明三种 S-亚硝基硫醇均为被动扩散。GSNO 和 NACNO 优先通过细胞内途径穿过肠屏障,而 SNAP 则通过细胞内外途径都能穿过。最后,NACNO 的通透性在 pH6.4 时得到促进,这接近于肠空肠部分的 pH 值。通过这项研究,我们确定了 S-亚硝基硫醇的吸收机制,并推测它们可以通过口服途径给药。