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HO HO HO O HO O OH OH HN O CH3 H H
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Sialic acid
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2 days to move to the region of the tips of the villi, where they are then shed into the lumen A schematic view of the surface of the epithelial cells shows a further 10 30-fold surface expansion [62,63,69] structures, in the form of microvilli on the luminal side of the cell layer, as shown in Fig 25 The villi and microvilli structures are found in highest density in the duodenum, jejunum, and ileum, and in lower density in a short section of the proximal colon [66] The microvilli have glycoproteins (the glycocalyx) protruding into the luminal uid There is residual negative charge in the glycoproteins Some cells in the monolayer are known as goblet cells (not shown in Figs 24 and 25), whose function is to produce the mucus layer that blankets the glycocalyx The mucus layer is composed of a high-molecular-weight (HMW) (2 106 Da) glycoprotein, which is 90% oligosaccharide, rich in sialic acid (Fig 26) residues, imparting negative charge to the layer [63] Studies of the diffusion of drug molecules through the mucus layer suggest that lipophilic molecules are slowed by it [72] The glycocalyx and the mucus layer make up the structure of the unstirred water layer (UWL) [73] The thickness of the UWL is estimated to be 30 100 mm in vivo, consistent with very ef cient stirring effects [74] In isolated tissue (in the absence of stirring), the mucus layer is 300 700 mm thick [73] The pH in the unstirred water layer is $52 62, and might be regulated independently of the luminal pH (Section 23) The mucus layer may play a role in regulating the epithelial cell surface pH [73] The membrane surface facing the lumen is called the apical surface, and the membrane surface on the side facing blood is called the basolateral surface The intestinal cells are joined at the tight junctions [63,75] These junctions have pores that can allow small molecules (MW < 200 Da) to diffuse through in aqueous solu tion In the jejunum, the pores are $7 9 A in size In the ileum the junctions are in size (ie, dimensions of mannitol) [63] tighter, and pores are $3 4 A The apical surface is loaded with more than 20 different digestive enzymes and proteins; the protein : lipid ratio is high: 17 : 1 [63] The half-life of these proteins is $6 12 h, whereas the epithelial cells last 2 3 days So the cell must replace these constituents without depolarizing itself The cytoskeleton may play a role
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Figure 27 Schematic of the apical phospholipid bilayer surface of the epithelial cells, indicating three types of passive diffusion: transcellular (1a!1b!1c), paracellular (2a!2b!2c), and the hypothesized lateral, under the skin of the tight junction (3a!3b!3c) modes Tight-junction matrix of proteins highly stylized, based on Ref 75 [Avdeef, A, Curr Topics Med Chem, 1, 277 351 (2001) Reproduced with permission from Bentham Science Publishers, Ltd]
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pH MICROCLIMATE
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in maintaining the polar distribution of the surface constituents [63] After a permeant passes through the cell barrier, it encounters a charge-selective barrier in the basement membrane (Fig 25) [76] Positively charged drugs have a slightly higher permeability through it After this barrier, drug molecules may enter the blood capillary network through openings in the highly fenestrated capillaries Epithelial cell surfaces are composed of bilayers made with phospholipids, as shown in the highly stylized drawing in Fig 27 Two principal routes of passive diffusion are recognized: transcellular (1a ! 1b ! 1c in Fig 27) and paracellular (2a ! 2b ! 2c) Lateral exchange of phospholipid components of the inner lea et of the epithelial bilayer seems possible, mixing simple lipids between the apical and basolateral side However, whether the membrane lipids in the outer lea et can diffuse across the tight junction is a point of controversy, and there may be some evidence in favor of it (for some lipids) [63] In this book, a third passive mechanism, based on lateral diffusion of drug molecules in the outer lea et of the bilayer (3a ! 3b ! 3c), will be hypothesized as a possible mode of transport for polar or charged amphiphilic molecules In the transport across a phospholipid bilayer by passive diffusion, the permeability of the neutral form of a molecule is $108 times greater than that of the charged form For the epithelium, the discrimination factor is 105 The basement membrane (Fig 25) allows passage of uncharged molecules more readily than charged species by a factor of 10 [76]
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