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Once in the gastrointestinal tract, chemicals that have undergone conjugation reactions in the liver may be subject to the action of hydrolytic enzymes that de-conjugate the molecule. De-conjugation results in increased lipophilicity of the molecule and renders them once again subject to passive uptake. Re-absorbed chemicals enter the circulation via the hepatic portal vein, which shunts the chemical back to the liver where
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Figure 10.4 Enterohepatic circulation (as indicated by ). Polar xenobiotic conjugates are secreted into the intestine via the bile duct and gall bladder. Conjugates are hydrolyzed in the intestines, released xenobiotics are reabsorbed, and transported back to the liver via the portal vein.
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the chemical can be reprocessed (i.e., biotransformed) and eliminated. This process is called entero-hepatic circulation (Figure 10.4). A chemical may undergo several cycles of entero-hepatic circulation resulting in a signi cant increase in the retention time for the chemical in the body and increased toxicity. The liver functions to collect chemicals and other wastes from the body. Accordingly, high levels of chemicals may be attained in the liver, resulting in toxicity to this organ. Biotransformation of chemicals that occur in the liver sometimes results in the generation of reactive compounds that are more toxic than the parent compound resulting in damage to the liver. Chemical toxicity to the liver is discussed elsewhere ( 14).
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10.4.2 Active Transporters of the Bile Canaliculus
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The bile canaliculus constitutes only about 13% of the contiguous surface membrane of the hepatocyte but must function in the ef cient transfer of chemical from the hepatocyte to the bile duct. Active transport proteins located on the canalicular membrane are responsible for the ef cient shuttling of chemicals across this membrane. These active transporters are members of a multi-gene superfamily of proteins known as the ATP-binding cassette transporters. Two subfamilies are currently recognized as having major roles in the hepatic elimination of xenobiotics, as well as endogenous materials. The P-glycoprotein (ABC B) subfamily is responsible for the elimination of a variety of structurally diverse compounds. P-glycoprotein substrates typically have one or more cyclic structures, a molecular weight of 400 or greater, moderate to low lipophilicity (log Kow < 2), and high hydrogen (donor)-bonding potential. Parent xenobiotics that meet these criteria and hydroxylated derivatives of more lipophilic compounds are typically transported by P-glycoproteins. The multidrug-resistance associated protein (ABC C) subfamily of proteins largely recognizes anionic chemicals. ABC C substrates are commonly conjugates of xenobiotics (i.e., glutathione, glucuronic acid, and sulfate conjugates). Thus conjugation
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not only restricts passive diffusion of a lipophilic chemical but actually targets the xenobiotic for active transport across the canalicular membrane.
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The lungs are highly specialized organs that function in the uptake and elimination of volatile materials (i.e., gasses). Accordingly, the lungs can serve as a primary site for the elimination of chemicals that have a high vapor pressure. The functional unit of the lung is the alveolus. These small, highly vascularized, membraneous sacs serve to exchange oxygen from the air to the blood (uptake), and conversely, exchange carbon dioxide from the blood to the air (elimination). This exchange occurs through passive diffusion. Chemicals that are suf ciently volatile also may diffuse across the alveolar membrane, resulting in removal of the chemical from the blood and elimination into the air.
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Many processes function coordinately to ensure that chemicals distributed throughout the body are ef ciently eliminated at distinct and highly specialized locations. This unidirectional transfer of chemicals from the site of origin (storage, toxicity, etc.) to the site of elimination is a form of vectorial transport (Figure 10.5). The coordinate action of blood binding proteins, active transport proteins, blood ltration units, intracellular binding proteins, and biotransformation enzymes ensures the unidirectional ow of chemicals, ultimately resulting in their elimination. The evolution of this complex interplay of processes results in the ef cient clearance of toxicants and has provided the way for the co-evolution of complexity in form from unicellular to multi-organ organisms.
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