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  Morphine Analogues: Relationship between Chemical Structure and Interaction with Proximal Tubular Transporters – Contraluminal Organic Cation and Anion Transporter, Luminal H+ /Organic Cation Exchanger, and Luminal Choline Transporter

Ullrich, K. J., & Rumrich, G. (1995). Morphine Analogues: Relationship between Chemical Structure and Interaction with Proximal Tubular Transporters – Contraluminal Organic Cation and Anion Transporter, Luminal H+ /Organic Cation Exchanger, and Luminal Choline Transporter. Cellular Physiology and Biochemistry, 5(4), 290-298. doi:10.1159/000154765.

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 Creators:
Ullrich, Karl Julius1, Author           
Rumrich, Gerhard1, Author           
Affiliations:
1Emeritusgroup Physiology, Max Planck Institute of Biophysics, Max Planck Society, ou_3273468              

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Free keywords: p-Aminohippurate transport; Codeine; N’-methylnicotinamide transport; Rat kidneys; Thebaine
 Abstract: In order to determine the role of different side groups in the interaction with different transporters, luminal and contraluminal stop-flow micro-perfusion was applied, and the apparent Ki values (mmol/l) of twelve morphine analogues were measured. Contraluminal organic cation transporter (Ki, cl, NMeN+; N’-methylnicotinamide): Those analogues which have an OH group on C atom 6 (normorphine, morphine, codeine, norcodeine) have higher KidNMeN+ values (0.64-0.87 mmol/l) than those compounds which have an·group on C atom 6 (noroxymorphone, oxycodone, hydrocodone, hydromorphone (0.14-0.24 mmol/l). Luminal H+/organic cation exchanger (Ki1, mpp+; methylphenylpyridinium): analogues with both a OCH3 group and a NCH3 group on C atoms 3 and 6, respectively, have higher Ki, 1mpp+ values than those where one or both CH3 groups were missing: codeine 5.1 → norcodeine 0.5 or morphine 1.15;hydrocodone 1.0 → hydromorphone 0.54; oxycodone 1.5 -→ noroxymorphone 0.63. The Ki, cl, NMeN+ and Ki, 1, Mpp+values of the 3β- and 6β-glucuronide conjugates of morphine were much higher ( > 10 mmol/l) than those of the other analogues. Luminal choline transporter (Ki, 1, choiine+): The tested analogues have Ki, 1, Choline+ values of between 6 and 25 mmol/l, except the glucuronide conjugates which do not inhibit at all. With the exception of the 14-OH compounds oxycodone and noroxymorphone, they show a similar inhibitory pattern as against the contraluminal NMeN+ transporter. Contraluminal organic anion transporter (Ki cl pah;p-aminohippurate): 8 out of the 12 morphine analogues have Ki, d, pah values of between 5.7 and 7.3 mmol/l. Only the Ki values of codeine and the diacetyl and glucuronide conjugates are somewhat lower (2.1-3.5 mmol). The latter have Ki values against the cation transporters which are much higher than that of all other morphine analogues. The data indicate that the morphine analogues are ‘polysubstrates’ that interact with different organic cation transporters and the organic anion transporter. These transporters are, therefore, rather unspecific. Furthermore, each transporter has his preference for certain side groups in the substrate molecules.

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Language(s): eng - English
 Dates: 1995-03-032008-09-041995
 Publication Status: Issued
 Pages: 9
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1159/000154765
 Degree: -

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Title: Cellular Physiology and Biochemistry
Source Genre: Journal
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Publ. Info: Basel : S. Karger
Pages: - Volume / Issue: 5 (4) Sequence Number: - Start / End Page: 290 - 298 Identifier: ISSN: 1015-8987
CoNE: https://pure.mpg.de/cone/journals/resource/954925585261