id:"swepub:oai:DiVA.org:uu-17658"
Sökning: id:"swepub:oai:DiVA.org:uu-17658" > Structural evaluati...
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| Fältnamn | Indikatorer | Metadata |
|---|---|---|
| 000 | 03445naa a2200325 4500 | |
| 001 | oai:DiVA.org:uu-17658 | |
| 003 | SwePub | |
| 008 | 080806s2008 | |||||||||||000 ||eng| | |
| 024 | 7 | a https://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-176582 URI |
| 024 | 7 | a https://doi.org/10.1002/rcm.36672 DOI |
| 040 | a (SwePub)uu | |
| 041 | a engb eng | |
| 042 | 9 SwePub | |
| 072 | 7 | a ref2 swepub-contenttype |
| 072 | 7 | a art2 swepub-publicationtype |
| 100 | 1 | a Lampinen Salomonsson, Matildau Uppsala universitet,Avdelningen för analytisk farmaceutisk kemi4 aut |
| 245 | 1 0 | a Structural evaluation of the glucuronides of morphine and formoterol using chemical derivatization with 1,2-dimethylimidazole-4-sulfonyl chloride and liquid chromatography/ion trap mass spectrometry |
| 264 | 1 | b Wiley,c 2008 |
| 338 | a print2 rdacarrier | |
| 520 | a For the first time chemical derivatization of isomeric drug glucuronides with 1,2-dimethylimidazole-4-sulfonyl chloride (DMISC) has been successfully applied as a tool for determining the site of conjugation. This provides a way to differentiate between glucuronide isomers containing aliphatic and phenolic hydroxyl groups. The analyses were performed with liquid chromatography/electrospray ion trap mass spectrometry (LC/ESI-MSn). DMISC has previously been shown to react selectively with phenols in estrogens, thus improving sensitivity in ESI-MS. The model compounds selected for this study were commercially available standards of formoterol, morphine, morphine-3-glucuronide (M3G), and morphine-6-glucuronide (M6G). Formoterol glucuronides were produced with an enzymatic method in house. Both formoterol and morphine possess one phenolic and one aliphatic hydroxyl group where glucuronidation could take place. The product ion mass spectra of the native morphine glucuronides were indistinguishable due to the initial neutral loss of monodehydrated glucuronic acid (1.76u). However, a significant difference between the isomers was observed with DMISC derivatization, as only the form with a free phenol, M6G, gave a detectable reaction product. Formoterol formed two detectable glucuronide isomers in the enzymatic reaction. Their respective sites of conjugation could not be directly determined from the product ion spectra. Reaction with DMISC, however, gave a detectable product with only one of the isomers. Based on previous experience of the preferred DMISC reactions with phenols, and interpretation of the fragmentation pattern of the derivative, it was concluded that the reactive isomer had a free phenol, and was thus conjugated on the aliphatic chain. | |
| 650 | 7 | a NATURVETENSKAPx Kemix Fysikalisk kemi0 (SwePub)104022 hsv//swe |
| 650 | 7 | a NATURAL SCIENCESx Chemical Sciencesx Physical Chemistry0 (SwePub)104022 hsv//eng |
| 653 | a Spectroscopy | |
| 653 | a Spektroskopi | |
| 700 | 1 | a Bondesson, Ulfu Uppsala universitet,Avdelningen för analytisk farmaceutisk kemi4 aut0 (Swepub:uu)ulfbonde |
| 700 | 1 | a Hedeland, Mikaelu Uppsala universitet,Avdelningen för analytisk farmaceutisk kemi4 aut0 (Swepub:uu)mikahede |
| 710 | 2 | a Uppsala universitetb Avdelningen för analytisk farmaceutisk kemi4 org |
| 773 | 0 | t Rapid Communications in Mass Spectrometryd : Wileyg 22:17, s. 2685-2697q 22:17<2685-2697x 0951-4198x 1097-0231 |
| 856 | 4 8 | u https://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-17658 |
| 856 | 4 8 | u https://doi.org/10.1002/rcm.3667 |
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