Uptake and metabolism of fluorescent steroids by mycobacterial cells
Copyright © 2016 Elsevier Inc. All rights reserved..
Fluorescent steroids BODIPY-cholesterol (BPCh) and 7-nitrobenzoxadiazole-4-amino-(NBD)-labeled 22-NBD-chelesterol (22NC) as well as synthesized 20-(NBD)-pregn-5-en-3β-ol (20NP) were found to undergo bioconversions by Mycobacterium tuberculosis H37Rv and M. smegmatis mc2 155. The major fluorescent products were determined to be 4-en-3-one derivatives of the compounds. Degradation of NBD fluorophore was also detected in the cases of 22NC and 20NP, but neither NBD degradation nor steroidal part modification were observed for the synthesized 3-(NBD)-cholestane. Mycobacterial 3β-hydroxysteroid dehydrogenases were concluded to be responsible for the formation of the 4-en-3-one derivatives. All the compounds tested were found to cause staining both membrane lipids and cytosolic lipid droplets when incubated with mycobacteria in different manner, demonstrating ability of the steroids to reside in the compartments. The findings reveal a potential of the compounds for monitoring of steroid interactions with mycobacteria and provide information for design of new probes for this purpose.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2017 |
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| Erschienen: |
2017 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:117 |
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| Enthalten in: |
Steroids - 117(2017) vom: 08. Jan., Seite 29-37 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Faletrov, Yaroslav [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 30.08.2017 Date Revised 19.12.2017 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.steroids.2016.10.001 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2016 Elsevier Inc. All rights reserved. | ||
| 520 | |a Fluorescent steroids BODIPY-cholesterol (BPCh) and 7-nitrobenzoxadiazole-4-amino-(NBD)-labeled 22-NBD-chelesterol (22NC) as well as synthesized 20-(NBD)-pregn-5-en-3β-ol (20NP) were found to undergo bioconversions by Mycobacterium tuberculosis H37Rv and M. smegmatis mc2 155. The major fluorescent products were determined to be 4-en-3-one derivatives of the compounds. Degradation of NBD fluorophore was also detected in the cases of 22NC and 20NP, but neither NBD degradation nor steroidal part modification were observed for the synthesized 3-(NBD)-cholestane. Mycobacterial 3β-hydroxysteroid dehydrogenases were concluded to be responsible for the formation of the 4-en-3-one derivatives. All the compounds tested were found to cause staining both membrane lipids and cytosolic lipid droplets when incubated with mycobacteria in different manner, demonstrating ability of the steroids to reside in the compartments. The findings reveal a potential of the compounds for monitoring of steroid interactions with mycobacteria and provide information for design of new probes for this purpose | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a 22-NBD-cholesterol (PubChem CID: 127604) | |
| 650 | 4 | |a 3β-Hydroxysteroid dehydrogenase | |
| 650 | 4 | |a Fluorescence microscopy | |
| 650 | 4 | |a Fluorescent steroids | |
| 650 | 4 | |a Lipid droplets | |
| 650 | 4 | |a Mass-spectrometry | |
| 650 | 4 | |a Menadione sodium bisulfite (PubChem CID: 23665888) | |
| 650 | 4 | |a Mycobacteria | |
| 650 | 4 | |a Nile Red (PubChem CID: 65182) | |
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| 700 | 1 | |a Dziadek, Jarosław |e verfasserin |4 aut | |
| 700 | 1 | |a Rudaya, Elena |e verfasserin |4 aut | |
| 700 | 1 | |a Edimecheva, Irina |e verfasserin |4 aut | |
| 700 | 1 | |a Shkumatov, Vladimir |e verfasserin |4 aut | |
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