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Antibiotics
Volume 9
Issue 4
10.3390/antibiotics9040182
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Article

Selective Modification of Streptozotocin at the C3 Position to Improve Its Bioactivity as Antibiotic and Reduce Its Cytotoxicity towards Insulin-Producing β Cells

by
Ji Zhang
1,†,
Liubov Yakovlieva
1,†,
Bart J. de Haan
2,
Paul de Vos
2,
Adriaan J. Minnaard
1,
Martin D. Witte
1 and
Marthe T. C. Walvoort
1,*
1
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG Groningen, The Netherlands
2
Department of Pathology and Medical Biology, University of Groningen Medical Center, Hanzeplein 1, 9700 RB Groningen, The Netherlands
*
Author to whom correspondence should be addressed.
†
Authors contributed equally to the manuscript.
Antibiotics 2020, 9(4), 182; https://doi.org/10.3390/antibiotics9040182
Received: 13 March 2020 / Revised: 31 March 2020 / Accepted: 10 April 2020 / Published: 15 April 2020
(This article belongs to the Section Biosynthesis and Combinatorial Approaches in Antimicrobial Discovery)
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Abstract

With the increasing resistance of bacteria to current antibiotics, novel compounds are urgently needed to treat bacterial infections. Streptozotocin (STZ) is a natural product that has broad-spectrum antibiotic activity, albeit with limited use because of its toxicity to pancreatic β cells. In an attempt to derivatize STZ through structural modification at the C3 position, we performed the synthesis of three novel STZ analogues by making use of our recently developed regioselective oxidation protocol. Keto-STZ (2) shows the highest inhibition of bacterial growth (minimum inhibitory concentration (MIC) and viability assays), but is also the most cytotoxic compound. Pre-sensitizing the bacteria with GlcNAc increased the antimicrobial effect, but did not result in complete killing. Interestingly, allo-STZ (3) revealed moderate concentration-dependent antimicrobial activity and no cytotoxicity towards β cells, and deoxy-STZ (4) showed no activity at all. View Full-Text
Keywords: antibiotics; regioselective oxidation; streptozotocin; β cells antibiotics; regioselective oxidation; streptozotocin; β cells
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Zhang, J.; Yakovlieva, L.; de Haan, B.J.; de Vos, P.; Minnaard, A.J.; Witte, M.D.; Walvoort, M.T.C. Selective Modification of Streptozotocin at the C3 Position to Improve Its Bioactivity as Antibiotic and Reduce Its Cytotoxicity towards Insulin-Producing β Cells. Antibiotics 2020, 9, 182. https://doi.org/10.3390/antibiotics9040182

AMA Style

Zhang J, Yakovlieva L, de Haan BJ, de Vos P, Minnaard AJ, Witte MD, Walvoort MTC. Selective Modification of Streptozotocin at the C3 Position to Improve Its Bioactivity as Antibiotic and Reduce Its Cytotoxicity towards Insulin-Producing β Cells. Antibiotics. 2020; 9(4):182. https://doi.org/10.3390/antibiotics9040182

Chicago/Turabian Style

Zhang, Ji, Liubov Yakovlieva, Bart J. de Haan, Paul de Vos, Adriaan J. Minnaard, Martin D. Witte, and Marthe T. C. Walvoort. 2020. "Selective Modification of Streptozotocin at the C3 Position to Improve Its Bioactivity as Antibiotic and Reduce Its Cytotoxicity towards Insulin-Producing β Cells" Antibiotics 9, no. 4: 182. https://doi.org/10.3390/antibiotics9040182

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