2-Deoxystreptamine Conjugates by Truncation–Derivatization of Neomycin

doi:10.3390/ph3030679

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Pharmaceuticals 2010, 3(3), 679-701; doi:10.3390/ph3030679

Article

2-Deoxystreptamine Conjugates by Truncation–Derivatization of Neomycin

M. Waqar Aslam¹, Leandro C. Tabares², Alessio Andreoni², Gerard W. Canters², Floris P.J.T. Rutjes¹ and Floris L. Van Delft^1,*

¹ Radboud University Nijmegen, IMM Organic Chemistry, Heyendaalseweg 135, 6525 AJ, Nijmegen, the Netherlands ² Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2300 RA, Leiden, the Netherlands

* Author to whom correspondence should be addressed.

Received: 18 December 2009; in revised form: 8 March 2010 / Accepted: 10 March 2010 / Published: 15 March 2010

(This article belongs to the Special Issue Antibiotics)

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Abstract: A small library of truncated neomycin-conjugates is prepared by consecutive removal of 2,6-diaminoglucose rings, oxidation-reductive amination of ribose, oxidation-conjugation of aminopyridine/aminoquinoline and finally dimerization. The dimeric conjugates were evaluated for antibacterial activity with a unique hemocyanin-based biosensor. Based on the outcome of these results, a second-generation set of monomeric conjugates was prepared and found to display significant antibacterial activity, in particular with respect to kanamycin-resistant E. coli.

Keywords: aminoglycosides; morpholine; aminopyridine; aminoquinoline; hemocyanin; biosensor; fluorescence

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Cite This Article

MDPI and ACS Style

Aslam, M.W.; Tabares, L.C.; Andreoni, A.; Canters, G.W.; Rutjes, F.P.; Van Delft, F.L. 2-Deoxystreptamine Conjugates by Truncation–Derivatization of Neomycin. Pharmaceuticals 2010, 3, 679-701.

AMA Style

Aslam MW, Tabares LC, Andreoni A, Canters GW, Rutjes FP, Van Delft FL. 2-Deoxystreptamine Conjugates by Truncation–Derivatization of Neomycin. Pharmaceuticals. 2010; 3(3):679-701.

Chicago/Turabian Style

Aslam, M. Waqar; Tabares, Leandro C.; Andreoni, Alessio; Canters, Gerard W.; Rutjes, Floris P.J.T.; Van Delft, Floris L. 2010. "2-Deoxystreptamine Conjugates by Truncation–Derivatization of Neomycin." Pharmaceuticals 3, no. 3: 679-701.

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