ArticlePharmaceutical research1999
Structural requirements for alkylglycoside-type renal targeting vector.
Article in Pharmaceutical research, 1999. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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Who cites it
2 citing papers in PubMed, 9 citations in OpenAlex.
- Thioglycosides as inhibitors of hSGLT1 and hSGLT2: potential therapeutic agents for the control of hyperglycemia in diabetes.International journal of medical sciences · 2007Article
- Detection of the membrane protein recognized by the kidney-specific alkylglucoside vector.Pharmaceutical research · 2000Article
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
purposeWe have previously shown Glc-S-C7-Me (octyl beta-D-thioglucoside) exhibits renal targeting potential in vivo in addition to its specific binding to the renal membrane fraction in vitro. Thus, "alkylglycoside" is considered to be a novel targeting vector for the kidney (1,2). The present study is designed to clarify the structural requirements for alkylglycoside as a renal targeting vector.
methodsInhibitory effects of various sugars and glycosides on 3H-Glc-S-C7-Me binding to the kidney membrane fraction were evaluated by a centrifugation method.
resultsAs far as the sugar moiety is concerned, no other sugars except D-aldohexose and D-aldohexose derivatives (containing F, S, and N) showed greater inhibition than D-glucose. Therefore, octylthio derivatives of various D-aldohexose were prepared and their inhibitory effects were investigated. The following findings were obtained: Equatorial OH at 4 position is essential; OH at 2 position can have either orientation or be deleted. As far as the alkyl moiety is concerned, the length, branching and electrical environment in the region of the glycoside bond are important; aromatic structures can substitute for the alkyl portion; the preferred glycoside bonding atom is as follows: S > NH > O.
conclusionsThe structural requirements for the renal targeting vector have been identified to be as follows: a hydrophobic group (alkyl chain or aromatic ring) should be introduced to a sugar (D-glucose, D-mannose, or 2-deoxy-D-glucose) via a beta-glycoside binding atom (S > NH > O).
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