Author Type

Graduate Student

Date of Award

2008

Document Type

Dissertation

Publication Status

Version of Record

Submission Date

October 2026

Thesis/Dissertation Advisor [Chair]

Cudic, Predrag

Abstract

In this dissertation the synthesis, characterization, and binding properties of carbohydrate receptors 34-38 was described. Macrocyclic receptor 34 and macrobicyclic receptor 35 bind monosaccharides in aqueous media through combination of hydrophobic, electrostatic and hydrogen bonding interactions. The dissociation constants (Kd) for the complexes between 1 ,8-naphthyridine receptors 34, and 35 with a variety of neutral and negatively charged monosaccharides in aqueous media were determined by fluorimetric and UV /vis titration. The observed values are in the range from ~0.3 to >10 mM, within the Kd range reported for lectin/monosaccharide complexes. However, among monosaccharide substrates tested receptor 34 showed the strongest affinity for sialic acid (Kd = ~0 . 3 mM), a monosaccharide that plays many important roles in a wide variety of physiological and pathological processes. Macrocyclic receptor 34 recognizes not only sialic acid in solution, but also binds selectively in vitro to human cancer cell surface carbohydrate antigens containing terminal sialic acid moieties. In addition, besides their binding selectivity, receptors 34 and 35 display also the ability to discriminate between closely related monosaccharide substrates by opposite variation of the fluorescence emission intensity. Structure-binding relationship study of receptor 34 revealed that H-bonding donor/acceptor pattern and presence of positive charge on receptor's side arms are crucial for selective monosaccharide binding in aqueous media.

Extent

199 p.

Comments

Dissertation (Ph.D.)--Florida Atlantic University, 2008.|Dissertation (Ph.D.)--Florida Atlantic University, 2008.

Identifier

FA00000844

Format

pdf

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