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On guanidinium and cellular uptake.

Wexselblatt E, Esko JD, Tor Y - J. Org. Chem. (2014)

Bottom Line: Although impressive uptake has been demonstrated for nonoligomeric and nonpept(o)idic guanidinylated scaffolds in cell cultures and animal models, the fundamental understanding of these processes is lacking.Charge pairing and hydrogen bonding with cell surface counterparts have been proposed, but their exact role remains putative.The impact of the number and spatial relationships of the guanidinium groups on delivery and organelle/organ localization is yet to be established.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry and Biochemistry and ‡Department of Cellular and Molecular Medicine, University of California , San Diego 9500 Gilman Dr., La Jolla, California 92093, United States.

ABSTRACT
Guanidinium-rich scaffolds facilitate cellular translocation and delivery of bioactive cargos through biological barriers. Although impressive uptake has been demonstrated for nonoligomeric and nonpept(o)idic guanidinylated scaffolds in cell cultures and animal models, the fundamental understanding of these processes is lacking. Charge pairing and hydrogen bonding with cell surface counterparts have been proposed, but their exact role remains putative. The impact of the number and spatial relationships of the guanidinium groups on delivery and organelle/organ localization is yet to be established.

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Representative structuresof monosaccharide-based transporters:(a) glucose, (b) mannose, (c) allose, and (d) galactose.64
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fig10: Representative structuresof monosaccharide-based transporters:(a) glucose, (b) mannose, (c) allose, and (d) galactose.64

Mentions: Other scaffolds investigated byChung and co-workers include thedisaccharides lactose,61 sucrose,62 and trehalose (Figure 9),63 the monosaccharides glucose, mannose,allose, and galactose (Figure 10),64 and monomeric myo- and scyllo-inositols (Figure 11).65 Both the lactose- and sucrose-based transportersfeature seven guanidinium groups tethered to the sugar through linkersof different lengths (Figure 9a,b). For both,the intracellular localization was influenced by the length, or lipophilicity,of the linker and in the case of sucrose scaffold also by the natureof the fluorescent dye attached to the transporter.61,62


On guanidinium and cellular uptake.

Wexselblatt E, Esko JD, Tor Y - J. Org. Chem. (2014)

Representative structuresof monosaccharide-based transporters:(a) glucose, (b) mannose, (c) allose, and (d) galactose.64
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4120969&req=5

fig10: Representative structuresof monosaccharide-based transporters:(a) glucose, (b) mannose, (c) allose, and (d) galactose.64
Mentions: Other scaffolds investigated byChung and co-workers include thedisaccharides lactose,61 sucrose,62 and trehalose (Figure 9),63 the monosaccharides glucose, mannose,allose, and galactose (Figure 10),64 and monomeric myo- and scyllo-inositols (Figure 11).65 Both the lactose- and sucrose-based transportersfeature seven guanidinium groups tethered to the sugar through linkersof different lengths (Figure 9a,b). For both,the intracellular localization was influenced by the length, or lipophilicity,of the linker and in the case of sucrose scaffold also by the natureof the fluorescent dye attached to the transporter.61,62

Bottom Line: Although impressive uptake has been demonstrated for nonoligomeric and nonpept(o)idic guanidinylated scaffolds in cell cultures and animal models, the fundamental understanding of these processes is lacking.Charge pairing and hydrogen bonding with cell surface counterparts have been proposed, but their exact role remains putative.The impact of the number and spatial relationships of the guanidinium groups on delivery and organelle/organ localization is yet to be established.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry and Biochemistry and ‡Department of Cellular and Molecular Medicine, University of California , San Diego 9500 Gilman Dr., La Jolla, California 92093, United States.

ABSTRACT
Guanidinium-rich scaffolds facilitate cellular translocation and delivery of bioactive cargos through biological barriers. Although impressive uptake has been demonstrated for nonoligomeric and nonpept(o)idic guanidinylated scaffolds in cell cultures and animal models, the fundamental understanding of these processes is lacking. Charge pairing and hydrogen bonding with cell surface counterparts have been proposed, but their exact role remains putative. The impact of the number and spatial relationships of the guanidinium groups on delivery and organelle/organ localization is yet to be established.

Show MeSH