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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 dimeric (a) myo-inositoland (b) scyllo-inositol.54
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fig7: Representative structuresof dimeric (a) myo-inositoland (b) scyllo-inositol.54

Mentions: Searching for naturally occurring scaffolds,Chung and co-workersfocused on carbohydrates as polyfunctional cores for molecular transporters.The intracellular localization of myo- and scyllo-inositol dimers bearing eight guanidinium groupsdiffered from that of the Tat and (Arg)8 peptides, suggestinga distinct clathrin-independent internalization pathway (Figure 7).54 Unlike Tat peptides,these compounds were found mainly along the heart, lung and braintissues, displaying unique distribution both in vitro and in vivo.In addition, conjugation of doxorubicin to one of the transporterssignificantly increased drug uptake and its intracellular permeationin brain tissues.54


On guanidinium and cellular uptake.

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

Representative structuresof dimeric (a) myo-inositoland (b) scyllo-inositol.54
© Copyright Policy
Related In: Results  -  Collection

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

fig7: Representative structuresof dimeric (a) myo-inositoland (b) scyllo-inositol.54
Mentions: Searching for naturally occurring scaffolds,Chung and co-workersfocused on carbohydrates as polyfunctional cores for molecular transporters.The intracellular localization of myo- and scyllo-inositol dimers bearing eight guanidinium groupsdiffered from that of the Tat and (Arg)8 peptides, suggestinga distinct clathrin-independent internalization pathway (Figure 7).54 Unlike Tat peptides,these compounds were found mainly along the heart, lung and braintissues, displaying unique distribution both in vitro and in vivo.In addition, conjugation of doxorubicin to one of the transporterssignificantly increased drug uptake and its intracellular permeationin brain tissues.54

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