Cellular uptake of aminoglycosides, guanidinoglycosides, and poly-arginine

Journal of the American Chemical Society

Volumn 125, Issue 41, 2003, Pages 12374-12375

  Luedtke, Nathan W ^a,b   Carmichael, Peter ^a   Tor, Yitzhak ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINOGLYCOSIDE ANTIBIOTIC AGENT; BOVINE SERUM ALBUMIN; ETHYLENEDIAMINE; FLUORESCENT DYE; FRAMYCETIN; GLYCOSIDE; GUANIDINE; GUANIDINE DERIVATIVE; GUANIDINOGLYCOSIDE DERIVATIVE; NATURAL PRODUCT; NUCLEIC ACID; PEPTIDE DERIVATIVE; POLYAMINE; POLYARGININE; POLYCATION; TOBRAMYCIN; TRYPSIN; UNCLASSIFIED DRUG;

ADSORPTION; ANIMAL CELL; ANIMAL CELL CULTURE; ARTICLE; BINDING AFFINITY; BIOAVAILABILITY; CELL MEMBRANE TRANSPORT; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONJUGATION; CONTROLLED STUDY; CULTURE MEDIUM; DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG UPTAKE; ELECTRIC POTENTIAL; EUKARYOTE; FLUORESCENCE ACTIVATED CELL SORTING; FLUORESCENCE MICROSCOPY; INTERNALIZATION; MOLECULAR SIZE; NONHUMAN; QUANTUM MECHANICS; TRANSPORT KINETICS;

AMINOGLYCOSIDES; BORON COMPOUNDS; FLOW CYTOMETRY; GLYCOSIDES; GUANIDINE; HELA CELLS; HUMANS; MICROSCOPY, FLUORESCENCE; PEPTIDES;

EID: 0141954275     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0360135     Document Type: Article

References (24)

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13. See Supporting Information for experimental details.
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21. Treatment of guanidinoglycoside-containing cells with propidium iodide (a common viability test) indicates that the cells used for these experiments have intact membranes.
22. Microscopy experiments suggest that trypsin-mediated cleavage prior to FACS analysis does not affect the cellular localization, or the relative uptake efficiencies of these compounds (Figure 3 and Figure S1).
23. Previous studies have shown that peptidomimetics based upon neomycin-arginine conjugates also show efficient cellular uptake. This type of modification doubles the total number of basic groups and results in compounds possessing an equal number of amide, amine, and guanidine functionalities. The results presented here represent a direct comparison of purely amino-versus guanidino-containing glycosides.
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