Effect of Structural Modifications on the Biological Properties of Aminoglycoside Antibiotics Containing 2-Deoxystreptamine

Price, K. E.; Godfrey, John C.

doi:10.1016/s0065-2164(08)70572-0

Cited by 69 publications

(37 citation statements)

References 166 publications

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“…Aminoglycoside antibiotics are best known for inhibiting protein synthesis and for causing mistranslation on prokaryotic ribosomes (Price et al, 1977). Neomycin is also known to bind phosphoinositides (Schacht, 1976;Gabev et al, 1989) and intercede in biochemical and physiological processes that involve phosphoinositide metabolism.…”

Section: Antibiotics Interact With Coatomermentioning

confidence: 99%

Interaction of Coatomer with Aminoglycoside Antibiotics: Evidence That Coatomer Has at Least Two Dilysine Binding Sites

Hudson

Draper

1997

MBoC

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Coatomer is the soluble precursor of the COPI coat (coat protein I) involved in traffic among membranes of the endoplasmic reticulum and the Golgi apparatus. We report herein that neomycin precipitates coatomer from cell extracts and from purified coatomer preparations. Precipitation first increased and then decreased as the neomycin concentration increased, analogous to the precipitation of a polyvalent antigen by divalent antibodies. This suggested that neomycin cross-linked coatomer into large aggregates and implies that coatomer has two or more binding sites for neomycin. A variety of other aminoglycoside antibiotics precipitated coatomer, or if they did not precipitate, they interfered with the ability of neomycin to precipitate. Coatomer is known to interact with a motif (KKXX) containing adjacent lysine residues at the carboxyl terminus of the cytoplasmic domains of some membrane proteins resident in the endoplasmic reticulum. All of the antibiotics that interacted with coatomer contain at least two close amino groups, suggesting that the antibiotics might be interacting with the di-lysine binding site of coatomer. Consistent with this idea, di-lysine itself blocked the interaction of antibiotics with coatomer. Moreover, di-lysine and antibiotics each blocked the coating of Golgi membranes by coatomer. These data suggest that certain aminoglycoside antibiotics interact with di-lysine binding sites on coatomer and that coatomer contains at least two of these di-lysine binding sites.

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Section: Antibiotics Interact With Coatomermentioning

confidence: 99%

Interaction of Coatomer with Aminoglycoside Antibiotics: Evidence That Coatomer Has at Least Two Dilysine Binding Sites

Hudson

Draper

1997

MBoC

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“…The neomycins (3,4), paromomycins (5,6), and lividomycin B (7) are closely related antibiotics. Neomycin was the first antibiotic of this group tobe discovered.…”

Section: Ho Ohmentioning

confidence: 99%

“…Since several excellent reviews (Refs. [3][4][5][6] of the chemistry of aminoglycoside antibiotics have recently appeared, I will emphasise our recent advances.…”

mentioning

confidence: 99%

Recent advances in the synthesis of aminoglycoside antibiotics

Umezawa¹

1978

Pure and Applied Chemistry

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Abstract-Aminoglycoside antibiotics have established an important position in medicine and synthetic chemistry in this field has recently been developed. A review is provided of general synthetic schemes which we have developed for the total synthesis of streptomycin, dihydrostreptomycin, kanamycins, butirosin B, neomycin C, and others. Resistent bacteria are a serious subject in present chemotherapy and, the mechanisms of resistance have recently been revealed by medical microbiologists. ln the light of these mechanisms, an effort has been made to synthesise compounds, active against resistent bqcteria, by extension of the above mentioned synthetic schemes and by derivation from natural antibiotics.

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“…The paromamine analogue (2) and the neamine derivatives (3)(4)(5) were prepared from the trans-4-aminocyclohexanols (6, 10 and 11). These compounds have the 3-amino and 5-and 6-hydroxyl groups of the 2-deoxystreptamine ring replaced by hydrogen.…”

mentioning

confidence: 99%

Aminoglycosides. V. Synthesis of glucopyranoside derivatives of neamine modified in the 2-deoxystreptamine ring.

Pfeiffer¹,

Ku²,

Peterson

1981

J. Antibiot.

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Effect of Structural Modifications on the Biological Properties of Aminoglycoside Antibiotics Containing 2-Deoxystreptamine

Cited by 69 publications

References 166 publications

Interaction of Coatomer with Aminoglycoside Antibiotics: Evidence That Coatomer Has at Least Two Dilysine Binding Sites

Interaction of Coatomer with Aminoglycoside Antibiotics: Evidence That Coatomer Has at Least Two Dilysine Binding Sites

Recent advances in the synthesis of aminoglycoside antibiotics

Aminoglycosides. V. Synthesis of glucopyranoside derivatives of neamine modified in the 2-deoxystreptamine ring.

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