Structural modifications of the neomycin class of aminoglycosides

Bera, Smritilekha; Mondal, Dhananjoy; Palit, Subhadeep; Schweizer, Frank

doi:10.1039/c6md00079g

Cited by 18 publications

(15 citation statements)

References 151 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…AAGs were synthesized by modification of the AG’s primary amine or hydroxyl functions. Lipophilic groups were conjugated to the AG’s core of NEO 1 (NEO), NEA 6 , PARO 2 , PARA 7 , KANA 3 and KANB 4 , TOB 5 and nebramine 8 (NEB) ( Figure 1 ) using several strategies [ 3 , 4 , 5 , 6 , 7 , 8 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 ]. The amine functions of the selected AG were converted to alkyl- or aryl-amide(s) or to carbamates, leading to a decrease in the number of positive charges present at physiological pH.…”

Section: Antibacterial Amphiphilic Aminoglycosides (Antibacterial mentioning

confidence: 99%

“…At the end of the first part of this review article, other advances in the field of antibacterial AAGs, published since 2016 after the appearance of several review articles [ 7 , 8 , 30 , 31 , 32 ], are reviewed with an emphasis on AAGs made of an AG core conjugated to an adjuvant or an antibiotic drug of another class (antibiotic hybrids), as recently developed by Schweizer, Zhanel and coworkers.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Amphiphilic Aminoglycosides as Medicinal Agents

Dezanet

Kempf

Mingeot‐Leclercq

et al. 2020

IJMS

View full text Add to dashboard Cite

The conjugation of hydrophobic group(s) to the polycationic hydrophilic core of the antibiotic drugs aminoglycosides (AGs), targeting ribosomal RNA, has led to the development of amphiphilic aminoglycosides (AAGs). These drugs exhibit numerous biological effects, including good antibacterial effects against susceptible and multidrug-resistant bacteria due to the targeting of bacterial membranes. In the first part of this review, we summarize our work in identifying and developing broad-spectrum antibacterial AAGs that constitute a new class of antibiotic agents acting on bacterial membranes. The target-shift strongly improves antibiotic activity against bacterial strains that are resistant to the parent AG drugs and to antibiotic drugs of other classes, and renders the emergence of resistant Pseudomonas aeruginosa strains highly difficult. Structure–activity and structure–eukaryotic cytotoxicity relationships, specificity and barriers that need to be crossed in their development as antibacterial agents are delineated, with a focus on their targets in membranes, lipopolysaccharides (LPS) and cardiolipin (CL), and the corresponding mode of action against Gram-negative bacteria. At the end of the first part, we summarize the other recent advances in the field of antibacterial AAGs, mainly published since 2016, with an emphasis on the emerging AAGs which are made of an AG core conjugated to an adjuvant or an antibiotic drug of another class (antibiotic hybrids). In the second part, we briefly illustrate other biological and biochemical effects of AAGs, i.e., their antifungal activity, their use as delivery vehicles of nucleic acids, of short peptide (polyamide) nucleic acids (PNAs) and of drugs, as well as their ability to cleave DNA at abasic sites and to inhibit the functioning of connexin hemichannels. Finally, we discuss some aspects of structure–activity relationships in order to explain and improve the target selectivity of AAGs.

show abstract

Section: Antibacterial Amphiphilic Aminoglycosides (Antibacterial mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Amphiphilic Aminoglycosides as Medicinal Agents

Dezanet

Kempf

Mingeot‐Leclercq

et al. 2020

IJMS

View full text Add to dashboard Cite

show abstract

“…Along with the former strategies, other synthetic pathways relaying on multistep protection/functionalization/deprotection approaches have been developed. However, since the chemistry exploited for the synthesis of AG-based gene delivery vectors reviewed herein pertains to the strategies depicted in Figure 2, we will not go through these strategies, suggesting that interested readers refer to the comprehensive review cited in [9,10].…”

Section: Classification and Chemistry Of Aminoglycosides (Ags)mentioning

confidence: 99%

Aminoglycosides: From Antibiotics to Building Blocks for the Synthesis and Development of Gene Delivery Vehicles

Bellucci

Volonterio

2020

Antibiotics

View full text Add to dashboard Cite

Aminoglycosides are a class of naturally occurring and semi synthetic antibiotics that have been used for a long time in fighting bacterial infections. Due to acquired antibiotic resistance and inherent toxicity, aminoglycosides have experienced a decrease in interest over time. However, in the last decade, we are seeing a renaissance of aminoglycosides thanks to a better understanding of their chemistry and mode of action, which had led to new trends of application. The purpose of this comprehensive review is to highlight one of these new fields of application: the use of aminoglycosides as building blocks for the development of liposomal and polymeric vectors for gene delivery. The design, synthetic strategies, ability to condensate the genetic material, the efficiency in transfection, and cytotoxicity as well as when available, the antibacterial activity of aminoglycoside-based cationic lipids and polymers are covered and critically analyzed.

show abstract

“…It is assembling's in many types of drug preparations, for example, ointments, creams, and eye drops. Neomycin sulfate is mainly composed of mixture of NEO B and its stereoisomer NEO C (antimicrobial potency lower than that of B), as well as of small amounts of other constituents (A, D, E and F) which show no antimicrobial activity (Bera S et al, 2016;Mišić IR et al, 2015). It is widely used in the treatment of gram-negative bacterial infections like tuberculosis and severe hospital-acquired infections (Lewis JE et al, 1976;Guideline IH, 2005).…”

Section: Introductionmentioning

confidence: 99%

“…It is widely used in the treatment of gram-negative bacterial infections like tuberculosis and severe hospital-acquired infections (Lewis JE et al, 1976;Guideline IH, 2005). The official method for the assay of NEO in pharmaceuticals is microbiological techniques set up by the Food and Drug Administration (Bera S et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Spectrophotometric determination of neomycin sulphate in tablets form via reaction with ninhydrin reagent

Alsamarrai¹,

Al-Abbasi²,

Al-Samarrai³

2019

ijrps

View full text Add to dashboard Cite

A new, sensitive, simple and cheap spectrophotometric method for the determination of Neomycin Sulphate (NEO) in pharmaceutical forms has been developed. The method is based on the reaction between NEO and NIN in basic medium. The maximum absorbance was at 574 nm. The conditions affecting the reaction were optimized. Under the optimal conditions, the calibration curve was linear over the range of 0.0002-0.0011 mol/L. The limit of detection and limit of quantification were 5.423×10-6 mol/L, and 1.643×10-5 mol/L, RSD% of seven replicate was 0.8217- 0.8321% and Rec% was between 99.2168-100.8857%. The proposed method was successfully applied to the determination of NEO tablets form.

show abstract

Structural modifications of the neomycin class of aminoglycosides

Abstract: This review encompasses comprehensive literature on synthetic modification and biological activities of clinically used neomycin-class aminoglycoside antibiotics to alleviate dose-related toxicity and pathogenic resistance.

Cited by 18 publications

References 151 publications

Amphiphilic Aminoglycosides as Medicinal Agents

Amphiphilic Aminoglycosides as Medicinal Agents

Aminoglycosides: From Antibiotics to Building Blocks for the Synthesis and Development of Gene Delivery Vehicles

Spectrophotometric determination of neomycin sulphate in tablets form via reaction with ninhydrin reagent

Contact Info

Product

Resources

About