Macrolactonolides: A novel class of anti-inflammatory compounds

Tomašković, Linda; Komac, Marijana; Stegić, Oresta Makaruha; Munić, Vesna; Ralić, Jovica; Stanić, Barbara; Banjanac, Mihailo; Marković, Stribor; Hrvačić, Boška; Paljetak, Hana Čipčić; Padovan, Jasna; Glojnarić, Ines; Haber, Vesna Eraković; Mesić, Milan; Merćep, Mladen

doi:10.1016/j.bmc.2012.10.036

Cited by 11 publications

(7 citation statements)

References 23 publications

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“…40 Development of macrolides without antibiotic properties is an active ield of research, and the inhalation of which could enable direct targeting of the airways, limiting undesirable systemic efects. [56][57][58][59] Of note, only limited gastrointestinal events were observed in this experiment, as previously described with azithromycin administration in adult horses. 23 However, enterocolitis susceptibility might vary depending on geographical areas.…”

Section: Discussionsupporting

confidence: 55%

“…Indeed, development of resistance has been reported with the long‐term use of azithromycin in chronic lung diseases in some studies, 55 but not in others 40 . Development of macrolides without antibiotic properties is an active field of research, and the inhalation of which could enable direct targeting of the airways, limiting undesirable systemic effects 56–59 . Of note, only limited gastrointestinal events were observed in this experiment, as previously described with azithromycin administration in adult horses 23 .…”

Section: Discussionmentioning

confidence: 50%

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Randomised study of the immunomodulatory effects of azithromycin in severely asthmatic horses

Mainguy-Seers

Vargas

Labrecque³

et al. 2019

Veterinary Record

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Neutrophilic inflammation is believed to contribute to the airway obstruction and remodelling in equine asthma. Azithromycin, an antibiotic with immunomodulatory properties, reduces pulmonary neutrophilia and hyper-responsiveness in human asthmatics and decreases airway remodelling in rodent models of asthma. It was therefore hypothesised that azithromycin would improve lung function, mucus accumulation and central airway remodelling by decreasing luminal neutrophilia in severe equine asthma. The effects of a 10-day treatment with either azithromycin or ceftiofur, an antimicrobial without immune-modulating activity, were assessed using a blind, randomised, crossover design with six severe asthmatic horses in clinical exacerbation. Lung function, tracheal mucus accumulation, tracheal wash bacteriology, bronchial remodelling, airway neutrophilia and mRNA expression of proinflammatory cytokines (interleukin (IL)-8, IL-17A, IL-1β, tumour necrosis factor-α) in bronchoalveolar lavage fluid were evaluated. Azithromycin decreased the expression of IL-8 (P=0.03, one-tailed) and IL-1β (P=0.047, one-tailed) but failed to improve the other variables evaluated. Ceftiofur had no effect on any parameter. The reduction of neutrophilic chemoattractants (IL-8, IL-1β) justifies further efforts to investigate the effects of a prolonged treatment with macrolides on airway neutrophilia and remodelling. The lack of efficacy of ceftiofur suggests that severe equine asthma should not be treated with antibiotics at first-line therapy.

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Section: Discussionsupporting

confidence: 55%

Section: Discussionmentioning

confidence: 50%

Randomised study of the immunomodulatory effects of azithromycin in severely asthmatic horses

Mainguy-Seers

Vargas

Labrecque³

et al. 2019

Veterinary Record

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“…For several decades now, our continuing primary interest lay in 14-membered macrolides and their semi-synthetic 15-membered derivatives targeting therapeutic areas of bacterial [ 32 – 34 ] and parasitic [ 35 ] infections, as well as inflammation [ 36 – 38 ]. In the search for novel scaffolds to be used as a fresh starting point for further derivatisation [ 39 ], we explored modifications to the macrocyclic ring.…”

Section: Resultsmentioning

confidence: 99%

Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A

Čikoš

Ćaleta

Žiher

et al. 2015

Beilstein J. Org. Chem.

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SummaryThree novel spiroketals were prepared by a one-pot transformation of 6-O-methyl-9(E)-hydroxyiminoerythronolide A. We present the formation of a [4.5]spiroketal moiety within the macrolide lactone ring, but also the unexpected formation of a 10-C=11-C double bond and spontaneous change of stereochemistry at position 8-C. As a result, a thermodynamically stable structure was obtained. The structures of two new diastereomeric, unsaturated spiroketals, their configurations and conformations, were determined by means of NMR spectroscopy and molecular modelling. The reaction kinetics and mechanistic aspects of this transformation are discussed. These rearrangements provide a facile synthesis of novel macrolide scaffolds.

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“…Многие из этих соединений, также называемых иммунолидами, были предложены в качестве потенциальных эффективных средств лечения заболеваний, сопровождающихся повышением количества нейтрофилов, включая ХОБЛ, бронхоэктатическую болезнь, облитерирующий бронхиолит и муковисцидоз [23]. Другая группа соединений, макролактониды (конъюгаты кортикостероида с макролидом), первоначально названные стеролидами, были синтезированы для аэрозольного применения при бронхиальной астме, но не получили распространения в клинической практике [24].…”

Section: разработка неантибактериальных макролидовunclassified

“…В данном обзоре мы изучим неантибактериальные эффекты макролидов, механизмы их реализации и перспективы клинического применения. Кроме того, мы коротко остановимся на попытках разработки новых противовоспалительных макролидов, лишенных антибактериального действия, которые получили название иммунолидов [12,23], а также конъюгат «кортикостероид-макролид», названных в одной публикации стеролидами [24].…”

Section: Introductionunclassified

Non-antimicrobial effects of macrolides: literature review

Skryabina¹,

Nikiforov²,

Shakhmardanov³

et al. 2021

Immunopathol Allergol Infectol

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The aim of this work is to review current publications on the non-antibacterial effects of macrolides. Macrolides are among the most widely prescribed broad-spectrum antibacterial drugs, especially in patients with respiratory infections. It is now recognized that drugs of this group, in particular azithromycin, also have an immunomodulatory effect, which leads to their therapeutic effect not only in infectious but in other chronic inflammatory diseases also. However, the frequent and prolonged use of macrolides in the treatment of respiratory tract diseases, and recently azithromycin in the treatment of COVID-19, has led to an increase in bacterial resistance to antibiotics of this group. Results: it was shown that one of the key aspects of the development of chronic inflammation of the respiratory tract (for instance, chronic obstructive pulmonary disease) is the loss of the protective epithelial barrier due to the effects of pathogens and pollutants. Azithromycin has been shown to enhance the barrier properties of airway epithelial cells over time, which makes an important contribution to its therapeutic effectiveness. The main non-antibacterial effects of macrolides are considered, which in the future can be applied in treatment of inflammatory diseases associated with airway epithelium damage.

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Macrolactonolides: A novel class of anti-inflammatory compounds

Cited by 11 publications

References 23 publications

Randomised study of the immunomodulatory effects of azithromycin in severely asthmatic horses

Randomised study of the immunomodulatory effects of azithromycin in severely asthmatic horses

Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A

Non-antimicrobial effects of macrolides: literature review

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