Abstract
Herein, we report the design and synthesis of the novel 12-membered non-antibiotic macrolide (8R,9S)-8,9-dihydro-6,9-epoxy-8,9- anhydropseudoerythromycin A (EM900), which was found to be a potent anti-inflammatory and/or immunomodulatory agent, capable of promoting monocyte to macrophage differentiation. This molecule shows improved acid stability, does not exhibit any anti-bacterial activity and has relatively low cytotoxicity against THP-1 cells. In addition, one of its analogues, (8R,9S)-4″,13-O- diacetyl-8,9-dihydro-6,9-epoxy-8,9-anhydropseudoerythromycin A (EM911), was found to be twice as effective as EM900.
Original language | English |
---|---|
Pages (from-to) | 3373-3376 |
Number of pages | 4 |
Journal | Bioorganic and Medicinal Chemistry Letters |
Volume | 21 |
Issue number | 11 |
DOIs | |
Publication status | Published - 2011 Jun 1 |
Externally published | Yes |
Keywords
- (8R,9S)-8,9-Dihydro-6,9-epoxy-8,9-anhydropseudoerythromycin A (EM900)
- 14-Membered non-antibiotic macrolide
- Anti-inflammatory agent
- Diffuse panbronchiolitis
- Immunomodulatory agent
ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry