Background: This paper describes the synthesis of three different subfamilies of cyclic imides: methylphtalimides, carboxyl acid phtalimides and itaconimides.
Methods: Fifteen compounds (five of each sub-family) were obtained by the reaction of appropriated anhydrides and different aromatic amines, using the manual Topliss method. Their structures were confirmed by spectral data (IR and NMR). The antifungal activity of the synthesized compounds was investigated by broth microdilution to determine the minimal inhibitory concentration (MIC). The ability to inhibit the biofilm formation or destroy mature Candida albicans biofilm was also evaluated for the most active substances.
Results: The results indicated that only the itaconimides 11-15 exhibited potent and promising antifungal properties, with MIC100 between 1 and 64 μg mL-1, being several times more potent than the reference drug, Fluconazole. Compounds 11-15 inhibited between 64% and 95% of biofilm formation, and destroyed between 78% and 99% of mature biofilm at a concentration of 64 μg mL-1. ADME (absorption, distribution, metabolism and excretion) in silico evaluations were carried out to predict whether the molecules under study are good drug candidates.
Conclusions: Itaconimides appear to be promising and relevant as tools for the future development of new and effective medicinal agents to treat fungal diseases.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.2174/1573406412666160229150833 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Genesis and regulation of C-terminal cyclic imides from protein damage.
Proc Natl Acad Sci U S A
January 2025
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138.
C-Terminal cyclic imides are posttranslational modifications that can arise from spontaneous intramolecular cleavage of asparagine or glutamine residues resulting in a form of irreversible protein damage. These protein damage events are recognized and removed by the E3 ligase substrate adapter cereblon (CRBN), indicating that these aging-related modifications may require cellular quality control mechanisms to prevent deleterious effects. However, the factors that determine protein or peptide susceptibility to C-terminal cyclic imide formation or their effect on protein stability have not been explored in detail.
View Article and Find Full Text PDFOptimizing Surface Maleimide/cRGD Ratios Enhances Targeting Efficiency of cRGD-Functionalized Nanomedicines.
J Am Chem Soc
January 2025
Department of Pharmacy, The First Affiliated Hospital of University of Science and Technology of China (USTC), Laboratory of Precision and Intelligent Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei 230026, Anhui Province, China.
Thiol-maleimide (MI) chemistry is a cornerstone of bioconjugation strategies, particularly in the development of drug delivery systems. The cyclic arginine-glycine-aspartic acid (cRGD) peptide, recognized for its ability to target the integrin αβ, is commonly employed to functionalize maleimide-bearing nanoparticles (NPs) for fabricating cRGD-functionalized nanomedicines. However, the impact of cRGD density on tumor targeting efficiency remains poorly understood.
View Article and Find Full Text PDFSolvation layer effects on lithium migration in localized High-Concentration Electrolytes: Analyzing the diverse antisolvent Contributions.
J Colloid Interface Sci
April 2025
Multiscale Computational Materials Facility & Materials Genome Institute, School of Materials Science and Engineering, Fuzhou University, Fuzhou 350108, PR China. Electronic address:
Localized high-concentration electrolytes (LHCEs) offer a new methodology to improve the functionality of conventional electrolytes. Understanding the impact of antisolvents on bulk electrolytes is critical to the construction of sophisticated LHCEs. However, the mechanism of how antisolvent modulates the electrochemical reactivity of the solvation structure in LHCEs remains unclear.
View Article and Find Full Text PDFOrganocatalytic Hat Trick: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)-Catalyzed Synthesis of Cyclic Imides via an Amidation-Cyclization-Elimination Cascade.
J Org Chem
January 2025
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.
1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) was used for the synthesis of cyclic imides via an amidation-cyclization-elimination cascade.
View Article and Find Full Text PDFSelective delivery of G-quadruplex ligand in glioma cell lines: the power of cyclic-RGD peptide.
Sci Rep
December 2024
Department of Chemistry, University of Pavia, viale Taramelli, 10, Pavia, 27100, Italy.
Compounds targeting non-canonical secondary structures of nucleic acids, known as G-quadruplexes, are highly cytotoxic, both for cancer and healthy cells, because of their action mechanism's lack of appropriate selectivity. The targeted delivery of cytotoxic molecules to cancer cells is a valuable strategy to expand the repertoire of potential drugs, especially for cancer types for which new therapeutic tools are urgently needed, like glioblastoma. In this work, we conjugated a cyclic arginyl-glycyl-aspartic acid peptide to a naphthalene diimide, previously described as a highly performing stabilizing ligand for DNA G-quadruplexes, to specifically target glioma cells overexpressing RGD-binding integrin receptors.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!