Synthesis and biological evaluation of new nanosized aromatic polyamides containing amido- and sulfonamidopyrimidines pendant structures

Chemistry Central Journal

Hammed H A M Hassan²  Elsayed M E Mansour²  Asmaa M S Abou Zeid²  Ehab R El-Helow¹  Amel F Elhusseiny²  Raafat Soliman³ 

[1] Department of Microbiology and Immunology, Faculty of Pharmacy, Pharos University, Canal El Mahmoudia Street, Alexandria 21311, Egypt

[2] Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, Alexandria 21321, Egypt

[3] Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Alexandria University, Alexandria, Egypt

关键词: Microbial activity;    Pyrimidines;    Sulfonamides;    Polymers;    Synthesis;   

Others  :  1223569
DOI  :  10.1186/s13065-015-0123-2

 received in 2015-04-12, accepted in 2015-08-05,  发布年份 2015

【 摘 要 】

Background

Antibiotics are biocides or products that inhibit the growth of microorganisms in the living cells and there are extensive works directed to develop efficient antimicrobial agents. The sulfonamide-containing polymers have great potential to resist gram-positive or gram-negative bacterial and fungal attacks. As a therapeutic agent, the sulfonamides have been reported as antitumor and antimicrobial agents against bacteria, being more potent against gram positive rather than gram negative strains. Design of new classes of inhibitors bearing fluorescent tails, as therapeutic and imaging agents, is currently an active area of research. Here, we describe the synthesis of a new family of polyamides based on chlorophenyl-3,5-diaminobenzamides, methyl substituted pyrimidinoamido-3,5-diamino- benzamides and methyl substituted pyrimidinosulfonamido-3,5-diaminobenzamides and evaluation of their thermal, optical and antimicrobial properties.

Results

We report the synthesis of a new series of nanosized polyamides containing bioactive pendent structures. The spherical nanosized polymer particles are soluble in many organic solvents and exhibited emissions ranging from blue to orange wavelength depending on the nature of the signaling unit. Pyrimidine- and p-chloroaromatic containing polymers exhibited higher bioactivity than that contain the sulfonamide group. The amidopyrimidine polymers exhibited remarkable antifungal and antibacterial activity and thus, these types of polymers are promising candidates for biomedical applications.

Conclusions

The SEM analysis indicated that most of the polyamides were organized as well defined nano sized spheres, but in certain derivatives small amount of aggregated nanospheres were also observed. Thermal analyses were studied up to 700 °C and results showed comparable thermal behavior. The optical results revealed that polymeric series (A) exhibited orange emission, series (B) showed green emission while series (C) exhibited yellow and blue emissions. Benzene/pyridine structure interchange resulted in red shifted peaks attributed to the localized lone pair of electrons on a nitrogen atom which offer a greater electron affinity and better electron-transporting properties. The amido- and sulfonamide pyrimidine containing polymers exhibited the most potent antimicrobial activity. Relative to the reference Gentamicin, the polymer 54 exhibited comparable antibacterial activity against gram negative bacteria. Analogues 52 and 57 exhibited remarkable antibacterial activities compared to the references used. Thus, these polyamides are likely to be promising broad spectrum antibacterial agents and deserve further investigation at the molecular level.

【 授权许可】

   
2015 Hassan et al.

【 图 表 】

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