Synthesis of new 4-aminobenzoic acid (PABA) hydrazide-hydrazone/sulfonate hybrids and antimicrobial evaluation with ascorbic acid/salicylic acid/N-acetyl cysteine combinations

IF 1.4 4区 化学 Q4 CHEMISTRY, INORGANIC & NUCLEAR
M. İhsan Han , Ufuk İnce , G. Pelin Coşkun , Kaan Birgül , Şengül Dilem Doğan , Amir Ashoorzadeh , Ş. Güniz Küçükgüzel
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Abstract

One of the most serious threats to human health is the increasing prevalence of drug-resistant pathogens. The development of new antibiotics capable of combating drug resistance is critical. In various bacteria and plant species, 4-aminobenzoic acid (PABA) is produced and used as a substrate for folate generation. In this study, a new series of PABA analogs were synthesized and evaluated for their antimicrobial activity. Thirteen novel compounds were prepared by linking PABA hydrazide to sulfonate esters via a hydrazone bridge (4am). The structures of these compounds were characterized by 1H and 13C NMR and FT-IR spectroscopy as well as by LC-MS. Following structural characterization, all compounds were tested for their antimicrobial activity against Staphylococcus aureus (ATCC 29213), Enterococcus faecium (ATCC 19434), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853), and Candida albicans (ATCC 10231) strains. Four compounds were found to have moderate antimicrobial activity against the P. aeruginosa strain. These compounds, including 4e, 4f, 4g, and 4m, containing a hydrazide-hydrazone sulfonate functionality, showed the best MIC value of 64 μg/mL. In addition, synergistic effects of ascorbic acid, salicylic acid, and N-acetyl cysteine (NAC) with synthesized compounds were also investigated. It was observed that the combination of compounds 4f and 4g with NAC showed antipseudomonal activity with MIC values of 32 μg/mL and 16 μg/mL, respectively, against the P. aeuriginosa strain. The antimicrobial activity of 4f and 4g was enhanced by two folds in combination with NAC. Our findings in this study can be crucial for the development of new potent antimicrobial agents.

合成新的 4-氨基苯甲酸(PABA)酰肼-酰肼/磺酸盐混合物,并与抗坏血酸/水杨酸/N-乙酰半胱氨酸组合进行抗菌评估
人类健康面临的最严重威胁之一是抗药性病原体的日益流行。开发能够对抗耐药性的新型抗生素至关重要。在各种细菌和植物物种中,都会产生 4-氨基苯甲酸(PABA),并将其用作生成叶酸的底物。本研究合成了一系列新的 PABA 类似物,并对其抗菌活性进行了评估。通过腙桥将 PABA 酰肼连接到磺酸酯(4a-m),制备出 13 种新型化合物。通过 1H 和 13C NMR、FT-IR 光谱以及 LC-MS 对这些化合物的结构进行了表征。结构表征完成后,测试了所有化合物对金黄色葡萄球菌(ATCC 29213)、粪肠球菌(ATCC 19434)、大肠杆菌(ATCC 25922)、铜绿假单胞菌(ATCC 27853)和白色念珠菌(ATCC 10231)菌株的抗菌活性。发现有四种化合物对铜绿假单胞菌菌株具有中等程度的抗菌活性。包括 4e、4f、4g 和 4m 在内的这些含有酰肼-腙磺酸盐官能团的化合物显示出了 64 μg/mL 的最佳 MIC 值。此外,还研究了抗坏血酸、水杨酸和 N-乙酰半胱氨酸(NAC)与合成化合物的协同作用。结果表明,化合物 4f 和 4g 与 NAC 的组合具有抗假丝酵母菌的活性,对 P. aeuriginosa 菌株的 MIC 值分别为 32 μg/mL 和 16 μg/mL。4f 和 4g 与 NAC 合用后,其抗菌活性提高了两倍。本研究的发现对于开发新的强效抗菌剂至关重要。
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来源期刊
CiteScore
2.60
自引率
7.70%
发文量
103
审稿时长
2.1 months
期刊介绍: Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.
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