Novel Cationic Bolaamphiphiles for Protein and DNA Binding, Gene Delivery, and Antimicrobial Applications.

IF 3.5 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Chemistry - An Asian Journal Pub Date : 2025-01-16 DOI:10.1002/asia.202401582

Pabitra Mondal, Sadhana Roy, Dipanwita Patra, Somdeb Bose Dasgupta, Joykrishna Dey

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Abstract

In this study, we have designed and developed a cationic bolaform C₁₂-(2,3-dihydroxy-N, N-dimethyl-N-(2-ureidoethyl)propan-1-aminium chloride)₂ (C₁₂(DDUPAC)₂) that is derived from biocompatible molecules. The bolaform C₁₂(DDUPAC)₂ has hydroxyl (OH) functionality at both the cationic head groups. The impact of head group structure on the self-assembly and effectiveness of gene transfection and antimicrobial activity was investigated and compared with that of the hydrochloride salt C₁₂-(N, N-dimethyl-N-(2-ureidoethan-1-aminium chloride)₂ (C₁₂(DUAC)₂) of its precursor molecule. The formation of spherical as well as rod-like self-assembled structures was found to occur above a relatively low critical aggregation concentration (CAC) by the bolaforms. The results of calorimetric measurements demonstrated thermodynamically favorable aggregation in water. Interaction studies of the cationic bolaforms with the calf thymus DNA revealed stronger binding of C₁₂(DDUPAC)₂ in comparison to C₁₂(DUAC)₂, which explained higher in vitro gene transfection efficiency of C₁₂(DDUPAC)₂ than C₁₂(DUAC)₂. Both bolaforms interact weakly with the bovine serum albumin protein. MTT-based in vitro cytotoxicity assay was performed and both bolaforms were found to have marginal cytotoxicity. Further, both bolaforms exhibit advantageous antibacterial activity against E. coli and potent antifungal activity against Fusarium oxysporum at high dosages.

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用于蛋白质和DNA结合、基因传递和抗菌应用的新型阳离子亲水分子。

在这项研究中，我们设计并开发了一种来自生物相容性分子的阳离子bolaform C12-（2,3-二羟基- n， n-二甲基- n-（2-脲基乙基）丙烷-1-氯化铵）2 （C12(DDUPAC)2）。bolaform C12(DDUPAC)2在两个阳离子头基上都具有羟基（OH）官能团。研究了头基结构对其自组装、基因转染效果及抑菌活性的影响，并与其前体分子C12-(N， N-二甲基-N-（2-脲基比1-氯化铵）2 （C12(DUAC)2）的抑菌活性进行了比较。发现在相对较低的临界聚集浓度（CAC）以上，形成球形和棒状自组装结构。量热测量的结果表明，在热力学上有利于水中的聚集。研究结果表明，与C12(DUAC)2相比，C12(DDUPAC)2与小牛胸腺DNA的结合更强，这说明C12(DDUPAC)2的体外基因转染效率高于C12(DUAC)2。两种bolaforms与牛血清白蛋白的相互作用都很弱。以mtt为基础的体外细胞毒性试验发现，两种bolaforms均具有边际细胞毒性。此外，这两种bolaforms在高剂量下对大肠杆菌和尖孢镰刀菌均表现出有利的抗菌活性。

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来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).