pi-Stacking assisted redox active peptide-gallol conjugate: synthesis of a new generation of low-toxicity antimicrobial silver nanoparticles

Das Manisit; Senapati Kalyan; Panda Sayak Subhra; Bhattacharya Prabuddha; Jana Saibal; Mandal Santi M.; Basak Amit

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pi-Stacking assisted redox active peptide-gallol conjugate: synthesis of a new generation of low-toxicity antimicrobial silver nanoparticles

机译：PI堆叠辅助氧化还原活性肽 - 加仑 - 加仑缀合物：合成新一代低毒性抗微生物纳米粒子

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In this study, we describe the rational design and synthesis of a redox-active petide-gallol conjugate and explore its application in the preparation of antimicrobial silver nanoparticles. Increase in acidity and redox activity of peptide-gallol compounds upon pi-stacking was predicted in silico. A representative phenyl alanine-glycine dipeptide-gallol conjugate was synthesized via click chemistry between N-propargyl dipeptide and azidomethyl pyrogallol. The enhanced redox properties of the conjugate were exemplified by rapid formation of silver nanoparticles (Ag NPs) at room temperature without the need of an external capping agent. The nanoparticles formed were found to exhibit prominent antifungal activity against Candida albicans NCIM 3471 along with robust biofilm eradication ability. Thus, our study established the hypothesis that rationally designed peptide-gallol conjugates can be used as biocompatible, redox-active moieties for in situ generation of non-toxic antimicrobial silver nanoparticles in a fast one pot chemical reduction method.

机译：在这项研究中，我们描述了氧化还原活性物化 - 加仑缀合物的合理设计和合成，并探讨其在抗微生物纳米粒子的制备中的应用。在硅堆叠上预测了肽 - 加仑化合物的酸度和氧化还原活性的增加。通过在N-丙基二肽和氮杂甲基吡替金属之间的咔哒化学合成，合成代表性苯丙氨酸 - 甘氨酸二肽 - 加仑缀合物。通过在室温下快速形成缀合物的增强的氧化还原性能，而不需要外部封端剂。发现形成的纳米颗粒对Candida albicans NCIM 3471具有突出的抗真菌活性以及鲁棒的生物膜消除能力。因此，我们的研究建立了理性设计的肽 - 加仑缀合物可以用作生物相容性，氧化氢活性部分，用于以快速的一种盆栽化学还原方法原位产生无毒抗微生物纳米粒子。

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《RSC Advances》 |2016年第88期|共7页
作者
Das Manisit; Senapati Kalyan; Panda Sayak Subhra; Bhattacharya Prabuddha; Jana Saibal; Mandal Santi M.; Basak Amit;
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Indian Inst Technol Dept Chem Kharagpur 721302 W Bengal India;

Indian Inst Technol Dept Chem Kharagpur 721302 W Bengal India;

Indian Inst Technol Dept Chem Kharagpur 721302 W Bengal India;

Indian Inst Technol Dept Chem Kharagpur 721302 W Bengal India;

Indian Inst Technol Dept Chem Kharagpur 721302 W Bengal India;

Indian Inst Technol Ctr Res Facil Kharagpur 721302 W Bengal India;

Indian Inst Technol Dept Chem Kharagpur 721302 W Bengal India;

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1. pi-Stacking assisted redox active peptide-gallol conjugate: synthesis of a new generation of low-toxicity antimicrobial silver nanoparticles [J] . Das Manisit, Senapati Kalyan, Panda Sayak Subhra, RSC Advances . 2016,第88期

机译：PI堆叠辅助氧化还原活性肽 - 加仑 - 加仑缀合物：合成新一代低毒性抗微生物纳米粒子
2. Single Step Microwave Assisted Synthesis and Antimicrobial Activity of Silver, Copper and Silver-Copper Nanoparticles [J] . Myrna Reyes-Blas, Nadja M. Maldonado-Luna, Carla M. Rivera-Quinones, Advances in Biological Chemistry . 2020,第8期

机译：单步微波辅助合成和抗微生物活性银，铜和银铜纳米粒子
3. Single Step Microwave Assisted Synthesis and Antimicrobial Activity of Silver, Copper and Silver-Copper Nanoparticles [J] . Myrna Reyes-Blas, Nadja M. Maldonado-Luna, Carla M. Rivera-Qui?ones, Journal of Materials Science and Chemical Engineering . 2020,第8期

机译：单步微波辅助合成和抗微生物活性银，铜和银铜纳米粒子
4. Microwave Assisted Green Synthesis and Characterization of Silver Nanoparticles from Hibiscus Leaf Extract and Investigation of their Antimicrobial Activities [C] . Shareefraza J. Ukkund, Darshanram, Zubear Khan, International Conference on Emerging Trends in Mechanical Engineering . 2019

机译：微波辅助绿色合成与芙蓉叶提取物银纳米粒子的表征及其抗菌活性研究
5. Synthesis and Characterization of BSA Conjugated Silver Nanoparticles (Ag/BSA Nanoparticles) and Evaluation of Biological Properties of Ag/BSA Nanoparticles and Ag/BSA Nanoparticles Loaded Poly(hydroxy butyrate valerate) PHBV Films. [D] . Ambaye, Almaz. 2015

机译：BSA共轭银纳米粒子（Ag / BSA纳米粒子）的合成，表征以及负载Ag / BSA纳米粒子和Ag / BSA纳米粒子的聚戊酸羟基丁酸酯PHBV薄膜的生物学性能评估。
6. One pot light assisted green synthesis storage and antimicrobial activity of dextran stabilized silver nanoparticles [O] . Muhammad Ajaz Hussain, Abdullah Shah, Ibrahim Jantan, 2014

机译：一锅光辅助葡聚糖稳定的银纳米颗粒的绿色合成储存和抗菌活性
7. Single Step Microwave Assisted Synthesis and Antimicrobial Activity of Silver, Copper and Silver-Copper Nanoparticles [O] . Myrna Reyes-Blas, Nadja M. Maldonado-Luna, Carla M. Rivera-Quiñones, 2020

机译：单步微波辅助合成和抗微生物活性银，铜和银铜纳米粒子

pi-Stacking assisted redox active peptide-gallol conjugate: synthesis of a new generation of low-toxicity antimicrobial silver nanoparticles

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