Pub Date : 2025-01-01Epub Date: 2025-11-06DOI: 10.1080/10610278.2025.2584997
Jon Chiaramonte, Hunter B D Cheney, Bradley D Smith
Zinc-coordinated bis(dipicolylamine) (ZnBDPA) and its phenoxy derivative (ZnPhenoxyBDPA) are well-known as synthetic receptors with strong affinity for oxyanions, especially phosphorylated biomolecules. Over the last two decades, these synthetic receptors have found broad utility in diverse supramolecular research fields where they enable oxyanion binding, sensing, transport, imaging, or catalysis. TyramineBDPA is a very useful version of the ZnPhenoxyBDPA scaffold, with a reactive primary amine for subsequent conjugation chemistry. Despite its utility and structural simplicity, the preparation and purification of TyramineBDPA can be challenging, especially for inexperienced labs. Presented here is a reproducible, three-step procedure for synthesising and purifying TyramineBDPA on the gram scale, starting from inexpensive and commercially available tyramine. This optimised synthesis will help investigators prepare a wide range of zinc and related dinuclear TyramineBDPA receptors for supramolecular research and development. Proof of utility was gained by conjugating TyramineBDPA to a pyrene fluorophore to create a fluorescent ZnBDPA receptor that revealed new insight regarding receptor clustering under binding conditions where the receptor concentration is high relative to the concentration of phosphate recognition target.
{"title":"Synthesis of tyramine bis(dipicolylamine), a versatile synthetic receptor scaffold for oxyanion recognition.","authors":"Jon Chiaramonte, Hunter B D Cheney, Bradley D Smith","doi":"10.1080/10610278.2025.2584997","DOIUrl":"10.1080/10610278.2025.2584997","url":null,"abstract":"<p><p>Zinc-coordinated bis(dipicolylamine) (<b>ZnBDPA</b>) and its phenoxy derivative (<b>ZnPhenoxyBDPA</b>) are well-known as synthetic receptors with strong affinity for oxyanions, especially phosphorylated biomolecules. Over the last two decades, these synthetic receptors have found broad utility in diverse supramolecular research fields where they enable oxyanion binding, sensing, transport, imaging, or catalysis. <b>TyramineBDPA</b> is a very useful version of the <b>ZnPhenoxyBDPA</b> scaffold, with a reactive primary amine for subsequent conjugation chemistry. Despite its utility and structural simplicity, the preparation and purification of <b>TyramineBDPA</b> can be challenging, especially for inexperienced labs. Presented here is a reproducible, three-step procedure for synthesising and purifying <b>TyramineBDPA</b> on the gram scale, starting from inexpensive and commercially available tyramine. This optimised synthesis will help investigators prepare a wide range of zinc and related dinuclear <b>TyramineBDPA</b> receptors for supramolecular research and development. Proof of utility was gained by conjugating <b>TyramineBDPA</b> to a pyrene fluorophore to create a fluorescent <b>ZnBDPA</b> receptor that revealed new insight regarding receptor clustering under binding conditions where the receptor concentration is high relative to the concentration of phosphate recognition target.</p>","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"36 7-8","pages":"215-223"},"PeriodicalIF":2.6,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12700618/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145757594","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-09-05DOI: 10.1080/10610278.2024.2398575
Ke Luo, Yuanchu Liu, Aimin Li, Zhenzhen Lai, Zhiqing Long, Qing He
Picric acid is known as one of the most dangerous explosive materials and it has become one of the main pollutants in soil and, inter alia, groundwater. To date, many organic or inorganic probes ha...
{"title":"A tetraphenylethylene-based superphane for selective detection and adsorption of trace picric acid in aqueous media","authors":"Ke Luo, Yuanchu Liu, Aimin Li, Zhenzhen Lai, Zhiqing Long, Qing He","doi":"10.1080/10610278.2024.2398575","DOIUrl":"https://doi.org/10.1080/10610278.2024.2398575","url":null,"abstract":"Picric acid is known as one of the most dangerous explosive materials and it has become one of the main pollutants in soil and, inter alia, groundwater. To date, many organic or inorganic probes ha...","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"7 1","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142221599","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-08-22DOI: 10.1080/10610278.2024.2394465
Sreejith Sudhakaran Jayabhavan, Hemanadhan Myneni, Morris Riedel, Krishna K. Damodaran
The role of the structural similarity in the individual components on the self-assembly process of multi-component systems was studied by analysing the gelation properties of chiral multi-component...
通过分析手性多组分系统的凝胶特性，研究了各组分结构相似性对多组分系统自组装过程的影响。
{"title":"Analysing the self-assembly modes in chiral multi-component gels based on donor and acceptor moieties","authors":"Sreejith Sudhakaran Jayabhavan, Hemanadhan Myneni, Morris Riedel, Krishna K. Damodaran","doi":"10.1080/10610278.2024.2394465","DOIUrl":"https://doi.org/10.1080/10610278.2024.2394465","url":null,"abstract":"The role of the structural similarity in the individual components on the self-assembly process of multi-component systems was studied by analysing the gelation properties of chiral multi-component...","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"6 1","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142221595","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-08-11DOI: 10.1080/10610278.2024.2387256
Gulshan Kumar Mishra, Aayushi Raut, Mahesh Vasava, C. Aryajyothis, Riya Khandelwal
The use of excessive pesticides, including fungicides, insecticides, and herbicides, in agriculture has increased particularly as they can pollute the environment and perhaps have negative health i...
{"title":"Advancements in luminescent supramolecular compounds for the detection of pesticides residue: a comprehensive review","authors":"Gulshan Kumar Mishra, Aayushi Raut, Mahesh Vasava, C. Aryajyothis, Riya Khandelwal","doi":"10.1080/10610278.2024.2387256","DOIUrl":"https://doi.org/10.1080/10610278.2024.2387256","url":null,"abstract":"The use of excessive pesticides, including fungicides, insecticides, and herbicides, in agriculture has increased particularly as they can pollute the environment and perhaps have negative health i...","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"5 1","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-08-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142221596","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-08-07DOI: 10.1080/10610278.2024.2388731
Hailey S. Sanders, Kirk M. Atkinson, Bradley D. Smith
Prior studies have shown that fluorescent molecular probes based on cyclopropyl esters are good substrates for butyrylcholine esterase (BChE), which is a biomarker of several human diseases. We tes...
{"title":"Fluorescent cyclopropyl ester probes are efficiently cleaved by endogenous carboxylesterase in mouse blood: implications for preclinical fluorescence imaging","authors":"Hailey S. Sanders, Kirk M. Atkinson, Bradley D. Smith","doi":"10.1080/10610278.2024.2388731","DOIUrl":"https://doi.org/10.1080/10610278.2024.2388731","url":null,"abstract":"Prior studies have shown that fluorescent molecular probes based on cyclopropyl esters are good substrates for butyrylcholine esterase (BChE), which is a biomarker of several human diseases. We tes...","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"199 1","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-08-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141945051","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-08-04DOI: 10.1080/10610278.2024.2381542
James E. M. Lewis, Timothy L. Easun, Timothy A. Barendt, Ben E. Barber, Jake L. Greenfield, Anna J. McConnell, Georgia R. F. Orton, Sophie C. Patrick, Connor Prior, Jiarong Wu
Supramolecular chemistry encompasses critical aspects found throughout the chemical sciences. Despite its ubiquity, the concept of supramolecular chemistry as a defined field of research is relativ...
{"title":"MASC 2023: remembering the past, celebrating the present and looking to the future","authors":"James E. M. Lewis, Timothy L. Easun, Timothy A. Barendt, Ben E. Barber, Jake L. Greenfield, Anna J. McConnell, Georgia R. F. Orton, Sophie C. Patrick, Connor Prior, Jiarong Wu","doi":"10.1080/10610278.2024.2381542","DOIUrl":"https://doi.org/10.1080/10610278.2024.2381542","url":null,"abstract":"Supramolecular chemistry encompasses critical aspects found throughout the chemical sciences. Despite its ubiquity, the concept of supramolecular chemistry as a defined field of research is relativ...","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"26 1","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-08-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141945050","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-08-02DOI: 10.1080/10610278.2024.2384908
William Murrell, Carol Hua, Fred Pfeffer
In recent studies, n→π* interactions featuring nucleophilic pyridine have been investigated using Fourier transform microwave spectroscopy and high-level theoretical computations. Examples of n→π* ...
{"title":"Conformational stabilisation of a 2-pyridyl imide by n→π* interaction in solid state","authors":"William Murrell, Carol Hua, Fred Pfeffer","doi":"10.1080/10610278.2024.2384908","DOIUrl":"https://doi.org/10.1080/10610278.2024.2384908","url":null,"abstract":"In recent studies, n→π* interactions featuring nucleophilic pyridine have been investigated using Fourier transform microwave spectroscopy and high-level theoretical computations. Examples of n→π* ...","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"25 1","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141886094","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-07-30DOI: 10.1080/10610278.2024.2386413
Kay T. Xia
Supramolecular chemistry is, broadly, the study of noncovalent interactions. Electrochemistry inherently involves supramolecular organisation of ions and solvent, so the use of supramolecular chemi...
{"title":"Towards applications of supramolecular host–guest electrochemistry","authors":"Kay T. Xia","doi":"10.1080/10610278.2024.2386413","DOIUrl":"https://doi.org/10.1080/10610278.2024.2386413","url":null,"abstract":"Supramolecular chemistry is, broadly, the study of noncovalent interactions. Electrochemistry inherently involves supramolecular organisation of ions and solvent, so the use of supramolecular chemi...","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"124 1","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141863027","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-07-03DOI: 10.1080/10610278.2024.2374722
Cally J. E. Haynes, Nicholas G. White
Published in Supramolecular Chemistry (Ahead of Print, 2024)
发表于《超分子化学》（2024 年预刊）
{"title":"(Self) assembled news: recent highlights from the supramolecular chemistry literature (quarter 2, 2024)","authors":"Cally J. E. Haynes, Nicholas G. White","doi":"10.1080/10610278.2024.2374722","DOIUrl":"https://doi.org/10.1080/10610278.2024.2374722","url":null,"abstract":"Published in Supramolecular Chemistry (Ahead of Print, 2024)","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"35 1","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141719372","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-04-04DOI: 10.1080/10610278.2024.2338141
Míriam Pujals, Valentina Iannace, Xavi Ribas
Regioselective poly-functionalization of fullerenes is highly desired to boost the applicability of pure-isomer poly-adducts. Here, we show how the supramolecular nanocapsule 1·(BArF)8 acts as a su...
{"title":"Two-fold enhancement of equatorial bis-PCBM-C60 adducts using a supramolecular mask","authors":"Míriam Pujals, Valentina Iannace, Xavi Ribas","doi":"10.1080/10610278.2024.2338141","DOIUrl":"https://doi.org/10.1080/10610278.2024.2338141","url":null,"abstract":"Regioselective poly-functionalization of fullerenes is highly desired to boost the applicability of pure-isomer poly-adducts. Here, we show how the supramolecular nanocapsule 1·(BArF)8 acts as a su...","PeriodicalId":22084,"journal":{"name":"Supramolecular Chemistry","volume":"6 1","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140594059","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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