{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,5]],"date-time":"2026-04-05T07:30:06Z","timestamp":1775374206983,"version":"3.50.1"},"reference-count":48,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2022,11,30]],"date-time":"2022-11-30T00:00:00Z","timestamp":1669766400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002261","name":"Russian Foundation for Basic Research","doi-asserted-by":"publisher","award":["20-03-00816"],"award-info":[{"award-number":["20-03-00816"]}],"id":[{"id":"10.13039\/501100002261","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Nanomaterials"],"abstract":"<jats:p>Novel monosubstituted pillar[5]arenes with one or two terminal carboxyl groups were synthesized by the reaction of succinic anhydride with pillar[5]arene derivative containing a diethylenetriamine function. The ability for non-covalent self-assembly in chloroform, dimethyl sulfoxide, as well as in tetrahydrofuran-water system was studied. The ability of the synthesized macrocycles to form different types of associates depending on the substituent nature was established. The formation of stable particles with average diameter of 192 nm in chloroform and of 439 nm in DMSO was shown for pillar[5]arene containing two carboxyl fragments. Solid lipid nanoparticles (SLN) based on monosubstituted pillar[5]arenes were synthesized by nanoprecipitation in THF-water system. Minor changes in the structure of the macrocycle substituent can dramatically influence the stability and shape of SLN (spherical and rod-like structures) accordingly to DLS and TEM. The presence of two carboxyl groups in the macrocycle substituent leads to the formation of stable spherical SLN with an average hydrodynamic diameter of 364\u2013454 nm. Rod-like structures are formed by pillar[5]arene containing one carboxyl fragment, which diameter is about of 50\u201380 nm and length of 700\u20131000 nm. The synthesized stable SLN open up great prospects for their use as drug storage systems.<\/jats:p>","DOI":"10.3390\/nano12234266","type":"journal-article","created":{"date-parts":[[2022,11,30]],"date-time":"2022-11-30T09:18:36Z","timestamp":1669799916000},"page":"4266","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Solid Lipid Nanoparticles Based on Monosubstituted Pillar[5]arenes: Chemoselective Synthesis of Macrocycles and Their Supramolecular Self-Assembly"],"prefix":"10.3390","volume":"12","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7837-8976","authenticated-orcid":false,"given":"Darya","family":"Filimonova","sequence":"first","affiliation":[{"name":"A.M. Butlerov Chemistry Institute, Kazan Federal University, 18 Kremlyovskaya Str., 420008 Kazan, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4540-2364","authenticated-orcid":false,"given":"Anastasia","family":"Nazarova","sequence":"additional","affiliation":[{"name":"A.M. Butlerov Chemistry Institute, Kazan Federal University, 18 Kremlyovskaya Str., 420008 Kazan, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3956-6637","authenticated-orcid":false,"given":"Luidmila","family":"Yakimova","sequence":"additional","affiliation":[{"name":"A.M. Butlerov Chemistry Institute, Kazan Federal University, 18 Kremlyovskaya Str., 420008 Kazan, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3019-7866","authenticated-orcid":false,"given":"Ivan","family":"Stoikov","sequence":"additional","affiliation":[{"name":"A.M. Butlerov Chemistry Institute, Kazan Federal University, 18 Kremlyovskaya Str., 420008 Kazan, Russia"},{"name":"Federal State Budgetary Scientific Institution \u00abFederal Center for Toxicological, Radiation, and Biological Safety\u00bb, Nauchny Gorodok-2, 420075 Kazan, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,11,30]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2283","DOI":"10.1016\/S0142-9612(01)00362-3","article-title":"Production of lipospheres as carriers for bioactive compounds","volume":"23","author":"Cortesi","year":"2002","journal-title":"Biomaterials"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"184","DOI":"10.1016\/j.nano.2008.08.003","article-title":"Effect of lipid core material on characteristics of solid lipid nanoparticles designed for oral lymphatic delivery","volume":"5","author":"Paliwal","year":"2009","journal-title":"Nanomed. Nanotechnol. Biol. 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