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First, we describe the synthesis of methylene bridged glycoluril dimers capped with aromatic sidewalls which allowed us to probe the interconversion of the S\u2010 and C\u2010shaped dimers which is a fundamental step in CB[n] formation. The C\u2010shaped compounds were found to undergo discrete self\u2010assembly (dimerization) in both water and organic solvents which lead us to investigate multicomponent self\u2010sorting systems. We supressed the self\u2010association of <jats:bold>8<\/jats:bold> by electrostatic repulsion in the putative dimer which allowed expression of its innate molecular recognition properties toward methylene blue and related planar cationic dyes. Longer glycoluril oligomers (trimer\u2010hexamer, acyclic decamer) were prepared by starving the CB[n]\u2010forming reaction of formaldehyde. The longer oligomers (e.\u2009g. <jats:bold>15<\/jats:bold> and <jats:bold>16<\/jats:bold>) bind to alkylammonium ions in water \u2248100\u2010fold weaker than macrocyclic CB[n] highlighting the high preorganization of the acyclic but polycyclic framework. We prepared a wide variety of acyclic CB[n] compounds (wall variants, solubilizing group variants, linker variants) based on glycoluril trimer and tetramer. In particular, <jats:bold>26<\/jats:bold> and <jats:bold>27<\/jats:bold> have been shown to possess a wide variety of chemically and biologically interesting functions. For example, <jats:bold>26<\/jats:bold> was used to formulate the insoluble drug Albendazole and treat mice bearing SK\u2010OV\u20103 xenograft tumors. Compound <jats:bold>27<\/jats:bold> binds tightly to the neuromuscular blocking agents rocuronium, vecuronium, and cisatracurium and acts as an <jats:italic>in\u2005vivo<\/jats:italic> reversal agent for these compounds in anesthetized rats. Container <jats:bold>27<\/jats:bold> was also found to modulate the hyperlocomotive effect of rats that had been treated with methamphetamine. Finally, <jats:bold>38<\/jats:bold> has been used as a cross reactive component of sensor arrays that are capable of classifying and quantifying cancer related nitroamine and a range of over the counter drugs. Overall, the work demonstrates that acyclic CB[n]\u2010type compounds are nicely pre\u2010organized and therefore retain the essential aspects of the recognition properties of macrocyclic CB[n] but allow for more straightforward tailoring of structure and solubility that enables a variety of chemically and biologically important applications.<\/jats:p>","DOI":"10.1002\/ijch.201700098","type":"journal-article","created":{"date-parts":[[2017,11,14]],"date-time":"2017-11-14T10:23:35Z","timestamp":1510655015000},"page":"250-263","source":"Crossref","is-referenced-by-count":77,"title":["Acyclic Cucurbit[n]uril\u2010type Receptors: Preparation, Molecular Recognition Properties and Biological Applications"],"prefix":"10.1002","volume":"58","author":[{"given":"Shweta","family":"Ganapati","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry University of Maryland College Park  College Park Maryland 20742 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lyle","family":"Isaacs","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry University of Maryland College Park  College Park Maryland 20742 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2017,11,14]]},"reference":[{"key":"e_1_2_5_2_1","unstructured":"\u00a0"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00414a070"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja993376p"},{"key":"e_1_2_5_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo015897c"},{"key":"e_1_2_5_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020118)41:2<275::AID-ANIE275>3.0.CO;2-M"},{"key":"e_1_2_5_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja056287n"},{"key":"e_1_2_5_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201210267"},{"key":"e_1_2_5_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b01842"},{"key":"e_1_2_5_10_1","unstructured":"\u00a0"},{"key":"e_1_2_5_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja303309e"},{"key":"e_1_2_5_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/C1RA00768H"},{"key":"e_1_2_5_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar500075g"},{"key":"e_1_2_5_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00273C"},{"key":"e_1_2_5_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00341"},{"key":"e_1_2_5_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00631G"},{"key":"e_1_2_5_17_1","volume-title":"Container Molecules and Their Guests","author":"Cram D. 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