{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T02:27:07Z","timestamp":1740104827850,"version":"3.37.3"},"reference-count":50,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2017,10,30]],"date-time":"2017-10-30T00:00:00Z","timestamp":1509321600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"Cineca, Bologna, Italy"},{"name":"Regione Lombardia for the LISA","award":["LI08p_ChiPhyto"],"award-info":[{"award-number":["LI08p_ChiPhyto"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2018,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Vibrational and electronic circular dichroism (VCD and ECD) spectra of 3 optically active bilirubin analogs with propionic acid groups replaced by (1) 1\u2010(S)\u2010methylpropyl groups, (2) 3\u2010acetoxy\u20101\u2010(S)\u2010methylpropyl groups, and (3) 1\u2010(S)\u20102\u2010(R)\u2010dimethyl\u20102\u2010(methoxycarbonyl)ethyl groups have been recorded at different concentrations in chloroform. The aliphatic chains attached to C\u20108 and C\u201012 of the 3 chosen mesobilirubins were modified so as to possess no OH group. The variation of the VCD spectra with concentration is consistent with the formation of dimers at high concentration. Density functional theory and time\u2010dependent density functional theory calculations on monomeric and dimeric forms support such a conclusion. Comparing with previous VCD (ECD) and IR (UV) studies of other mesobilirubin molecules, it is concluded that here, the key feature for aggregation is the missing OH groups on the propionic acid chains. The latter, in synergy with the polar groups of lactam moieties, appear to be involved in intramolecular phenomena and thus favor monomeric forms. Investigation of ECD and UV spectra of the same compounds in mixed DMSO\/chloroform solutions provide further clues to the proposed picture.<\/jats:p>","DOI":"10.1002\/chir.22776","type":"journal-article","created":{"date-parts":[[2017,10,30]],"date-time":"2017-10-30T12:16:37Z","timestamp":1509365797000},"page":"19-28","source":"Crossref","is-referenced-by-count":8,"title":["On the aggregation of bilirubinoids in solution as evidenced by <scp>VCD<\/scp> and <scp>ECD<\/scp> spectroscopy and <scp>DFT<\/scp> calculations"],"prefix":"10.1002","volume":"30","author":[{"given":"Simone","family":"Ghidinelli","sequence":"first","affiliation":[{"name":"Dipartimento di Medicina Molecolare e Traslazionale Universit\u00e0 di Brescia  Brescia Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Giovanna","family":"Longhi","sequence":"additional","affiliation":[{"name":"Dipartimento di Medicina Molecolare e Traslazionale Universit\u00e0 di Brescia  Brescia Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Giuseppe","family":"Mazzeo","sequence":"additional","affiliation":[{"name":"Dipartimento di Medicina Molecolare e Traslazionale Universit\u00e0 di Brescia  Brescia Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9359-1214","authenticated-orcid":false,"given":"Sergio","family":"Abbate","sequence":"additional","affiliation":[{"name":"Dipartimento di Medicina Molecolare e Traslazionale Universit\u00e0 di Brescia  Brescia Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Stefan E.","family":"Boiadjiev","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Medical University\u2010Pleven  Pleven Bulgaria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"David A.","family":"Lightner","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Nevada  Reno Nevada USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2017,10,30]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-7091-6938-4"},{"key":"e_1_2_6_3_1","doi-asserted-by":"crossref","first-page":"798","DOI":"10.1007\/978-3-7091-1637-1","volume-title":"Bilirubin: Jekyll and Hyde Pigment of Life (Progress in the Chemistry of Organic Natural Products)","author":"Lightner DA","year":"2013"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.18641320311"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1515\/bchm2.1942.274.1-6.231"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/262326a0"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1098\/rspb.1978.0066"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)90304-7"},{"key":"e_1_2_6_9_1","doi-asserted-by":"crossref","first-page":"2456","DOI":"10.1021\/ja00294a042","article-title":"Bilirubin enantiomer selection by cyclodextrins","volume":"10","author":"Lightner DA","year":"1985","journal-title":"J Am Chem Soc"},{"key":"e_1_2_6_10_1","doi-asserted-by":"crossref","first-page":"16669","DOI":"10.1016\/S0021-9258(18)37442-8","article-title":"Understanding bilirubin conformation and binding. Circular dichroism of human serum albumin with bilirubin and its esters","volume":"263","author":"Lightner DA","year":"1988","journal-title":"J Biol Chem"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00009a055"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00052a006"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00080a006"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp3013255"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00255a020"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1080\/00387018308062390"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(97)01066-1"},{"key":"e_1_2_6_18_1","doi-asserted-by":"crossref","first-page":"1047","DOI":"10.1007\/s007060070036","article-title":"On the molecularity of bilirubins and their esters and anions in chloroform solution","volume":"131","author":"Brower JO","year":"2000","journal-title":"Monatsh Chem"},{"key":"e_1_2_6_19_1","doi-asserted-by":"crossref","first-page":"741","DOI":"10.1007\/PL00013483","article-title":"Solution structure of mesobilirubin\u2010XIII\u03b1 bridged between the propionic acid substituents","volume":"129","author":"Crusats J","year":"1998","journal-title":"Monatsh Chem"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)86316-X"},{"key":"e_1_2_6_21_1","doi-asserted-by":"crossref","first-page":"203","DOI":"10.1007\/s007060170131","article-title":"Hydrogen\u2010bonded dimers in dipyrrinones and acyl dipyrrinones","volume":"132","author":"Huggins MT","year":"2001","journal-title":"Monatsh Chem"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo972227r"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00087-9"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo000393k"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00109-0"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00139a005"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/0957-4166(95)00301-5"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1080\/00304940609355999"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi0481491"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570370431"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF00911086"},{"key":"e_1_2_6_30_3","doi-asserted-by":"crossref","first-page":"323","DOI":"10.1007\/978-3-7091-6938-4","volume-title":"The Chemistry of Linear Oligopyrroles and Bile Pigments","author":"Falk H","year":"1989"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/9781119976516"},{"volume-title":"Chiroptical Spectroscopy: Fundamentals and Applications","year":"2017","author":"Polavarapu PL","key":"e_1_2_6_32_1"},{"key":"e_1_2_6_33_1","first-page":"621","volume-title":"Circular Dichroism Principles and Applications","author":"Keiderling TA","year":"2000"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1201\/b12278"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp037698y"},{"issue":"1","key":"e_1_2_6_36_1","doi-asserted-by":"crossref","DOI":"10.1063\/1.2806192","article-title":"Lactic acid in solution: investigations of lactic acid self\u2010aggregation and hydrogen bonding interactions with water and methanol using vibrational absorption and vibrational circular dichroism spectroscopies","volume":"128","author":"Losada M","year":"2008","journal-title":"J Chem Phys"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja9910513"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja050483c"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja074188z"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2007.08.023"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ab.2009.05.040"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ab.2012.03.023"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/0957-4166(96)00148-6"},{"volume-title":"Gaussian","year":"2009","author":"Gaussian 09, Revision A.02","key":"e_1_2_6_44_1"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr9904009"},{"key":"e_1_2_6_46_1","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1016\/j.theochem.2009.06.039","article-title":"A full conformational space analysis of bilirubin","volume":"911","author":"Hissi EGV","year":"2009","journal-title":"J Mol Struct (THEOCHEM)"},{"key":"e_1_2_6_47_1","unstructured":"PC model version 9. Serena software Inc. Bloomington IN USA. Force field MMX a variant of Allinger's MM2 force field."},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100251a006"},{"key":"e_1_2_6_49_1","unstructured":"GhidinelliS.Chiroptical studies of conformation of bilirubin in different solvents and in interaction with serum albumin in presence of anaesthetics. Universit\u00e0 di Brescia BSc Degree Thesis 2016. (this reference may be provided on request to the interested reader by the authors)"}],"container-title":["Chirality"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchir.22776","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.22776","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,29]],"date-time":"2023-09-29T08:40:14Z","timestamp":1695976814000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chir.22776"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,10,30]]},"references-count":50,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2018,1]]}},"alternative-id":["10.1002\/chir.22776"],"URL":"https:\/\/doi.org\/10.1002\/chir.22776","archive":["Portico"],"relation":{},"ISSN":["0899-0042","1520-636X"],"issn-type":[{"type":"print","value":"0899-0042"},{"type":"electronic","value":"1520-636X"}],"subject":[],"published":{"date-parts":[[2017,10,30]]}}}