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In the current study, we evaluated the effects of \u03b1-cyclodextrin, \u03b2-cyclodextrin, or methyl-\u03b2-cyclodextrin supplementation to a synthetic culture medium on biomass and spiramycin production by Streptomyces ambofaciens ATCC 23877. We found a high stimulatory effect on spiramycin production when the culture medium was supplemented with 0.5% (w\/v) methyl-\u03b2-cyclodextrin, whereas \u03b1-cyclodextrin or \u03b2-cyclodextrin weakly enhanced antibiotic yields. As the stimulation of antibiotic production could be because of spiramycin complexation with cyclodextrins with effects on antibiotic stability and\/or efflux, we analyzed the possible formation of complexes by physical\u2013chemical methods. The results of Job plot experiment highlighted the formation of a nonhost@guest complex methyl-\u03b2-cyclodextrin@spiramycin I in the stoichiometric ratio of 3:1 while they excluded the formation of complex between spiramycin I and \u03b1- or \u03b2-cyclodextrin. Fourier-transform infrared spectroscopy measurements were then carried out to characterize the methyl-\u03b2-cyclodextrin@spiramycin I complex and individuate the chemical groups involved in the binding mechanism. These findings may help to improve the spiramycin fermentation process, providing at the same time a new device for better delivery of the antibiotic at the site of infection by methyl-\u03b2-cyclodextrin complexation, as it has been well-documented for other bioactive molecules.<\/jats:p>","DOI":"10.1021\/acsomega.7b01766","type":"journal-article","created":{"date-parts":[[2018,3,1]],"date-time":"2018-03-01T06:34:39Z","timestamp":1519886079000},"page":"2470-2478","source":"Crossref","is-referenced-by-count":12,"title":["Stimulatory Effects of Methyl-\u03b2-cyclodextrin\non Spiramycin Production and Physical\u2013Chemical Characterization\nof Nonhost@Guest Complexes"],"prefix":"10.1021","volume":"3","author":[{"given":"Matteo","family":"Calcagnile","sequence":"first","affiliation":[{"name":"University of Salento , , Via Monteroni , ,","place":["Lecce, Italy, 73100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5506-5413","authenticated-orcid":true,"given":"Simona","family":"Bettini","sequence":"additional","affiliation":[{"name":"University of Salento , , Via Monteroni , ,","place":["Lecce, Italy, 73100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fabrizio","family":"Damiano","sequence":"additional","affiliation":[{"name":"University of Salento , , Via Monteroni , ,","place":["Lecce, Italy, 73100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3275-8660","authenticated-orcid":true,"given":"Adelfia","family":"Tala\u0300","sequence":"additional","affiliation":[{"name":"University of Salento , , Via Monteroni , ,","place":["Lecce, Italy, 73100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Salvatore M.","family":"Tredici","sequence":"additional","affiliation":[{"name":"University of Salento , , Via Monteroni , ,","place":["Lecce, Italy, 73100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rosanna","family":"Pagano","sequence":"additional","affiliation":[{"name":"University of Salento , , Via Monteroni , ,","place":["Lecce, Italy, 73100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marco","family":"Di Salvo","sequence":"additional","affiliation":[{"name":"University of Salento , , Via Monteroni , ,","place":["Lecce, Italy, 73100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luisa","family":"Siculella","sequence":"additional","affiliation":[{"name":"University of Salento , , Via Monteroni , ,","place":["Lecce, Italy, 73100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniela","family":"Fico","sequence":"additional","affiliation":[{"name":"University of Salento , , Via Monteroni , ,","place":["Lecce, Italy, 73100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Giuseppe E.","family":"De Benedetto","sequence":"additional","affiliation":[{"name":"University of Salento , , Via Monteroni , ,","place":["Lecce, Italy, 73100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ludovico","family":"Valli","sequence":"additional","affiliation":[{"name":"University of Salento , , Via Monteroni , ,","place":["Lecce, Italy, 73100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3768-7275","authenticated-orcid":true,"given":"Pietro","family":"Alifano","sequence":"additional","affiliation":[{"name":"University of Salento , , Via Monteroni , ,","place":["Lecce, Italy, 73100"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2018,3,1]]},"reference":[{"key":"2026090206302541600_cit1","doi-asserted-by":"publisher","first-page":"1762","DOI":"10.1128\/aac.05183-11","article-title":"Significant reduction\nof brain cysts caused by Toxoplasma gondii after treatment with spiramycin\ncoadministered with metronidazole in a mouse model of chronic toxoplasmosis","volume":"56","author":"Chew","year":"2012","journal-title":"Antimicrob. Agents Chemother."},{"key":"2026090206302541600_cit2","doi-asserted-by":"publisher","first-page":"347","DOI":"10.1093\/jac\/dki013","article-title":"Concentrations and\nin vivo antibacterial activity of spiramycin and metronidazole in\npatients with periodontitis treated with high-dose metronidazole and\nthe spiramycin\/metronidazole combination","volume":"55","author":"Poulet","year":"2005","journal-title":"J.\nAntimicrob. Chemother."},{"key":"2026090206302541600_cit3","first-page":"702","article-title":"New species\nof Streptomyces producing antibiotics Streptomyces ambofaciens n.\nsp., cultural characteristics","volume":"87","author":"Pinnert-Sindico","year":"1954","journal-title":"Ann. Inst. Pasteur"},{"key":"2026090206302541600_cit4","doi-asserted-by":"publisher","first-page":"117","DOI":"10.1016\/j.jbiotec.2015.09.020","article-title":"Complete genome\nsequence of Streptomyces\nambofaciens ATCC 23877, the spiramycin producer","volume":"214","author":"Thibessard","year":"2015","journal-title":"J. Biotechnol."},{"key":"2026090206302541600_cit5","first-page":"1498","article-title":"Trypanocide\naction of an antibiotic produced by a Streptomyces","volume":"234","author":"Cosar","year":"1952","journal-title":"C. R. Hebd. Seances Acad. Sci."},{"key":"2026090206302541600_cit6","doi-asserted-by":"publisher","first-page":"251","DOI":"10.1007\/s10295-013-1379-y","article-title":"Genome mining of\nStreptomyces ambofaciens","volume":"41","author":"Aigle","year":"2014","journal-title":"J. Ind. Microbiol.\nBiotechnol."},{"key":"2026090206302541600_cit7","doi-asserted-by":"publisher","first-page":"231","DOI":"10.1016\/s0378-1119(96)00565-3","article-title":"Production\nof a novel polyketide through the construction of a hybrid polyketide\nsynthase","volume":"183","author":"Kuhstoss","year":"1996","journal-title":"Gene"},{"key":"2026090206302541600_cit8","doi-asserted-by":"publisher","first-page":"4111","DOI":"10.1099\/mic.0.2007\/009746-0","article-title":"Organization of the biosynthetic\ngene cluster for the macrolide antibiotic spiramycin in Streptomyces\nambofaciens","volume":"153","author":"Karray","year":"2007","journal-title":"Microbiology"},{"key":"2026090206302541600_cit9","doi-asserted-by":"publisher","first-page":"593","DOI":"10.7164\/antibiotics.32.593","article-title":"Bioconversion\nand biosynthesis\nof 16-membered macrolide antibiotics. XIII. 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Eng."},{"key":"2026090206302541600_cit17","doi-asserted-by":"publisher","first-page":"1003","DOI":"10.1099\/00221287-139-5-1003","article-title":"Resistance\nto spiramycin in Streptomyces ambofaciens, the producer organism,\ninvolves at least two different mechanisms","volume":"139","author":"Pernodet","year":"1993","journal-title":"J. Gen. Microbiol."},{"key":"2026090206302541600_cit18","doi-asserted-by":"publisher","first-page":"689","DOI":"10.1631\/jzus.2004.0689","article-title":"Improved production\nof spiramycin by mutant Streptomyces\nambofaciens","volume":"5","author":"Jin","year":"2004","journal-title":"J. Zhejiang Univ., Sci."},{"key":"2026090206302541600_cit19","doi-asserted-by":"crossref","first-page":"2730","DOI":"10.1128\/AEM.65.6.2730-2737.1999","article-title":"Modulation of lipid metabolism and\nspiramycin biosynthesis\nin Streptomyces ambofaciens unstable mutants","volume":"65","author":"Schauner","year":"1999","journal-title":"Appl. Environ. Microbiol."},{"key":"2026090206302541600_cit20","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0087607","article-title":"A single Sfp-type phosphopantetheinyl\ntransferase plays a major role in the biosynthesis of PKS and NRPS\nderived metabolites in Streptomyces ambofaciens ATCC23877","volume":"9","author":"Bunet","year":"2014","journal-title":"PLoS One"},{"key":"2026090206302541600_cit21","doi-asserted-by":"publisher","first-page":"891","DOI":"10.1007\/s10529-007-9613-1","article-title":"In vivo functions\nof the \u03b3-butyrolactone autoregulator receptor in Streptomyces\nambofaciens producing spiramycin","volume":"30","author":"Choi","year":"2008","journal-title":"Biotechnol.\nLett."},{"key":"2026090206302541600_cit22","doi-asserted-by":"publisher","first-page":"5813","DOI":"10.1128\/jb.00712-10","article-title":"Regulation\nof the biosynthesis of the macrolide antibiotic spiramycin in Streptomyces\nambofaciens","volume":"192","author":"Karray","year":"2010","journal-title":"J. Bacteriol."},{"key":"2026090206302541600_cit23","doi-asserted-by":"publisher","first-page":"835","DOI":"10.3389\/fmicb.2017.00835","article-title":"Time-resolved\ntranscriptomics and constraint-based modeling identify system-level\nmetabolic features and overexpression targets to increase spiramycin\nproduction in Streptomyces ambofaciens","volume":"8","author":"Fondi","year":"2017","journal-title":"Front.\nMicrobiol."},{"key":"2026090206302541600_cit24","doi-asserted-by":"publisher","first-page":"167","DOI":"10.1016\/j.ijpharm.2012.06.055","article-title":"Cyclodextrins","volume":"453","author":"Kurkov","year":"2013","journal-title":"Int. J. 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Photobiol., A"},{"key":"2026090206302541600_cit27","doi-asserted-by":"publisher","first-page":"2244","DOI":"10.1002\/marc.200700505","article-title":"Novel Anti-Microbial\nHost-Guest Complexes\nBased on Cationic \u03b2-Cyclodextrin Polymers and Triclosan\/Butylparaben","volume":"28","author":"Guan","year":"2007","journal-title":"Macromol. Rapid Commun."},{"key":"2026090206302541600_cit28","doi-asserted-by":"publisher","first-page":"450","DOI":"10.1002\/jssc.201500927","article-title":"Recovery and separation of erythromycin from industrial wastewater\nby imprinted magnetic nanoparticles that exploit \u03b2-Cyclodextrin\nas the functional monomer","volume":"39","author":"Zhang","year":"2016","journal-title":"J. Sep. 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Sci."},{"key":"2026090206302541600_cit39","doi-asserted-by":"publisher","first-page":"35764","DOI":"10.1038\/srep35764","article-title":"Study to explore the mechanism to\nform inclusion complexes of \u03b2-cyclodextrin with vitamin molecules","volume":"6","author":"Saha","year":"2016","journal-title":"Sci. Rep."},{"key":"2026090206302541600_cit40","doi-asserted-by":"publisher","first-page":"509","DOI":"10.1016\/s0076-6879(82)87029-8","article-title":"Determination\nof binding stoichiometry by the continuous variation method: the Job\nplot","volume":"87","author":"Huang","year":"1982","journal-title":"Methods Enzymol."},{"key":"2026090206302541600_cit41","doi-asserted-by":"publisher","first-page":"832","DOI":"10.1111\/j.2042-7158.2012.01492.x","article-title":"Non-inclusion complexes between riboflavin\nand cyclodextrins","volume":"64","author":"de Jesus","year":"2012","journal-title":"J. Pharm. 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Drug Discovery"},{"key":"2026090206302541600_cit48","first-page":"139","article-title":"Cyclodextrins: application in different\nroutes of drug administration","volume":"55","author":"Shimpi","year":"2005","journal-title":"Acta Pharm."},{"key":"2026090206302541600_cit49","doi-asserted-by":"publisher","first-page":"535","DOI":"10.1016\/j.jpba.2008.02.006","article-title":"Effect of \u03b2-cyclodextrin\nand hydroxypropyl \u03b2-cyclodextrin complexation on physicochemical\nproperties and antimicrobial activity of cefdinir","volume":"47","author":"Aleem","year":"2008","journal-title":"J. Pharm. Biomed. Anal."},{"key":"2026090206302541600_cit50","doi-asserted-by":"publisher","first-page":"24","DOI":"10.1016\/j.ejpb.2015.10.013","article-title":"\u03b2-Cyclodextrin complexation\nas an effective drug delivery system for meropenem","volume":"99","author":"Paczkowska","year":"2016","journal-title":"Eur. J. Pharm. 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