{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,26]],"date-time":"2026-03-26T15:09:54Z","timestamp":1774537794732,"version":"3.50.1"},"reference-count":28,"publisher":"Wiley","issue":"14","license":[{"start":{"date-parts":[[2005,4,28]],"date-time":"2005-04-28T00:00:00Z","timestamp":1114646400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2005,7,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:italic>cis<\/jats:italic>\u2010[PtCl(OH<jats:sub>2<\/jats:sub>)(NH<jats:sub>3<\/jats:sub>)<jats:sub>2<\/jats:sub>]<jats:sup>+<\/jats:sup>, the monoactivated form of cisplatin, reacts with the cyano ligand of cobalt in vitamin B<jats:sub>12<\/jats:sub> (cyanocobalamin) to form a Co\uf8ffC\uf8fdN\uf8ffPt conjugate (<jats:bold>1<\/jats:bold>). Compound <jats:bold>1<\/jats:bold> is prepared in good yield directly in aqueous solution. The remaining chloride ligand of Pt<jats:sup>II<\/jats:sup> is labile. It hydrolyzes slowly in aqueous solution and can be exchanged by stronger coordinating ligands, such as 9\u2010methylguanine or 2\u2032\u2010deoxyguanosine, to yield vitamin B<jats:sub>12<\/jats:sub>\u2013nucleobase conjugates. X\u2010ray structures of the vitamin B<jats:sub>12<\/jats:sub>\u2013cisplatin conjugate <jats:bold>1<\/jats:bold> as well as of the product with coordinated 9\u2010methylguanine (<jats:bold>2<\/jats:bold>) are presented. The coordination geometry at Pt<jats:sup>II<\/jats:sup> is almost perfectly square\u2010planar. The structure of the cobalamin compound remains essentially unchanged when compared with the original B<jats:sub>12<\/jats:sub> structure. The guanine moiety of compound <jats:bold>2<\/jats:bold> binds in a 45\u00b0 angle to the cisplatin molecule and interacts with neighboring molecules by means of \u03c0 stacking and hydrogen bonds.<\/jats:p>","DOI":"10.1002\/chem.200500117","type":"journal-article","created":{"date-parts":[[2005,4,28]],"date-time":"2005-04-28T09:51:24Z","timestamp":1114681884000},"page":"4089-4095","source":"Crossref","is-referenced-by-count":53,"title":["Cyanide\u2010Bridged Vitamin B<sub>12<\/sub>\u2013Cisplatin Conjugates"],"prefix":"10.1002","volume":"11","author":[{"given":"Stefan","family":"Mundwiler","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Bernhard","family":"Spingler","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Philipp","family":"Kurz","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Susanne","family":"Kunze","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Roger","family":"Alberto","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2005,6,24]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783906390420"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0163-7258(99)00018-2"},{"key":"e_1_2_6_3_2","volume-title":"Vitamin B12 and B12\u2010Proteins","year":"1998"},{"key":"e_1_2_6_4_2","volume-title":"Chemistry and Biochemistry of B12","year":"1999"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.4065\/75.6.568"},{"key":"e_1_2_6_6_2","unstructured":"C. B.Grissom F. G.West W. A.Howard Jr. U.S. Pat. 6315978 2001."},{"key":"e_1_2_6_7_2","doi-asserted-by":"crossref","first-page":"556","DOI":"10.1096\/fj.00-0446fje","volume":"15","author":"Cannon M. J.","year":"2001","journal-title":"FASEB J."},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol006825v"},{"key":"e_1_2_6_9_2","unstructured":"S.Wilson K. S.Reinhard X.Gao U.S. Pat. Appl. 2004047917 2004."},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00818a018"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/c29710000850"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/dt9830001929"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1991.tb16124.x"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/bc970003"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi002145o"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M102510200"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M405449200"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1074-5521(02)00224-7"},{"key":"e_1_2_6_19_2","unstructured":"H. Kunkely V. Pawloski A. Vogler 14th Conference on Coordination Chemistry Smolenice Slovakia 1993 363\u2013366."},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200460923"},{"key":"e_1_2_6_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200460923"},{"key":"e_1_2_6_21_2","volume-title":"Infrared and Raman Spectra of Inorganic and Coordination Compounds","author":"Nakamoto K.","year":"1978"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00175a020"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic981384l"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja017588"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889898007717"},{"key":"e_1_2_6_26_2","unstructured":"G. M. Sheldrick SHELXL97\u20102 Program for the Refinement of Crystal Structures University of G\u00f6ttingen Germany 1997."},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889897003117"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200500117","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200500117","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T13:14:48Z","timestamp":1760274888000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200500117"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2005,6,24]]},"references-count":28,"journal-issue":{"issue":"14","published-print":{"date-parts":[[2005,7,4]]}},"alternative-id":["10.1002\/chem.200500117"],"URL":"https:\/\/doi.org\/10.1002\/chem.200500117","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2005,6,24]]}}}