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Cyanide-bridged vitamin B12-cisplatin conjugates.


Mundwiler, S; Spingler, B; Kurz, P; Kunze, S; Alberto, R (2005). Cyanide-bridged vitamin B12-cisplatin conjugates. Chemistry - A European Journal, 11(14):4089-4095.

Abstract

cis-[PtCl(OH(2))(NH(3))(2)](+), the monoactivated form of cisplatin, reacts with the cyano ligand of cobalt in vitamin B(12) (cyanocobalamin) to form a Co-C[triple chemical bond]N-Pt conjugate (1). Compound 1 is prepared in good yield directly in aqueous solution. The remaining chloride ligand of Pt(II) is labile. It hydrolyzes slowly in aqueous solution and can be exchanged by stronger coordinating ligands, such as 9-methylguanine or 2'-deoxyguanosine, to yield vitamin B(12)-nucleobase conjugates. X-ray structures of the vitamin B(12)-cisplatin conjugate 1 as well as of the product with coordinated 9-methylguanine (2) are presented. The coordination geometry at Pt(II) is almost perfectly square-planar. The structure of the cobalamin compound remains essentially unchanged when compared with the original B(12) structure. The guanine moiety of compound 2 binds in a 45 degrees angle to the cisplatin molecule and interacts with neighboring molecules by means of pi stacking and hydrogen bonds.

cis-[PtCl(OH(2))(NH(3))(2)](+), the monoactivated form of cisplatin, reacts with the cyano ligand of cobalt in vitamin B(12) (cyanocobalamin) to form a Co-C[triple chemical bond]N-Pt conjugate (1). Compound 1 is prepared in good yield directly in aqueous solution. The remaining chloride ligand of Pt(II) is labile. It hydrolyzes slowly in aqueous solution and can be exchanged by stronger coordinating ligands, such as 9-methylguanine or 2'-deoxyguanosine, to yield vitamin B(12)-nucleobase conjugates. X-ray structures of the vitamin B(12)-cisplatin conjugate 1 as well as of the product with coordinated 9-methylguanine (2) are presented. The coordination geometry at Pt(II) is almost perfectly square-planar. The structure of the cobalamin compound remains essentially unchanged when compared with the original B(12) structure. The guanine moiety of compound 2 binds in a 45 degrees angle to the cisplatin molecule and interacts with neighboring molecules by means of pi stacking and hydrogen bonds.

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Additional indexing

Item Type:Journal Article, refereed
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:4 July 2005
Deposited On:11 Feb 2008 12:25
Last Modified:05 Apr 2016 12:20
Publisher:Wiley-Blackwell
ISSN:0947-6539
Publisher DOI:10.1002/chem.200500117
PubMed ID:15861475

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