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(Referência obtida automaticamente do Web of Science, por meio da informação sobre o financiamento pela FAPESP e o número do processo correspondente, incluída na publicação pelos autores.)

Quasi-enantiomeric single-nucleoside and quasi-racemic two-nucleoside hydrochloride salts and ruthenium complexes of cytidine and 2 `,3 `-dideoxycytidine analogs unveiling the negligible structure-driving role of the 2 `,3 `-moieties

Texto completo
Autor(es):
Martins, Felipe Terra [1] ; Correa, Rodrigo S. [2] ; Batista, Alzir Azevedo [2] ; Ellena, Javier [3]
Número total de Autores: 4
Afiliação do(s) autor(es):
[1] Univ Fed Goias, Inst Quim, BR-74001970 Goiania, Go - Brazil
[2] Univ Fed Sao Carlos UFSCar, Dept Quim, BR-13561901 Sao Carlos, SP - Brazil
[3] Univ Sao Paulo, Inst Fis Sao Carlos, Dept Fis Ciencia Interdisciplinar FCI, BR-13560970 Sao Carlos, SP - Brazil
Número total de Afiliações: 3
Tipo de documento: Artigo Científico
Fonte: CrystEngComm; v. 16, n. 30, p. 7013-7022, 2014.
Citações Web of Science: 9
Resumo

Insights into the structural basis of nucleoside molecular organization have been achieved from crystal engineering research. Here, we have investigated the role of differences at the 3'-position of the five-membered ring in the determination of the molecular conformation and crystal packing of quasi-enantiomeric cytidine-based nucleosides. Firstly, a hydrochloride salt of zalcitabine (2',3'-dideoxycytidine) isostructural to lamivudine (2',3'-dideoxy-3'-thiacytidine) hydrochloride was prepared. The R1/2(6) motif responsible for pairing between nucleosides and counterions as well as the assembly of chains and sheets with 2(1)-screw axis symmetry-related ionic pairs were observed in both salts, even with lamivudine differing from zalcitabine in the opposite chirality of their C1' and C4' carbons and for a sulfur atom at the 3'-position rather than a methylene group. Based on the isostructurality between zalcitabine hydrochloride and lamivudine hydrochloride, but with crystal structures which are quasi-enantiomeric, a hydrochloride salt having both nucleosides in a single crystal form was designed in this study. The obtained hybrid structure is a quasi-racemate in which chains assembled with R1/2(6)-paired lamivudine and chloride can be related by pseudo inversion symmetry to that of zalcitabine and chloride but with an antiparallel growth direction. In addition, the first examples of ruthenium(II) coordination complexes with cytidine nucleosides are reported here. The trans-bis-(triphenylphosphine)(lamivudinate)(2,2'-bipyridine) ruthenium(II) perchlorate and trans-bis-(triphenylphosphine)(cytidinate)(2,2'-bipyridine) ruthenium(II) perchlorate complexes have the same coordination geometry and similar chains made up of complex units intercalated by water despite major molecular difference given by 2'-CH2 and 3'-S moieties in lamivudinate rather than CH2OH ones in both positions of cytidinate. (AU)

Processo FAPESP: 09/08131-1 - Complexos de rutênio com ligantes de interesse biológico: aspectos químicos, estruturais e avaliação de suas citotoxicidades em células tumorais
Beneficiário:Rodrigo de Souza Corrêa
Linha de fomento: Bolsas no Brasil - Doutorado
Processo FAPESP: 13/26559-4 - Modificações estruturais em complexos de Ru(II) biologicamente ativos para o desenho de novos candidatos a metalofármacos
Beneficiário:Rodrigo de Souza Corrêa
Linha de fomento: Bolsas no Brasil - Pós-Doutorado