| Full text | |
| Author(s): |
Total Authors: 3
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| Affiliation: | [1] Univ Sao Paulo, Inst Fis Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil
[2] Univ Fed Alfenas, Dept Ciencias Exatas, BR-37130000 Alfenas, MG - Brazil
Total Affiliations: 2
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| Document type: | Journal article |
| Source: | Crystal Growth & Design; v. 10, n. 2, p. 676-684, FEB 2010. |
| Web of Science Citations: | 21 |
| Abstract | |
A DNA-like duplex of nucleosides is probable to exist even without the 5'-phosphate groups needed to assemble the chain backbone. However, double-stranded helical structures of nucleosides are unknown. Here, we report a duplex of nucleoside analogs that is spontaneously assembled due to stacking of the neutral and protonated molecules of lamivudine, a nucleoside reverse transcriptase inhibitor (NTRI) widely used in anti-HIV drug combinatory medication. The left-handed lamivudine duplex has features similar to those of i-motif DNA, as the face-to-face base stacking and the helix rise per base pair. Furthermore, the protonation pattern on alternate bases expected for it DNA-like duplex stabilized by pairing of neutral and protonated cytosine fragments was observed for the first time in the lamivudine double-stranded helix. This structure demonstrates that hydrogen bonds can substitute for covalent phosphodiester linkage in the stabilization of the duplex backbone. This interesting example of spontaneous molecular self-organization indicates that the 5'-phosphate group could not be a requirement for duplex assembly. (AU) | |
| FAPESP's process: | 07/07185-5 - Screening, characterization and evaluation for novel crystal forms from antiretroviral and antineoplastic drugs |
| Grantee: | Felipe Terra Martins |
| Support Opportunities: | Scholarships in Brazil - Doctorate |