Toward supramolecular architectures of the anti-HIV drug lamivudine: understanding the effect of the inclusion of water in a hydrochloride form

Abstract

Two salts of the anti-HIV drug lamivudine, namely, lamivudine hydrochloride and lamivudine hydrochloride monohydrate, were prepared for the first time. Structural relationships and the role of water in crystal assembly and lamivudine conformation were established and allowed for a rational approach to understand how solid state properties could be changed by engineering new salts of the drug.

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

“…12 Based on the isostructurality of the anhydrous forms of lamivudine and zalcitabine 11 crystallizing in the enantiomorphic tetragonal space groups P4 3 2 1 2 and P4 1 2 1 2, respectively, we were interested in knowing whether both APIs could crystallize together in a multicomponent salt. In fact, lamivudine and zalcitabine are 2′,3′-dideoxycytidine analogs differing in a sulfur atom at 3′-position in the first rather than a methylene group in the last and in the chirality of their asymmetry centers.…”

“…For this purpose, and based on the known synthetic route of lamivudine hydrochloride (1), 12 a hydrochloride salt of zalcitabine was prepared. Zalcitabine hydrochloride (2) is isostructural to 1.…”

Vibrational and thermal analyses of multicomponent crystal forms of the anti-HIV drugs lamivudine and zalcitabine

“…On the other hand, the hydroxyl oxygen is oriented on the same side of 3 -S in 1 rather than one methylene hydrogen as occurs in 2 (Fig. 4) [8]. In turn, a methylene hydrogen points toward the aromatic C6 H6 moiety in 1. assigned to out-of-plane C H angular deformation, carbonyl stretching of hydrogen maleate and lamivudine, and to C6 H6 stretching, respectively.…”

“…In case of 4, maleic acid was directly dissolved into the solution of lamivudine in isopropyl alcohol instead. Full details of synthesis and crystal structure determination of the five salts can be found in four related papers [5,8,13,14]. Before thermal and vibrational studies, authenticity and purity of each crystal form were first checked by X-ray powder diffraction (XRPD) technique using CuK␣ radiation ( = 0.15418 nm) generated at 40 kV and 30 mA on a Shimadzu XRD-6000 Bragg-Brentano geometry diffractometer (Kratos Analytical Inc., NY).…”

One-Pot Synthesis, Crystal Structures and Thermal Properties of Two Three-Dimensional Cobalt(II) Complexes

“…[1][2][3][4][5][6][7][8][9] It is widely acknowledged that the coordinative bonding is the primary interaction to sustain the network, while supramolecular interactions, such as hydrogen bonding, π-π stacking interactions and Van der Waals forces are also believed to play important roles. [10][11][12][13][14][15][16][17] To date, a variety of supramolecular polymers with complicated architectures and interesting properties based on different bridging ligands especially aromatic polycarboxylate ligands have been synthesized successfully.…”