X-ray crystal structures of two solvent complexes involving positionally isomeric 9,10-anthraquinonecarboxylic acids and DMSO

Gruber, Tobias; Helas, Stefanie F.; Seichter, Wilhelm; Weber, Edwin

doi:10.1007/s11224-010-9648-0

Cited by 7 publications

(5 citation statements)

References 15 publications

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“…6). Longitudinal structures of DMSO-DMSO associations were also observed in crystal structures of two solvents of 9,10-anthraquinonecarboxylic acids and DMSO [22], however the dipole-dipole interaction was not stated.…”

Section: X-ray Crystal Structurementioning

confidence: 90%

X-Ray Crystal Structure of Betulin–DMSO Solvate

Boryczka¹,

Michalik²,

Jastrzębska

et al. 2011

J Chem Crystallogr

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Betulin is a lupane triterpenoid [lup-20(29)-ene3b,28-diol, C 30 H 50 O 2 ] showing high biological activity. This activity is supposed to be strongly affected by the molecular structure of its polymorphic forms. Different solvate polymorphic forms of betulin have aroused increasing interest as the possible anticancer agents of natural origin. X-ray diffraction was used to investigate crystal structure of (1:1) betulin-DMSO solvate. Title compound crystallizes in the orthorhombic P2 1 2 1 2 1 space group. Unit cell parameters are as follows: a = 7.0006(2) Å , b = 12.1623(3) Å , c = 33.6991(8) Å , Z = 4. Crystal packing and selected geometric parameters are described. It has been found that the hydrogen bonding and the dipole-dipole interaction between DMSO molecules play the major role in the formation of the crystal structure.

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Section: X-ray Crystal Structurementioning

confidence: 90%

X-Ray Crystal Structure of Betulin–DMSO Solvate

Boryczka¹,

Michalik²,

Jastrzębska

et al. 2011

J Chem Crystallogr

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“…Among different binding models, only the 1:1 model fits the chemical shift of proton 1 with K 11 = (3.51 ± 0.02) × 10 –5 M –1 and a positive Δ G bind , showing that the formation of CAF-BA aggregates is thermodynamically not favored. It has been reported that compounds with carboxylic acid interact strongly with DMSO as a strong hydrogen bond acceptor. − Hence, in the competition between CAF, BA, and DMSO, BA and DMSO are likely more easy to form interactions and there is little complexation of CAF and BA in the solution.…”

Section: Resultsmentioning

confidence: 99%

Using Prenucleation Aggregation of Caffeine-Benzoic Acid as a Rapid Indication of Co-crystallization from Solutions

et al. 2023

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Co-crystal design is a convenient way to remedy the poor biopharmaceutical properties of drugs. Most studies focus on experimental co-crystal screening or computational prediction, but hardly any work has been done toward fast, efficient, and reliable prediction of solution crystallization for co-crystal formation. Here, we study the caffeine-benzoic acid co-crystal system, due to its reported difficulty to crystallize from the solution phase. With this work, we investigate whether there is a link between prenucleation aggregation in solution and co-crystal formation and how to harness this for crystallization prediction. 1 H and 13 C NMR spectroscopy is used to study the prenucleation interaction between caffeine and benzoic acid in methanol, acetone, and acetonitrile as examples of common solvents. In this system, crystallization from methanol leads to no co-crystallization, from acetone to concomitant crystallization of co-crystal and caffeine, and from acetonitrile to pure co-crystal formation from solution. Strong heteromeric dimers were found to exist in all three solvents. Ternary phase diagrams were defined and a solution-accessible co-crystal region was found for all solvents. For this system, the prenucleation clusters found in solution could be linked to the crystallization of the co-crystal. Crystallization from DMSO did not yield the co-crystal and there were no detectable prenucleation aggregates. NMR spectroscopy to probe dimers in solution can thus be used as a fast, reliable, and promising tool to predict co-crystallization from specific solvents and to screen for suitable solvents for manufacturing and scale-up.

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“…Anthraquinones are highly effective chemotherapeutic agents with a wide spectrum of antitumor activity, see: Unverferth et al (1983); Kantrowitz & Bristow (1984); Stuart et al (1984); Arcamone (1987). For related compounds, see: Bruijnincx & Sadler (2008); Gruber et al (2010); Neufeind et al (2011…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of tetraaquabis(8-chloro-9,10-dioxo-9,10-dihydroanthracene-1-carboxylato-κO¹)cobalt(II) dihydrate

Cai

Liu

et al. 2014

Acta Cryst E

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In the title complex, [Co(C 15 H 6 ClO 4 ) 2 (H 2 O) 4 ]Á2H 2 O, the Co II ion is bound by two carboxylate O atoms of two 5-chloro-9,10-anthraquinone-1-carboxylate anions and four water O atoms in a trans conformation, forming an irregular octahedral coordination geometry. This arrangement is stabilized by intramolecular O-HÁ Á ÁO hydrogen bonds between water and carboxylate. Further O-HÁ Á ÁO hydrogen bonds between coordinating and non-coordinating water and carboxylate produce layers of molecules that extend parallel to (001). The organic ligands project above and below the plane. Those ligands of adjacent planes are interdigitated and there areinteractions between them with centroid-centroid distances of 3.552 (2) and 3.767 (2) Å that generate a three-dimensional supramolecular structure.

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X-ray crystal structures of two solvent complexes involving positionally isomeric 9,10-anthraquinonecarboxylic acids and DMSO

Cited by 7 publications

References 15 publications

X-Ray Crystal Structure of Betulin–DMSO Solvate

X-Ray Crystal Structure of Betulin–DMSO Solvate

Using Prenucleation Aggregation of Caffeine-Benzoic Acid as a Rapid Indication of Co-crystallization from Solutions

Crystal structure of tetraaquabis(8-chloro-9,10-dioxo-9,10-dihydroanthracene-1-carboxylato-κO¹)cobalt(II) dihydrate

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X-ray crystal structures of two solvent complexes involving positionally isomeric 9,10-anthraquinonecarboxylic acids and DMSO

Cited by 7 publications

References 15 publications

X-Ray Crystal Structure of Betulin–DMSO Solvate

X-Ray Crystal Structure of Betulin–DMSO Solvate

Using Prenucleation Aggregation of Caffeine-Benzoic Acid as a Rapid Indication of Co-crystallization from Solutions

Crystal structure of tetraaquabis(8-chloro-9,10-dioxo-9,10-dihydroanthracene-1-carboxylato-κO1)cobalt(II) dihydrate

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Crystal structure of tetraaquabis(8-chloro-9,10-dioxo-9,10-dihydroanthracene-1-carboxylato-κO¹)cobalt(II) dihydrate