Untitled

Caira, Mino R.; Vries, Elise de; Nassimbeni, Luigi R.; Jacewicz, Victor W.

doi:10.1023/a:1025622809025

Cited by 14 publications

(50 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1994; Rontoyianni & Mavridis, 1996;Makedonopoulou et al, 1998Makedonopoulou et al, , 1999Makedonopoulou & Mavridis, 2000, 2001, or polar groups with an intermediate tendency to be hydrated favor IM packing. It seems that the latter is true for the SC mode, as shown from the complexes crystallized in SC (Hamilton & Chen, 1988a,b;Caira et al, 1996Caira et al, , 2002Brett et al, 1999;Sanchez-Ruiz et al, 1999). However, it is dif®cult to deduce some clear relation between guest nature and the IM and SC packing modes.…”

Section: Figurementioning

confidence: 98%

“…(i) In the CD/paroxetin complex (Caira et al, 2002) the lateral displacement between dimers in adjacent layers is more than 6 A Ê (ii) In the CD/adamantanone complex (Sanchez-Ruiz et al, 1999) the corresponding displacement is even larger, close to that of the CB mode. In both cases this difference is due to the location of the dimers with respect to the 2 1 axis parallel to the unique axis b and it has been attributed to the host/guest ratio (Caira et al, 2002). In the CD/ paroxetin complex the host/guest ratio is 2:1 and in CD/adamantanone it is 2:2 nominally, but the guest is disordered, distributed over three positions.…”

Section: Figurementioning

confidence: 99%

See 1 more Smart Citation

Molecular structures of the inclusion complexes β-cyclodextrin–1,2-bis(4-aminophenyl)ethane and β-cyclodextrin–4,4′-diaminobiphenyl; packing of dimeric β-cyclodextrin inclusion complexes

Giastas

Yannakopoulou

Mavridis

2003

Acta Crystallogr B Struct Sci

View full text Add to dashboard Cite

The present investigation is part of an ongoing study on the influence of the long end-functonalized guest molecules DBA and BNZ in the crystal packing of beta-cyclodextrin (betaCD) dimeric complexes. The title compounds are 2:2 host:guest complexes showing limited host-guest hydrogen bonding at the primary faces of the betaCD dimers. Within the betaCD cavity the guests exhibit mutual pi...pi interactions and between betaCD dimers perpendicular NH...pi interactions. The DBA guest molecule exhibits one extended and two bent conformations in the complex. The BNZ guest molecule is not planar inside betaCD, in contrast to the structure of BNZ itself, which indicates that the cavity isolates the molecules and forbids the pi...pi stacking of the aromatic rings. NMR spectroscopy studies show that in aqueous solution both DBA and BNZ form strong complexes that have 1:1 stoichiometry and structures similar to the solid state ones. The relative packing of the dimers is the same in both complexes. The axes of two adjacent dimers form an angle close to 20 degrees and have a lateral displacement approximately 2.45 A, both of which characterize the screw-channel mode of packing. Although the betaCD/BNZ complex indeed crystallizes in a space group characterizing the latter mode, the betaCD/DBA complex crystallizes in a space group with novel dimensions not resembling any of the packing modes reported so far. The new lattice is attributed to the three conformations exhibited by the guest in the crystals. However, this lattice can be transformed into another, which is isostructural to that of the betaCD/BNZ inclusion complex, if the conformation of the guest is not taken into account.

show abstract

Section: Figurementioning

confidence: 98%

Section: Figurementioning

confidence: 99%

Molecular structures of the inclusion complexes β-cyclodextrin–1,2-bis(4-aminophenyl)ethane and β-cyclodextrin–4,4′-diaminobiphenyl; packing of dimeric β-cyclodextrin inclusion complexes

Giastas

Yannakopoulou

Mavridis

2003

Acta Crystallogr B Struct Sci

View full text Add to dashboard Cite

show abstract

“…Nevertheless, the crystal structure of the methylparaben/-CD complex has recently been published. This complex crystallizes in two different space groups, P1 and C2 (Caira, de Vries, Nassimbeni & Jacewicz, 2003), and is the first CD complex to exhibit polymorphism.…”

Section: Cpa/tmbcdmentioning

confidence: 99%

Inclusion compounds of plant growth regulators in cyclodextrins. V. 4-Chlorophenoxyacetic acid encapsulated in β-cyclodextrin and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin

Tsorteki

Bethanis

Pinotsis

et al. 2005

Acta Crystallogr Sect B

View full text Add to dashboard Cite

The crystal structures of 4-chlorophenoxyacetic acid (4CPA) included in beta-cyclodextrin (beta-CD) and heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin (TMbetaCD) have been studied by X-ray diffraction. The 4CPA/beta-CD complex crystallizes as a head-to-head dimer in the space group C2 in the Tetrad packing mode. The packing modes of some beta-CD dimeric complexes, having unique stackings, are also discussed. The 4CPA/TMbetaCD inclusion complex crystallizes in the space group P2(1) and its asymmetric unit contains two crystallographically independent complexes, complex A and complex B, exhibiting different conformations. The host molecule of complex A is significantly distorted, as a glucosidic residue rotated about the O4'-C1 and C4-O4 bonds forms an aperture where the guest molecule is accommodated. The phenyl moiety of the guest molecule of complex B is nearly perpendicular to the mean plane of the O4n atoms. The conformations of the guest molecules of the two complexes are similar. The crystal packing consists of antiparallel columns as in the majority of the TMbetaCD complexes published so far.

show abstract

“…The ability to effectively model cyclodextrin complexes is important given that relatively few X‐ray structures are known. When structures are available as for paroxetine 11 , they reveal a beautiful symmetrical and 1:2 arrangement effectively shielding the hydrophobic paroxetine from the aqueous medium (Figure ). Unlike calixarenes and tetrapyrroles, cyclodextrin macrocycles are notably water soluble making them suitable for use as formulation components as well as scaffolds.…”

Section: Comparison Of Lipinski Ro5 With Ppi Inhibitors and Macrocyclmentioning

confidence: 99%

Macrocycles, the edge of drug‐likeness chemical space or Goldilocks zone?

Selwood

2017

Chem Biol Drug Des

View full text Add to dashboard Cite

Untitled

Cited by 14 publications

References 10 publications

Molecular structures of the inclusion complexes β-cyclodextrin–1,2-bis(4-aminophenyl)ethane and β-cyclodextrin–4,4′-diaminobiphenyl; packing of dimeric β-cyclodextrin inclusion complexes

Molecular structures of the inclusion complexes β-cyclodextrin–1,2-bis(4-aminophenyl)ethane and β-cyclodextrin–4,4′-diaminobiphenyl; packing of dimeric β-cyclodextrin inclusion complexes

Inclusion compounds of plant growth regulators in cyclodextrins. V. 4-Chlorophenoxyacetic acid encapsulated in β-cyclodextrin and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin

Macrocycles, the edge of drug‐likeness chemical space or Goldilocks zone?

Contact Info

Product

Resources

About