198 Topics in Current Chemistry Editorial Board: A. de Meijere KN ...

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Directional Aspects of Intermolecular Interactions 45 b c Fig. 36 b, c. b More detailed diagram that compares the binding of methotrexate (upper diagram) and folate (lower diagram); c motif for recognition of substrate or inhibitor inferred from these crystallographic studies, together with their graph-set designations
46 J.P. Glusker 2. Non-intercalative groove binding. The drug lies in one of the grooves in DNA, following the helical contour of DNA as it binds. Netropsin and distamycin bind in this way. 3. Covalent bond formation. This occurs with mitomycin C. The anthracyclines, such as daunomycin and its hydroxy analogue, adriamycin, are naturally-occurring tetracyclic aminoglycosidic derivatives that contain an anthraquinone chromophore. The main target of these drugs appears to be DNA, probably by formation of an intercalation complex. Daunomycin and adriamycin have a planar chromophore with an amino sugar extending out of this plane. In the crystal structure of the complex of adriamycin with a self-complementary hexadeoxynucleotide, the oligonucleotide forms a right-handed helix with two molecules of adriamycin intercalated in the d(CpG) sequences at each end, as shown in Fig. 37 [93–95]. Adriamycin and daunomycin are intercalated in a similar manner with their long axes perpendicular to those of the base pairs; the 14-hydroxyl group does not significantly affect the orientations of the chromophore or the amino sugar. The hydroxyl group forms two hydrogen bonds to an adjacent guanine. The amino sugar lies in the minor groove of the distorted helix, but does not form bonds to the nucleic acid. Thus ring A anchors adriamycin in DNA, and the nucleic-acid backbone is distorted by the interactions formed. Glycosylation of C5 of a thymine residue in an oligonucleotide does not prevent intercalation [96]. Recently, a bis intercalating derivative of daunomycin has been studied [97]. In this compound the amino groups are joined by a xylyl group. This daunomy- a Fig. 37 a – c. Binding of daunomycin to an oligonucleotide [95]: a chemical formula of daunomycin, showing some interactions in the crystalline state. R 1=CH 3,R 2=CH 3 for daunomycin, CH 2OH for adriamycin
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198 Topics in Current Chemistry Edi
Page 3 and 4: Design of Organic Solids Volume Edi
Page 5 and 6: Volume Editors Prof. Dr. Edwin Webe
Page 7 and 8: VIII preface tion at an amazing lev
Page 9 and 10: Contents of Volume 196 Carbon Rich
Page 11 and 12: 2 J.P. Glusker 5 Interactions of Pl
Page 13 and 14: 4 J.P. Glusker Perturbations to the
Page 15 and 16: 6 J.P. Glusker 2.1 Sources of Cryst
Page 17 and 18: 8 J.P. Glusker other induced, will
Page 19 and 20: 10 J.P. Glusker The forces here hav
Page 21 and 22: 12 J.P. Glusker lographic structure
Page 23 and 24: 14 J.P. Glusker a c Fig. 6 a - c. D
Page 25 and 26: 16 J.P. Glusker hydrogen bond H◊
Page 27 and 28: 18 J.P. Glusker Fig. 9. Citric acid
Page 29 and 30: 20 J.P. Glusker peptide plane and a
Page 31 and 32: 22 J.P. Glusker 4.5 F◊◊◊H Int
Page 33 and 34: 24 J.P. Glusker rine-containing com
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Page 39 and 40: 30 J.P. Glusker As for carboxylate
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Hydrogen-Bonded Ribbons, Tapes and
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132 Y. Aoyama 4 Catalysis . . . . .
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134 Y. Aoyama 2.2 Symmetry-Controll
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136 Y. Aoyama A trigonal centre is
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138 Y. Aoyama 18 19 Fig. 5. 2D net
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140 Y. Aoyama 24 ded (O-H◊◊◊O
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142 Y. Aoyama 2.4 Interaction-Suppo
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144 Y. Aoyama In the presence of a
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146 Y. Aoyama clusion compounds (se
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148 Y. Aoyama are intriguing guests
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150 Y. Aoyama The tuning or enginee
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152 Y. Aoyama Fig. 16. Binding isot
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154 Y. Aoyama The desorption of the
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156 Y. Aoyama Fig. 17. Suggested me
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158 Y. Aoyama 5 Concluding Remarks
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160 Y. Aoyama 4. Hölderich W, Hess
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Crystalline Polymorphism of Organic
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Author Index Volumes 151-198 Author
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Author Index Volumes 151 - 198 2 1
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Author Index Volumes 151 - 198 213
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Author Index Volumes 151 - 198 2 ]
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Springer and the environment At Spr
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198 Topics in Current Chemistry Editorial Board: A. de Meijere KN ...

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