ChemInform Abstract: The Molecular Recognition of DNA.

Thurston, DE; Thompson, Andrew S.

doi:10.1002/chin.199049303

Cited by 8 publications

(9 citation statements)

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“…These include pyrrolo [2,1-c] [1,4]benzodiazepines (PBDs) and lexitropsins [15]. PBDs are well known naturally occurring DNA interactive antitumour antibiotics like anthramycin, chicamycin and DC-81 (3), which are produced from various Streptomyces bacteria [16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and potential cytotoxic activity of new phenanthrylphenol-pyrrolobenzodiazepines

Kamal

Sreekanth

Kumar

et al. 2010

European Journal of Medicinal Chemistry

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Section: Introductionmentioning

confidence: 99%

Synthesis and potential cytotoxic activity of new phenanthrylphenol-pyrrolobenzodiazepines

Kamal

Sreekanth

Kumar

et al. 2010

European Journal of Medicinal Chemistry

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“…In this context, PDBs are one of the most promising types of lead compounds. [8] Some derivatives possess cancerostatic and antiinfective properties [9,10] and can be used as affinitycleavage reagents in molecular biology. [11] The PBD ring system is also found in natural antitumor antibiotics such as anthramycin, [12,13,14] and many others.…”

Section: Introductionmentioning

confidence: 99%

Pyrimidine‐Annulated Pyrrolobenzodiazepines. A New Ring System Related to Aspergillus Alkaloids

et al. 2005

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Pyrrolo[2,1‐c][1,4]benzodiazepine‐5,11‐dione was converted into the corresponding C‐11‐monothiolactam and subsequently treated with amines to give cyclic amidines, which racemize due to the formation of tautomers (NMR, X‐ray analysis) under basic conditions. We treated these amidines with bis(trichlorophenyl) malonate esters. Formation of neutral tautomers of the 1,3,8‐triones of the new 4,7a,12b‐triaza‐dibenzo[e,g]azulene ring system gave a twisted molecule with both helical and chiral structure elements (NMR, X‐ray analysis), which caused a splitting of the NMR signals into two sets. Results of two X‐ray single crystal analyses are presented, together with an ab initio calculation. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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“…All of these drugs have either a well-established or a potential antitumor activity that is partially related to their binding to DNA. A very special effort is made nowadays in drug design to improve the sequence specificity of minor groove binders, with the final goal of targeting specific genes 33,[36][37][38] . Structural characterization of the complexes are generally made by crystallography 39 , NMR 40 or electric linear dichroism 41 , which are quite labour-intensive methods.…”

Section: Introductionmentioning

confidence: 99%

Interaction between antitumor drugs and a double-stranded oligonucleotide studied by electrospray ionization mass spectrometry

1999

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Electrospray ionization mass spectrometry has been used to investigate the complex formation between a double-stranded oligonucleotide and various antitumor drugs belonging to two categories: intercalators (ethidium bromide, amsacrine and ascididemin) and minor groove binders (Hoechst 33258, netropsin, distamycin A, berenil and DAPI). The goal of this study is to determine whether the relative intensities in the mass spectra reflect the relative abundances of the species in the solution phase. The full scan MS spectra suggest non-specific binding for the intercalators and specific binding for the minor groove binders. The preferential stoichiometries adopted by each minor groove binder have been determined by studying the influence of the drug concentration on the spectra. We obtained 2:1 > 1:1 for distamycin, 1:1 > 2:1 for Hoechst 33258 and DAPI, and only the 1:1 complex for netropsin and berenil. These features reflect their known behavior in solution. The compared MS/MS spectra of the 1:1 complexes with Hoechst and netropsin, when correlated to published crystallographic data, suggest the possibility to infer some structural information. The relative binding affinities of the drug for the considered duplex have been deduced with two by two competition experiments, assuming that the relative intensities reflect the composition of the solution phase. The obtained affinity scale is the following: netropsin > distamycin A > DAPI > Hoechst 33258 > berenil. These examples show some of the potential uses of mass spectrometry as a useful tool for the characterization of specific drug binding to DNA, and possibly a rapid drug screening method requiring low amounts of materials.

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ChemInform Abstract: The Molecular Recognition of DNA.

Cited by 8 publications

References 0 publications

Synthesis and potential cytotoxic activity of new phenanthrylphenol-pyrrolobenzodiazepines

Synthesis and potential cytotoxic activity of new phenanthrylphenol-pyrrolobenzodiazepines

Pyrimidine‐Annulated Pyrrolobenzodiazepines. A New Ring System Related to Aspergillus Alkaloids

Interaction between antitumor drugs and a double-stranded oligonucleotide studied by electrospray ionization mass spectrometry

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