91026-01-6Relevant academic research and scientific papers
The spermine-bisaryl conjugate as a potent inducer of B- to Z-DNA transition
Doi, Issei,Tsuji, Genichiro,Kawakami, Kyoko,Nakagawa, Osamu,Taniguchi, Yosuke,Sasaki, Shigeki
experimental part, p. 11993 - 11999 (2011/01/12)
DNA containing alternating purine and pyrimidine repeats has the potential to adopt the Z-DNA structure, one of the well-studied structures besides A- and B-DNA. Despite a number of molecular models that have been proposed to explain the mechanism for B→Z transition, there is continued discussion on the mechanism and physiological role of this transition. In this study, we have found that the bis(2-naphthyl)-maleimide-spermine conjugate (3c) exhibits a remarkable ability to cause the B→Z transition of d(CGCGCG)2 at low salt concentrations. Using isothermal titration calorimetry (ITC) we show that the B→Z transition induced by 3c is both enthalpically and entropically favorable. The ligand might effect the dehydration of B-DNA, which leads to the B→Z transition. Interestingly, an intermediate CD between the B and Z forms was observed in the pH-dependent transition in the presence of the ligand. The unique structure and characteristics of the ligand designed in this investigation will be useful for the study of Z-DNA. From B to Z: The bis(2-naphthyl)maleimide-spermine conjugate shown in the figure exhibits a remarkable ability to cause the B→Z transition of d(CGCGCG)2 at low salt concentrations. A stable intermediate between the B and Z forms was observed in the presence of the ligand at about pH 8.
Bifunctional maleimide dyes as selective anion sensors
Lin, Zhenghuan,Chen, Hung Cheng,Sun, Shih-Sheng,Hsu, Chao-Ping,Chow, Tahsin J.
experimental part, p. 5216 - 5221 (2009/11/30)
A class of disubstituted maleimide dyes with two symmetrical NH binding sites was found to exhibit distinct color change and fluorescence quenching effect for fluoride, cyanide, and dihydrogen phosphate anions. The intense red emission displayed apparent
Synthesis of indolo[2,3-a]pyrrolo[3,4-c]carbazoles by oxidative cyclization of bisindolylmaleimides with a rhodium(III)-copper(II) catalytic system
Witulski, Bernhard,Schweikert, Torsten
, p. 1959 - 1966 (2007/10/03)
A novel catalytic protocol for the synthesis of a series of indolo[2,3-a]pyrrplo[3,4-c]carbazoles based on the bimetallic system RhCl 3·3H2O and Cu(OAc)2·H 2O in the presence of molecular oxygen was investigated
Evaluation of alternative approaches for the synthesis of macrocyclic bisindolylmaleimides
Bartlett, Stephen,Nelson, Adam
, p. 2874 - 2883 (2007/10/03)
Approaches for the synthesis of macrocyclic bisindolylmaleimides, in which the indole nitrogens are linked with a tether, are described. Two alternative approaches were investigated: macrocyclisation in either the southern (by adding the tether to the bisindolylmaleimide ring system) or the northern district. With two-, three-and four-atom tethers, both of these approaches were unsuccessful for a wide range of attempted macrocyclisation reactions (palladium-catalysed π-allyl substitution, ring-closing metathesis, McMurry reaction, iodocyclisation, formation of a silylene derivative, substitution of an α,ω-disubstituted electrophile). The failure of all of these reactions was ascribed to the strained nature of the target ring system. However, with longer tethers (six to ten atoms), the macrocycles could prepared using either a ring-closing metathesis reaction or by substitution of an α,ω-dibromide). Fourteen successful macrocyclisation reactions are described; deprotection gave eleven macrocyclic bisindolylmaleimides in which an imide substituent had been removed.
Pyrrole derivatives and cell death inhibitors
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, (2008/06/13)
Bisindolylpyrrole derivatives represented by general formula [I] which are useful in inhibiting cell death and expected as being useful as preventives and remedies for the progress of various diseases in the progress and worsening of which cell death part
Coupling reactions of indole-3-acetic acid derivatives. Synthesis of arcyriaflavin A
Bergman, Jan,Koch, Eva,Pelcman, Benjamin
, p. 2609 - 2614 (2007/10/03)
The bisindolesuccinic acid methyl ester 10 was obtained by an iodine-promoted coupling of the dianion 9. The diester was converted to the N-benzylimide 12, which was oxidatively cyclized to the indolo[2,3-a]pyrrolo[3,4-c]-carbazole 15. The diester 10 coul
Acid-induced dimerization of 3-(1H-indol-3-yl)maleimides. Formation of cyclopentindole derivatives
Bergman, Jan,Janosik, Tomasz,Koch, Eva,Pelcman, Benjamin
, p. 2615 - 2621 (2007/10/03)
Acid-induced dimerizations of 3-substituted maleimides have been investigated, leading to e.g. the cyclopentindole 9 and the deeply coloured spiro compounds 24 and 25 in good yields. 3-(1H-Indol-3-yl)maleimide 6b readily gave the cycloaddition products 13
A facile synthesis of staurosporine aglycone
Xie, Guojian,Lown, J. William
, p. 5555 - 5558 (2007/10/02)
A highly efficient method is described for the synthesis of staurosporine aglycone 3 from the readily available dibromomaleic acid in six steps.
COUPLING OF INDOLEACETIC ACID TRIANION OR METHYL INDOLEACETIC ACID DIANION. A BIOMIMETIC APPROACH TO INDOLOCARBAZOLE ALKALOIDS.
Bergman, J.,Pelcman, B.
, p. 4441 - 4444 (2007/10/02)
The bisindolesuccinic acid ester 8b was obtained as a mixture of diastereomers by iodine promoted coupling of the dianion 7b or via the trianion 7a.The diester was converted to the N-benzylimide 10 which was oxidatively cyclized to the indolopyrrol
