Conformational properties of DNA minor groove binder Hoechst 33258 in gas phase and in aqueous solution

Issar, Upasana; Kumari, Tripti; Arora, R; Kakkar, Rita

doi:10.1016/j.comptc.2017.05.006

Cited by 11 publications

(2 citation statements)

References 72 publications

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“…[1,2] H33258 consist with three parts, two asymmetrically linked benzimidazole group that attached with one phenol ring and the other part with N methylpiperazine ring as shown in Scheme 1. [3][4][5] Depending on pH, H33258 exists in different cationic form. Crescent shaped Hoechst molecules have monocationic nature at pH 7.0 with hydrogen bond donor and acceptor property.…”

Section: Introductionmentioning

confidence: 99%

“…2’‐(4‐hydroxyphenyl)‐5‐(4‐methyl‐1‐piperazinyl)‐2,5’‐bi‐1H‐benzimidazole trihydrochloride is commonly known as Hoechst 33258 (H33258) that belongs to the bis‐benzimidazole family [1,2] . H33258 consist with three parts, two asymmetrically linked benzimidazole group that attached with one phenol ring and the other part with N methylpiperazine ring as shown in Scheme 1 [3–5] . Depending on pH, H33258 exists in different cationic form.…”

Section: Introductionmentioning

confidence: 99%

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The Role of Surfactant Head Group Charge on Binding of Hoechst 33258 with Micelles

Shit,

Das,

Mandal

et al. 2024

ChemistrySelect

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Owing to the diverse biological application, photophysical behaviour of Hoechst 33258 (H33258) is an important topic in biophysical research. Here, we have reported the photophysical behavior of H33258 in model biomembrane mimicking micellar microenvironment. In order to understand the molecular mechanism of the interaction of H33258 with micelles, we have used cationic (Hexadecetyltrimethyl ammonium bromide (CTAB)), anionic (sodium dodecyl sulphate (SDS)), and non‐ionic (t‐octylphenoxypolyoxyethanol, Triton‐X100 (TX 100)) micelles. From the steady‐state emission study the evaluated apparent binding constant (Kb) values for the complex formation between H33258 and CTAB, SDS and TX 100 micelle were (1.45±0.42)×105, (31.95±4.89)×105 and (3.10±0.73)×105 M−1, respectively. Thus, it was found that the Kb value was greater in the case of anionic micelle than non‐ionic and cationic micelles. Such differences in Kb values were due to the electrostatic interaction and hydrogen bond formation between the probe molecule and micelles. In addition, time‐resolved fluorescence decay and time‐resolved fluorescence anisotropy studies were performed to understand the dynamical behavior of H33258 in presence of micelles. The interaction of H33258 with micelles might be useful to study the structure and dynamics of different bio‐membranes and to formulate new drug delivery system.

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