Electronic Spectra and Electronic Structures of Some Antimicrobials Derived from Proflavine

Naik, Datta V.; Capomacchia, Anthony C.; Roy, Timothy A.

doi:10.1002/jps.2600640619

Cited by 15 publications

(11 citation statements)

References 4 publications

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“…Protonation on the ring nitrogen of Pf and PD is calculated to lower the energy of the absorption (supplementary information 3 ), consistent with observed shifts to longer wavelength of the absorption maxima at low pH (Table 1). pK a s for Pf in aqueous solution are reported at 0.3 and 9.5, 18 and our data (supplementary information 3 ) concur. At pH 7 the dominant monocation has an S 0 A S 1 absorption maximum at 445 nm with an extinction coefficient of 41 000 M 21 cm 21 .…”

Section: Synthesis and Absorbance Of Diazido-proflavinessupporting

confidence: 86%

Synthesis and binding of proflavine diazides as functional intercalators for directed assembly on DNA

et al. 2013

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Proflavine diazide (PD) with amido-azide substituents on the amine groups and its N-methylated analogue (MePD) bind strongly to DNA by nearest-neighbour intercalation with little sequence selectivity, presenting reactive azide groups in the major groove. PD is neutral in aqueous solution but experiences binding-coupled protonation on interaction with DNA with an apparent pK a shift of 2.5 units. MePD can be click modified in situ on DNA with alkyne-functionalised thienyl-pyrrole as a precursor for conducting polymer synthesis, and remains intercalated after reaction with the substituents aligned in the groove.

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Section: Synthesis and Absorbance Of Diazido-proflavinessupporting

confidence: 86%

Synthesis and binding of proflavine diazides as functional intercalators for directed assembly on DNA

et al. 2013

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“…When amino groups are incorporated in positions 3 and 9, the protonation constant of rivanol is enhanced by six orders of magnitude in comparison with acridine (Table 1). Given this, due to the conju gation between electron pairs of the amino groups and the aromatic π electron system of acridine cycle, these groups demonstrate very weak basic properties; i.e., they are protonated only in acid solutions [9]. Thus, in the pH range of 2-8, all substituted acridines are present in solutions as cations in which protonated nitrogen atoms are located in heterocycles.…”

Section: Resultsmentioning

confidence: 98%

Adsorption complexes of acridine diaminoderivatives on silica surface

2012

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The adsorption of acridine diaminoderivatives on the surface of finely dispersed silica from aque ous solutions is studied in relation to pH, ionic strength, and adsorbate concentration. The stability constants of the surface complexes of acridine derivatives with unionized and dissociated silanol groups of silica are cal culated within the framework of the electrostatic model of surface complexation (the basic Stern model). Dimerization of all examined compounds in aqueous solutions is taken into account. It is established that, in the case of acridine dyes (orange and yellow), complexes containing both monomeric and dimeric forms of these compounds are formed on silica surface. The selection in favor of one of the possible sets of the con stants, which quantitatively characterize the equilibria of the reactions, results from the analysis of the adsorption isotherms of examined diaminoacridines.

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“…It was found that the fluorescence recovery efficiency ( F / F 0 ) reached a maximum at pH 3.5. This was probably because the amino groups of AO were almost protonated at pH 3.5 , which was conducive to the reaction between AO and PSS, resulting in the decrease in the fluorescence signal of the reagent blank ( F 0 ). Finally, pH 3.5 was chosen as the optimum pH for the detection of CTAB.…”

Section: Resultsmentioning

confidence: 99%

Sensitive and selective turn‐on fluorescence method for cetyltrimethylammonium bromide determination based on acridine orange–polystyrene sulfonate complex

Hao

Kang

et al. 2015

Luminescence

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This work proposed a rapid and novel fluorescence-sensing system using a complex of acridine orange (AO) and polystyrene sulfonate (PSS) to sensitively recognize and monitor cetyltrimethylammonium bromide (CTAB) in an aqueous medium. AO can interact with PSS and a complex is formed via electrostatic attraction and hydrophobic interaction. The fluorescence of AO is greatly quenched after the introduction of PSS. Upon its subsequent addition, CTAB can interact and form a complex with PSS because the electrostatic attraction between CTAB and PSS is much stronger than that between AO and PSS, which results in significant fluorescence recovery. Interestingly, the proposed method can be applied for the discrimination and detection of surfactants with different hydrocarbon chain lengths due to their different binding affinity toward PSS. The detection limit for CTAB is as low as 0.2 µg/mL and the linear range is from 0.5 to 3.5 µg/mL. Moreover, we applied the sensor to the successful detection of CTAB in water samples. Copyright © 2015 John Wiley & Sons, Ltd.

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Electronic Spectra and Electronic Structures of Some Antimicrobials Derived from Proflavine

Cited by 15 publications

References 4 publications

Synthesis and binding of proflavine diazides as functional intercalators for directed assembly on DNA

Synthesis and binding of proflavine diazides as functional intercalators for directed assembly on DNA

Adsorption complexes of acridine diaminoderivatives on silica surface

Sensitive and selective turn‐on fluorescence method for cetyltrimethylammonium bromide determination based on acridine orange–polystyrene sulfonate complex

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