Proflavine an acridine DNA intercalating agent and strong antimicrobial possessing potential properties of carcinogen

Gatasheh, Mansour K.; Kannan, Subburaj; Hemalatha, K.; Imrana, N.

doi:10.1016/j.kijoms.2017.07.003

Cited by 32 publications

(26 citation statements)

References 8 publications

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“…Акридинові барвники порушують реплікацію та транскрипцію ДНК мікроорганізмів [3]. Вони можуть впливати на ДНК людини і, вірогідно, спричиняти канцерогенну дію [52].…”

Section: ) барвники акридинового триарилметанового і фентіазинового рядів (рис 3)unclassified

Modern chemical disinfectants and antiseptics. Part I

Britsun¹,

Simurova²,

Popova³

et al. 2021

J. org. pharm. chem.

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Aim. To generalize and systematize information on the properties of modern chemical disinfectants and antiseptic agents (DA and AA).Results and discussion. The review provides generalized and systematized information on the properties of modern chemical DA and AA – alkylating reagents, aldehydes, amides, amidines, bisguanidines, dyes, halogenated reagents, halogens and their complexes, 2-nitrofuran derivatives. The classification of DA and AA by their chemical structure was carried out. The activity spectra, possible application ways and forms of DA and AA were given. Their toxicity and impact on the environment were described as well.Conclusions. On the basis of the analysis carried out it was shown that aldehydes, halogen-active compounds and halogen-containing complexes are modern effective DA and AA with a wide spectrum of biocidal action. Amides, amidines and bisguanidines are characterized by a narrow spectrum of activity. Dyes and 2-nitrofuran derivatives are old-fashioned antiseptics.

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Section: ) барвники акридинового триарилметанового і фентіазинового рядів (рис 3)unclassified

Modern chemical disinfectants and antiseptics. Part I

Britsun¹,

Simurova²,

Popova³

et al. 2021

J. org. pharm. chem.

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“…It has been widely used in photodynamic catalysis as an antimicrobial and in several other biomedical applications. [42] Besides, polyphenolic moieties doped in porous biomaterials, such as 2,4,6triformylphloroglucinol (TFP), are also used for diagnosis in medical applications owing to their photocatalytic potential. [43] Herein, for the first time, we report the synthesis of a novel COF, TPDA (chemical structure, see Figure 1), as a molecular photosensitizer for APCT bearing an acridine skeleton (DAA) and phloroglucinol-building blocks (TFP).…”

Section: Introductionmentioning

confidence: 99%

Acridine‐Based Covalent Organic Framework Photosensitizer with Broad‐Spectrum Light Absorption for Antibacterial Photocatalytic Therapy

Zhang

Guo

Zou

et al. 2021

Adv Healthcare Materials

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Antibiotic resistance is considered as one of the serious public health issues. Antibacterial photocatalytic therapy, a clinically proven antibacterial therapy, is gaining increasing attention in recent years owing to its high efficacy. Here, an acridine-based covalent organic framework (COF) photosensitizer, named TPDA, with multiple active sites is synthesized via Schiff base condensation between 2,4,6-triformylphloroglucinol (TFP) and 3,6-diaminoacridine (DAA). Owing to the increased conjugation effect of the COF skeleton and outstanding light harvesting ability of DAA, TPDA exhibits a narrow optical band gap (1.6 eV), enhancing light energy transformation and conferring a wide optical absorption spectrum (intensity arbitrary unit > 0.8) ranging from the UV to near-infrared region. Moreover, TPDA shows high antibacterial activities against both gram-negative and gram-positive bacteria within a short time (10 min) of light irradiation and is found to efficiently protect fish from skin infections. Molecular dynamics simulation data show that the introduction of DAA and TFP facilitates the interaction between TPDA and bacteria and is conducive to reactive oxygen species migration, which further improves the antimicrobial performance. These findings indicate the potential of TPDA as a novel photosensitive material for photodynamic therapy.

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“…Recently, the total synthesis of inubosine B 6 , an acridine alkaloid that initiates neuroregeneration, has been reported ( Figure 1 ) [ 10 ]. Antimicrobial properties are another important category of biological activity displayed by acridine derivatives [ 11 , 12 ]. Proflavine 7 is the example of a typical antibacterial and antifungal agent, while quinacrine 8 exhibits antimalarial properties ( Figure 1 ) [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Biologically Active Proflavine Ureas Designed on the Basis of Predicted Entropy Changes

et al. 2021

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A novel series of proflavine ureas, derivatives 11a–11i, were synthesized on the basis of molecular modeling design studies. The structure of the novel ureas was obtained from the pharmacological model, the parameters of which were determined from studies of the structure-activity relationship of previously prepared proflavine ureas bearing n-alkyl chains. The lipophilicity (LogP) and the changes in the standard entropy (ΔS°) of the urea models, the input parameters of the pharmacological model, were determined using quantum mechanics and cheminformatics. The anticancer activity of the synthesized derivatives was evaluated against NCI-60 human cancer cell lines. The urea derivatives azepyl 11b, phenyl 11c and phenylethyl 11f displayed the highest levels of anticancer activity, although the results were only a slight improvement over the hexyl urea, derivative 11j, which was reported in a previous publication. Several of the novel urea derivatives displayed GI50 values against the HCT-116 cancer cell line, which suggest the cytostatic effect of the compounds azepyl 11b–0.44 μM, phenyl 11c–0.23 μM, phenylethyl 11f–0.35 μM and hexyl 11j–0.36 μM. In contrast, the novel urea derivatives 11b, 11c and 11f exhibited levels of cytotoxicity three orders of magnitude lower than that of hexyl urea 11j or amsacrine.

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Proflavine an acridine DNA intercalating agent and strong antimicrobial possessing potential properties of carcinogen

Cited by 32 publications

References 8 publications

Modern chemical disinfectants and antiseptics. Part I

Modern chemical disinfectants and antiseptics. Part I

Acridine‐Based Covalent Organic Framework Photosensitizer with Broad‐Spectrum Light Absorption for Antibacterial Photocatalytic Therapy

Synthesis of Novel Biologically Active Proflavine Ureas Designed on the Basis of Predicted Entropy Changes

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