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Proflavine

(Synonyms: 3,6-Diaminoacridine) 目录号 : GC25784

Proflavine (3,6-Diaminoacridine) is a disinfectant bacteriostatic against many gram-positive bacteria. It is a topical antiseptic used mainly in wound dressings.

Proflavine Chemical Structure

Cas No.:92-62-6

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产品描述

Proflavine (3,6-Diaminoacridine) is a disinfectant bacteriostatic against many gram-positive bacteria. It is a topical antiseptic used mainly in wound dressings.

Chemical Properties

Cas No. 92-62-6 SDF Download SDF
别名 3,6-Diaminoacridine
分子式 C13H11N3 分子量 209.25
溶解度 DMSO: 23 mg/mL (109.92 mM);Water: Insoluble;Ethanol: 2 mg/mL (9.56 mM) 储存条件 Store at -20°C
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1 mM 4.779 mL 23.8949 mL 47.7897 mL
5 mM 0.9558 mL 4.779 mL 9.5579 mL
10 mM 0.4779 mL 2.3895 mL 4.779 mL
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Research Update

Proflavine/acriflavine derivatives with versatile biological activities

J Appl Toxicol 2020 Jan;40(1):64-71.PMID:31222780DOI:10.1002/jat.3818.

Proflavine derivatives are extremely interesting chemotherapeutic agents, which have shown promising pharmaceutical potential due to their wide range of biological activities. This review summarizes the current state of research into the anticancer, antimicrobial, antimalarial and antileishmanial properties of these attractive compounds. Our attention has focused on new classes of Proflavine conjugates, which display significant levels of anticancer activity. Highly promising cytotoxic properties have been identified in Proflavine conjugates with imidazolidinones, ureas and thioureas. In particular, proflavine-dialkyldithioureas displayed substantial cytotoxic effect against the human leukemia HL-60 cells with IC50 values from 7.2 to 34.0 μm. As well, palladium complexes with Proflavine ligand have important biologic activity. The LC50 values of these complexes were significantly lower than that of cisplatin against the SK-BR-3 cell line.

Excited-State Dynamics of Proflavine after Intercalation into DNA Duplex

Molecules 2022 Nov 23;27(23):8157.PMID:36500248DOI:10.3390/molecules27238157.

Proflavine is an acridine derivative which was discovered as one of the earliest antibacterial agents, and it has been proven to have potential application to fields such as chemotherapy, photobiology and solar-energy conversion. In particular, it is well known that Proflavine can bind to DNA with different modes, and this may open addition photochemical-reaction channels in DNA. Herein, the excited-state dynamics of Proflavine after intercalation into DNA duplex is studied using femtosecond time-resolved spectroscopy, and compared with that in solution. It is demonstrated that both fluorescence and the triplet excited-state generation of Proflavine were quenched after intercalation into DNA, due to ultrafast non-radiative channels. A static-quenching mechanism was identified for the proflavine-DNA complex, in line with the spectroscopy data, and the excited-state deactivation mechanism was proposed.

Proflavine Hemisulfate as a Fluorescent Contrast Agent for Point-of-Care Cytology

PLoS One 2015 May 11;10(5):e0125598.PMID:25962131DOI:10.1371/journal.pone.0125598.

Proflavine hemisulfate, an acridine-derived fluorescent dye, can be used as a rapid stain for cytologic examination of biological specimens. Proflavine fluorescently stains cell nuclei and cytoplasmic structures, owing to its small amphipathic structure and ability to intercalate DNA. In this manuscript, we demonstrated the use of Proflavine as a rapid cytologic dye on a number of specimens, including normal exfoliated oral squamous cells, cultured human oral squamous carcinoma cells, and leukocytes derived from whole blood specimens using a custom-built, portable, LED-illuminated fluorescence microscope. No incubation time was needed after suspending cells in 0.01% (w/v) Proflavine diluted in saline. Images of Proflavine stained oral cells had clearly visible nuclei as well as granular cytoplasm, while stained leukocytes exhibited bright nuclei, and highlighted the multilobar nature of nuclei in neutrophils. We also demonstrated the utility of quantitative analysis of digital images of Proflavine stained cells, which can be used to detect significant morphological differences between different cell types. Proflavine stained oral cells have well-defined nuclei and cell membranes which allowed for quantitative analysis of nuclear to cytoplasmic ratios, as well as image texture analysis to extract quantitative image features.

Structure and dynamics of Proflavine association around DNA

Phys Chem Chem Phys 2016 Apr 21;18(15):10383-91.PMID:27030311DOI:10.1039/c5cp07789c.

Proflavine is a small molecule that intercalates into DNA and, thereby, acts as an anticancer agent. Intercalation of Proflavine is shown to be a two-step process in which the first step is believed to be the formation of a pre-intercalative outside bound state. Experimental studies so far have been unable to capture the nature of the outside bound state. However, the sub-millisecond timescale observed in fluorescence kinetic experiments is often attributed to the binding of Proflavine outside of DNA. Here, we have performed molecular dynamics simulations with multiple Proflavine molecules to study the structure and dynamics of the formation of the outside bound state of DNA at different ion concentrations. We observed that the timescale of the outside bound state formation is, at least, five orders of magnitude faster (in nanoseconds) than the experimentally reported timescale (sub-milliseconds) attributed to binding outside DNA. Moreover, we also observed the stacked arrangement of Proflavine all around DNA, which is different from the experimentally predicted stacking arrangement perpendicular to the helical axis of DNA in the close vicinity of the phosphate groups. This study, therefore, provides insight into the molecular structure and dynamics of the pre-intercalative outside bound state and will help in understanding the overall intercalation mechanism.

Proflavine INHIBITION OF VACCINIA VIRUS SYNTHESIS

J Bacteriol 1965 Apr;89(4):977-83.PMID:14276124DOI:10.1128/jb.89.4.977-983.1965.

Bubel, H. Curt (University of Cincinnati College of Medicine, Cincinnati, Ohio), and David A. Wolff. Proflavine inhibition of vaccinia virus synthesis. J. Bacteriol. 89:977-983. 1965.-The synthesis of vaccinia virus, hemagglutinin, and blocking antigen, as well as the development of cytopathic effects, were inhibited by low concentrations of Proflavine. This inhibitor did not exert a selective effect on any particular portion of the virus synthetic cycle. Proflavine added to infected KB cells during the eclipse period or later stages of virus maturation rapidly arrested further production of infectious virus and virus-related products. Suppression of virus synthesis was completely reversible, indicating that permanent damage to the virus synthetic mechanism did not result from a transient exposure to Proflavine. Photosensitization of maturating vaccinia virus by subinhibiting concentrations of Proflavine suggested an interaction of the inhibitor with viral nucleic acid.