Bis-phosphonium salts of pyridoxine: The relationship between structure and antibacterial activity

Pugachev, Mikhail V.; Shtyrlin, Nikita V.; Sapozhnikov, Sergey V.; Sysoeva, L. P.; Iksanova, Alfiya G.; Никитина, Е. В.; Мусин, Р. З.; Лодочникова, О. А.; Бердников, Е. А.; Shtyrlin, Yu. G.

doi:10.1016/j.bmc.2013.09.056

Cited by 39 publications

(28 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In particular, pyridoxine molecules carrying a 5-ethenyl substituent possess anti-inflammatory properties [1], 6-phenylethenyl substituted pyridoxines have been described as purine receptor antagonists [2], and 2-ethenyl derivatives possess antitumor activity [3]. In our group, we have systematically studied the chemistry and biological activity of pyridoxine derivatives (e.g., [4][5][6][7][8]). Recently, we described a number of cis-and trans-5-alkenyl substituted pyridoxines which demonstrated promising antitumor activity [7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antitumor Activity of Novel Pyridoxine-Based Bioisosteric Analogs of trans-Stilbenes

Pugachev

Nguyen

Bulatov

et al. 2017

Journal of Chemistry

Self Cite

View full text Add to dashboard Cite

A series of trans-6-phenylethenyl substituted pyridoxine derivatives, novel bioisosteric analogs of drugs based on trans-stilbene scaffold, were synthesized using the Wittig reaction of a bis-triphenylphosphonium pyridoxine derivative with various aromatic aldehydes. Two compounds demonstrated high activity against the estrogen-dependent MCF-7 (breast cancer) cell line with IC 50 in the range of 1.9-7.9 M and very good selectivity for other studied normal and tumor cells, including the estrogen receptor negative MDA-MB-231 breast cancer cells. The active compounds possessed an intense blue fluorescence, and this feature allowed us to effectively visualize them in cytoplasm and in nucleus. The obtained results make the described chemotype a promising starting point for the development of new anticancer agents for the therapy of estrogen-dependent malignancies.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis and Antitumor Activity of Novel Pyridoxine-Based Bioisosteric Analogs of trans-Stilbenes

Pugachev

Nguyen

Bulatov

et al. 2017

Journal of Chemistry

Self Cite

View full text Add to dashboard Cite

show abstract

“…Recently, we described a wide series of phosphonium and ammonium derivatives of pyridoxine [22,23,50,51]. Some of the described compounds possessed potent antibacterial activity with minimum inhibitory concentrations (MICs) in the range of 0.5-64 g/mL.…”

Section: Antibacterial Activitymentioning

confidence: 99%

“…Compounds 4a,b were purified using flash chromatography on C18 silica gel. Synthesis and analytical parameters of compounds 2a,b and 3a have been described previously [23], while compounds 3b and 4a,b are described in this work for the first time.…”

Section: Synthesismentioning

confidence: 99%

“…The key intermediates 2a,b have been obtained from initial pyridoxine hydrochloride 1 according to procedure described previously [23]. Reaction of 2a,b with triphenylphosphine and N-bromosuccinimide in dichloromethane gave the corresponding bromides 3a,b as the main products.…”

Section: Synthesismentioning

confidence: 99%

“…Synthesis and analytical parameters of compounds 2a,b and 3a have been described in our previous paper [23]. Fluconazole has been purchased from Sigma-Aldrich (USA)-SKU-Pack Size PHR1160-1G.…”

Section: Synthetic Proceduresmentioning

confidence: 99%

See 2 more Smart Citations

Fluconazole-Pyridoxine Bis-Triazolium Compounds with Potent Activity against Pathogenic Bacteria and Fungi Including Their Biofilm-Embedded Forms

Garipov

Pavelyev

Lisovskaya

et al. 2017

Journal of Chemistry

Self Cite

View full text Add to dashboard Cite

Two novel quaternary ammonium salts, bis-triazolium derivatives of fluconazole and pyridoxine, were synthesized by reaction of fluconazole with pyridoxine-based synthetic intermediates. The leading compound demonstrated pronounced antimycotic and antibacterial in vitro activity, comparable to or exceeding that of the reference antifungal (fluconazole, terbinafine) and antibacterial/antiseptic (miramistin, benzalkonium chloride) agents. In contrast to many antimicrobials, the leading compound was also active against biofilm-embedded staphylococci and Escherichia coli. While no biofilm structure destruction occurred, all compounds were able to diffuse into the matrix and reduce the number of colony-forming units by three orders of magnitude at 16 × MBC. The leading compound was significantly less toxic than miramistin and benzalkonium chloride and more toxic than the reference antifungal drugs. The obtained results make the described chemotype a promising starting point for the development of new broad-spectrum antimicrobial therapies with powerful effect on fungal and bacterial pathogens including their biofilmembedded forms.

show abstract

A Graftable Quaternary Ammonium Biocidal Polymer Reduces Biofilm Formation and Ensures Biocompatibility of Medical Devices

Bouloussa

Saleh‐Mghir

Valotteau

et al. 2021

Adv Materials Inter

View full text Add to dashboard Cite

demands from the elder population account for the rise of both invasive and non-invasive procedures comprising biomaterial implantation. [2] Substantial progress was made in terms of mechanical properties, biocompatibility, and biointegration resulting in excellent functional outcomes in multiple surgical specialties. On the other hand, there is to this date no consensus for an anti-infectious strategy in order to prevent biofilm formation on implanted surfaces. The consequences of nosocomial infections arising from surgical implants still represent a heavy burden on both patients and healthcare systems worldwide. [3] In spite of the advancements of antisepsis procedures, a significant and fixed proportion of nosocomial infections are still reported (from 1 to 2% for hip and knee joint replacement, respectively). Biofilm is an exopolysaccharidic matrix comprising bacteria with reduced antibiotic sensitivity and poor mechanical accessibility. [4-6] Biofilm formation plays a major role in the failure of conservative treatments (antibiotic use, wound debridement, and lavage) for implant-related infections. [7,8] A common rule is to perform implant removal to treat biofilm-related infections if a proper conservative treatment has previously failed, which explains the high morbidity caused by the management of A quaternized polyvinylpyridine (Q-PVP) polymer methanolic solution synthesized in a single step is used to covalently graft titanium surfaces. Q-PVP is quaternized with varying N + /N ratios. 1 cm 2 pure titanium plates are polished and activated. Treated samples are grafted by spin coating or dip-coating (grafting-to method). Surfaces are characterized by X-ray photoelectron spectroscopy, polarization modulation reflection absorption IR spectroscopy, atomic force microscopy, scanning electron microscopy, and surface charge density calculation. Polymer leaching is assessed at 7 days. Biocompatibility is assessed on MC3T3 and L929 cells (MTT-assay) and SEM. In vitro antibacterial activity is assessed on methicillin-resistant Staphylococcus aureus (MRSA) at 1 and 24 h (37 °C in brain heart infusion) and at 7 days in a biofilm model. Polymers exceeding 31.3 ± 0.7% quaternization led to bactericidal surfaces. Bactericidal activity increased with surface cationic density. Surface cationic density and biocompatibility are inversely correlated. Polymers with 44.6 ± 1.2% quaternization are antibacterial and biocompatible. High-density Q-PVP inhibited MRSA biofilm formation. Q-PVP is a promising candidate for antibacterial surface modification. Further in vivo studies are required.

show abstract

Bis-phosphonium salts of pyridoxine: The relationship between structure and antibacterial activity

Cited by 39 publications

References 19 publications

Synthesis and Antitumor Activity of Novel Pyridoxine-Based Bioisosteric Analogs of trans-Stilbenes

Synthesis and Antitumor Activity of Novel Pyridoxine-Based Bioisosteric Analogs of trans-Stilbenes

Fluconazole-Pyridoxine Bis-Triazolium Compounds with Potent Activity against Pathogenic Bacteria and Fungi Including Their Biofilm-Embedded Forms

A Graftable Quaternary Ammonium Biocidal Polymer Reduces Biofilm Formation and Ensures Biocompatibility of Medical Devices

Contact Info

Product

Resources

About