Phosphorus–nitrogen compounds part 27. Syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing secondary amino and pendant (4-fluorobenzyl)spiro groups

Akbaş, Hüseyin; Okumuş, Aytuğ; Kılıç, Zeynel; Hökelek, Tuncer; Süzen, Yasemin; Koç, L. Yasemin; Açık, Leyla; Çelik, Zeliha

doi:10.1016/j.ejmech.2013.09.046

Cited by 78 publications

(36 citation statements)

References 23 publications

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“…The results indicate that compound 4d was monoprotonated with the nitrogen of phosphazene ring non-adjacent to the NO spiro ring. However, in the literature the protonation was observed from the nitrogen atom of phosphazene ring adjacent to the NN spiro ring [23]. The NMR results exhibit that all the compounds are likely to be protonated in the same fashion.…”

Section: Syntheses and Characterizations The Intermediate Schiff Basmentioning

confidence: 80%

“…In PILs 4d, the endocyclic PN bond lengths of the phosphazene ring were found to be in the range of 1.575(4)-1.666(4) Å (average value is 1.608(2) Å), compared with the corresponding values [1.588(1)-1.599(1) Å, average value is 1.595(1) Å] of the analogues phosphazene free bases [23]. In addition, the exocyclic PN bond lengths of 4d are in the range of 1.581(4)-1.649(4) Å (average value is 1.612(5) Å).…”

Section: Syntheses and Characterizations The Intermediate Schiff Basmentioning

confidence: 99%

“…The amine-based PILs were also reported by Bicak [21] and by Karadag [22]. Nevertheless, there is only one paper about the PILs based on cyclotriphosphazene with salicylic acid in the literature [23].…”

Section: Introductionmentioning

confidence: 96%

“…In addition, the exocyclic PN bond lengths of 4d are in the range of 1.581(4)-1.649(4) Å (average value is 1.612(5) Å). The corresponding values of analogues phosphazene free bases and its salts are in the ranges of 1.652(1)-1.674(1) Å (average value is 1.663(1) Å) and 1.625(2)-1.647(2) Å (average value is 1.639(2) Å) [23] (Table 2). In 4d, the P2N2 (1.655(4) Å) and P3N2 (1.666(4) Å) bond lengths are considerably larger than those of other PN bond lengths, depending on the protonation of N2 atom.…”

Section: Syntheses and Characterizations The Intermediate Schiff Basmentioning

confidence: 99%

“…It is found that aminocyclophosphazene derivatives have antimicrobial activity against bacteria and fungi [15][16][17]. The interactions between DNA and the phosphazene derivatives have also been investigated in the two last decades [18,19].…”

Section: Introductionmentioning

confidence: 99%

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The Syntheses and Structural Characterizations, Antimicrobial Activity and in Vitro Dna Binding of 4-Fluorobenzylspiro(n/O)cyclotriphosphazenes and Their Phosphazenium Salts

Elmas¹,

Okumuş²,

Kılıç³

et al. 2016

J. Turk. Chem. Soc., Sect. A: Chem.

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Abstract:In the present study, the condensation reaction of N3P3Cl6 (1) with sodium 3-(4-fluorobenzylamino)-1-propanoxide gave partly substituted 4-fluorobenzylspirocyclotriphosphazene (2). The Cl replacement reactions of 2 with excess benzylamine, n-hexylamine, n-butylamine and n-propylamine led to the formation of the corresponding 4-fluorobenzylspiro(N/O)tetrabenzylamino (3a), tetrahexylamino (3b), tetrabutylamino (3c) and tetrapropylamino (3d) cyclotriphosphazenes. With the protic ionic liquids (PILs), phosphazenium salts (4a-4d), were obtained from the reactions of the corresponding phosphazene bases (3a-3d) with gentisic acid in dry THF. The structures of all the isolated cyclotriphosphazene derivatives were determined by elemental analyses, FTIR and H} NMR techniques. The crystal structure of 4d was verified by X-ray diffraction analysis. All the compounds were screened for antibacterial and antifungal activities against bacteria and yeast strains. The interactions of the compounds with supercoiled pUC18 plasmid DNA were investigated.

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Section: Syntheses and Characterizations The Intermediate Schiff Basmentioning

confidence: 80%

Section: Syntheses and Characterizations The Intermediate Schiff Basmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

Section: Syntheses and Characterizations The Intermediate Schiff Basmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The Syntheses and Structural Characterizations, Antimicrobial Activity and in Vitro Dna Binding of 4-Fluorobenzylspiro(n/O)cyclotriphosphazenes and Their Phosphazenium Salts

Elmas¹,

Okumuş²,

Kılıç³

et al. 2016

J. Turk. Chem. Soc., Sect. A: Chem.

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The comparative reactions of 2‐cis‐4‐ansa and spiro cyclotetraphosphazenes with difunctional ligands: Structural and stereogenic properties, electrochemical, antimicrobial and cytotoxic activity studies

Okumuş

Elmas

Kılıç

et al. 2021

Applied Organom Chemis

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In this study, two kinds of compounds, namely, mono‐ferrocenyl‐2‐cis‐4‐dichloro‐ansa‐ (2,4‐ansa; 3) and mono‐ferrocenyl‐spiro‐ (spiro; 4) hexachlorocyclotetraphosphazenes, were obtained by the Cl replacement reaction of N4P4Cl8 (1) with an equimolar amount of sodium 3‐(N‐ferrocenylmethylamino)‐1‐propanoxide (2). The reactions of 2,4‐ansa (3) with excess diamines and dialkoxides resulted in the formation of ansa‐cyclotetraphosphazenes (3a–3e). Spiro (4) was reacted with excess diamines and dialkoxides to give the mono‐ferrocenyl‐spiro‐cyclotetraphosphazenes (4a–4d). Although 2,4‐ansa (3) produced the dispiro (3a) with N‐(4‐fluorobenzyl)‐N′‐methylethane‐1,2‐diamine, it afforded both monospiro (3b) and dispiro (3c) with N‐(4‐fluorobenzyl)‐N′‐methylpropane‐1,3‐diamine. However, spiro (4) yielded a trispiro (4a) with N‐(4‐fluorobenzyl)‐N′‐methylethane‐1,2‐diamine and 2,6‐dispiro (4b) with N‐(4‐fluorobenzyl)‐N′‐methylpropane‐1,3‐diamine. The structures of the phosphazenes were elucidated by FTIR, ESI‐MS and/or HRMS, spectroscopic and crystallographic (for 3f and 4b) data. Furthermore, the electrochemical findings of cyclotetraphosphazenes exhibited electrochemically reversible one‐electron oxidation of Fe‐redox centre. As an example, the chirality of 3c was investigated by 31P NMR spectroscopy on the addition of (R)‐(+)‐2,2,2‐trifluoro‐1‐(9′‐anthryl)‐ethanol, chiral solvating agent (CSA). The circular dichroism (CD) (for 3d and 3e), HPLC (for 3d, 3e and 3f) and X‐ray (for 3f) display that these compounds have chirality (RS′ or SR′) in the solution and solid state. This paper also focuses on the antimicrobial activities, the interactions with pBR322 DNA, in vitro anticancer activity against L929 fibroblast and MCF7 breast cells, and antituberculosis activity against Mycobacterium tuberculosis H37Rv of the cyclotetraphosphazenes.

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Phosphazene Tripeptide Conjugates: Design, Synthesis, In Vitro Cytotoxicity and Genotoxicity, Molecular Interactions in Binding Pockets on Human Breast and Colon Cancer Cell Lines

Çalışkan,

Yüksel,

Çapan

et al. 2024

ChemMedChem

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The biological activity of both cyclophosphazenes and peptides makes these compounds important for new studies in medicinal chemistry. For this purpose, five different phosphazene‐peptide conjugates synthesized from dichlorocyclotriphosphazene and tyrosine‐containing tripeptides. The synthesized compounds were evaluated for their in vitro cytotoxic activities against human breast (MCF‐7) and colon (Caco‐2) cancer cell lines using MTT assay. The derivatives induced cell death through DNA damage, with notable effects in Caco‐2 cell lines. Specifically, DTVV, DTVG, and DTVA were cytotoxic at 50 and 100 µM, while DTVP and DTVM were effective at 25, 50, and 100 µM. DTVM outperformed Tamoxifen at 50 µM in the MCF‐7 cell line. DNA damage studies of the compounds were performed using the comet assay method.The findings indicated that cell death occurred via a DNA damage mechanism. The molecular intricacies of DTVA, DTVG, DTVM, DTVP and DTVV within the VEGFR2 kinase domain and Cyclophilin_CeCYP16‐Like Domain binding pockets and various interactions, docking scores and potential activities of these derivatives were investigated. The differences in docking scores and interaction profiles highlight the potential efficacy and specificity of these compounds in targeting breast and colon cancer cells. These findings highlight the potential of phosphazene‐peptide derivatives as therapeutic agents in cancer treatment.

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Phosphorus–nitrogen compounds part 27. Syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing secondary amino and pendant (4-fluorobenzyl)spiro groups

Cited by 78 publications

References 23 publications

The Syntheses and Structural Characterizations, Antimicrobial Activity and in Vitro Dna Binding of 4-Fluorobenzylspiro(n/O)cyclotriphosphazenes and Their Phosphazenium Salts

The Syntheses and Structural Characterizations, Antimicrobial Activity and in Vitro Dna Binding of 4-Fluorobenzylspiro(n/O)cyclotriphosphazenes and Their Phosphazenium Salts

The comparative reactions of 2‐cis‐4‐ansa and spiro cyclotetraphosphazenes with difunctional ligands: Structural and stereogenic properties, electrochemical, antimicrobial and cytotoxic activity studies

Phosphazene Tripeptide Conjugates: Design, Synthesis, In Vitro Cytotoxicity and Genotoxicity, Molecular Interactions in Binding Pockets on Human Breast and Colon Cancer Cell Lines

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