Journals / Turkish Journal of Chemistry / 2020 / Cilt: 44 - Sayı: 1

Synthesis and spectroscopic properties of (N/O) mono- and dispirocyclotriphosphazene derivatives with benzyl pendant arms: study of biological activity

Pages
15–30
Publication Date
2022-11-05
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

The phosphazeneDNA interaction studies of the cyclotriphosphazenes revealed that phosphazenes 3, 4, and 15 had a substantial effecton supercoiled DNA by cleavage of the double helix.

📌 3 Key Takeaways

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Objective & Hypothesis:: The Cl replacement reactions of hexachlorocyclotriphosphazene (trimer; N3P3 Cl 6) with sodium (N-benzyl)-aminopropanoxides (1 and 2) produced monospiro- (3 and 4), cis-, and trans-dispirocyclotriphosphazenes (13–16).
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Key Findings & Data:Themonospiro tetrakis-aminocyclotriphosphazenes (5–12) were obtained by the Cl substitutions of 3 and 4 with differentsecondary amines.
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Conclusion & Impact:The phosphazeneDNA interaction studies of the cyclotriphosphazenes revealed that phosphazenes 3, 4, and 15 had a substantial effecton supercoiled DNA by cleavage of the double helix.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

: The Cl replacement reactions of hexachlorocyclotriphosphazene (trimer; N3P3 Cl 6) with sodium (N-benzyl)-aminopropanoxides (1 and 2) produced monospiro- (3 and 4), cis-, and trans-dispirocyclotriphosphazenes (13–16). Themonospiro tetrakis-aminocyclotriphosphazenes (5–12) were obtained by the Cl substitutions of 3 and 4 with differentsecondary amines. The cis- (13 and 14) and trans-dispirophosphazenes (15 and 16) possessed 2 chiral P centers, andthey were able to present meso and racemic forms, respectively. Moreover, the structures of compounds 5 and 14were designated using X-ray data. The absolute configuration of compound 14 was found as SR in the solid state.Analytical and spectroscopic data of the phosphazenes were consistent with their suggested structures. Antimicrobialactivities of the benzyl-pendant-armed cyclotriphosphazenes were scrutinized against G(+) and G(−) bacteria andyeast strains. The bacterium most affected by the synthesized compounds was Pseudomonas aeruginosa. Minimuminhibitory concentrations and minimal bacterial concentrations were in the range of 125–500 µM. Interactions betweenthe phosphazenes (3–12 and 15) and plasmid DNA were studied with agarose gel electrophoresis. The phosphazeneDNA interaction studies of the cyclotriphosphazenes revealed that phosphazenes 3, 4, and 15 had a substantial effecton supercoiled DNA by cleavage of the double helix.

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Cite This Article

İŞCAN, Ö., CEMALOĞLU, R., ASMAFİLİZ, N., KILIÇ, Z., HÖKELEK, T., AÇIK, L., ÖZBEDEN, P. (2022). Synthesis and spectroscopic properties of (N/O) mono- and dispirocyclotriphosphazene derivatives with benzyl pendant arms: study of biological activity. Turkish Journal of Chemistry, Cilt: 44 - Sayı: 1, 15–30. https://ajindex.com/articles/601602

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References (16)

  1. Allen CW. Linear, cyclic and polymeric phosphazenes. Coordination Chemistry Reviews 1994; 130: 137-173
  2. Chandrasekhar V, Chakraborty A. Organophosphorus Chemistry. London, UK: Royal Society of Chemistry, 2019
  3. Allen CW. Regio- and stereochemical control in substitution reactions of cyclophosphazenes. Chemical Reviews 1991; 91: 119-135
  4. Stewart FF. Organophosphorus Chemistry. London, UK: Royal Society of Chemistry, pp. 397-430
  5. Asmafiliz N, İlter EE, Kılıç Z, Hökelek T, Şahin E. Phosphorus-nitrogen compounds: Part 15. Synthesis, anisochronism and the relationship between crystallographic and spectral data of monotopic spiro-crypta phosphazenes. Journal of Chemical Sciences 2008; 120: 363-376
  6. Jaeger R, Gleria M. Poly(organophosphazene)s and related compounds: Synthesis, properties and applications. Progress in Polymer Science 1998; 23: 179-276
  7. Gleria M, Jaeger R. de. Phosphazenes: A Worldwide Insight. New York, NY, USA: Nova Publishersý, 2004
  8. Asmafiliz N, Kılıç Z, Öztürk A, Hökelek T, Koç LY et al. Phosphorus-nitrogen compounds
  9. Syntheses, stereogenic properties, structural and electrochemical investigations, biological activities, and DNA interactions of new spirocyclic mono- and bisferrocenylphosphazene derivatives. Inorganic Chemistry 2009; 48: 10102-10116
  10. Uslu A, Yeşilot S. Chiral configurations in cyclophosphazene chemistry. Coordination Chemistry Reviews 2015; 291: 28-67
  11. Kumar NS, Kumara Swamy KC. Synthesis and structures of unsymmetrical bis- and tris-cyclotriphosphazenes. Polyhedron 2004; 23: 979-985
  12. İlter EE, Asmafiliz N, Işıklan M, Kılıç Z, Çaylak N et al. Phosphorus-nitrogen compounds
  13. Synthesis, stereogenism, and structural investigations of novel N/O spirocyclic phosphazene derivatives. Inorganic Chemistry 2007; 46 (23): 9931-9944
  14. Tümer Y, Asmafiliz N, Zeyrek CT, Kılıç Z, Açık L et al. Syntheses, spectroscopic and crystallographic characterizations of cis- and trans-dispirocyclic ferrocenylphosphazenes: molecular dockings, cytotoxic and antimicrobial activities. New Journal of Chemistry 2018; 42 (3): 1740-1756
  15. Tümer Y, Asmafiliz N, Kılıç Z, Aydın B, Açık L et al. Phosphorus-nitrogen compounds: Part 43. Syntheses, spectroscopic characterizations and antimicrobial activities of cis- and trans-N/O dispirocyclotriphosphazenes containing ferrocenyl pendant arms. Journal of Molecular Structure 2018; 1173: 885-893
  16. Beşli S, Allen CW, Mutlu Balcı C, Kara G, Yeşilot S et al. Stereochemical as