Research Article

Synthesis and antimicrobial effects of cyclotriphosphazenes containing monocarbonyl curcumin analogs

Volume: 22 Number: 4 June 27, 2025

Synthesis and antimicrobial effects of cyclotriphosphazenes containing monocarbonyl curcumin analogs

Abstract

Six novel bridged structure cyclotriphosphazenes (4a-f) were synthesized from the reactions of aryloxycyclotriphosphazenes [aryloxy= phenoxy (2a) and (2-naphthoxy) (2b)] with monocarbonyl curcumin derivatives [acetone (3a), cyclopentanone (3b) and cyclohexanone (3c)] for the first time. The structures of the compounds (4a-f) were defined by elemental analysis, FT-IR, mass and NMR (1H and 31P) spectroscopies. The antimicrobial properties of the compounds (2a, 2b, 3a-c and 4a-f) were screened in vitro against Escherichia coli ATCC 8739, Staphylococcus aureus ATCC 29213, Bacillus subtilis ATCC 6633, Bacillus cereus DSMZ 4312 and Candida albicans ATCC 10231. In addition, effective substance of 3b and 4c were evaluated Minimal Inhibition Concentration.

Keywords

References

  1. [1] Liang G, Yang S, Jiang L, Zhao Y, Shao L, Xiao J, Ye F, Li Y, Li X. Synthesis and antibacterial properties of monocarbonyl analogues of curcumin. Chem Pharm Bull. 2008; 56(2): 162-167. [CrossRef]
  2. [2] Cao J, Liu Y, Jia L, Zhou H-M, Kong Y, Yang G, Jiang L-P, Li Q-J, Zhong L-F. Curcumin induces apoptosis through mitochondrial hyperpolarization and mtDNA damage in human hepatoma G2 cells. Free Radical Bio Med. 2007; 43(6): 968-975. [CrossRef]
  3. [3] Altunatmaz SS, Aksu FY, Issa G, Kahraman BB, Altiner DD, Buyukunal SK. Antimicrobial effects of curcumin against L. monocytogenes, S. aureus, S. Typhimurium and E. coli O157:H7 pathogens in minced meat. Vet Med-Czech. 2016; 61(5): 256-262.
  4. [4] Maheshwari RK, Singh AK, Gaddipati J, Srimal RC. Multiple biological activities of curcumin: A short review. Life Sci. 2006; 78(18): 2081-2087. [CrossRef]
  5. [5] Sharma RA, Steward WP, Gescher AJ. Pharmacokinetics and pharmacodynamics of curcumin. Adv Exp Med Biol. 2007; 595: 453-470. [CrossRef]
  6. [6] Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB. Bioavailability of Curcumin: problems and promises. Mol Pharmacol. 2007; 4(6): 807-818.
  7. [7] Sanabria-Ríos DJ, Rivera-Torres Y, Rosario J, Gutierrez R, Torres-García Y, Montano N, Ortíz-Soto G, Ríos-Olivares E, Rodríguez JW, Carballeira NM. Chemical conjugation of 2-hexadecynoic acid to C5-curcumin enhances its antibacterial activity against multi-drug resistant bacteria. Bioorg Med Chem Lett. 2015; 25(22): 5067-5071. [CrossRef]
  8. [8] Zambre AP, Kulkarni VM, Padhye S, Sandur SK, Aggarwal BB. Novel curcumin analogs targeting TNF-induced NF-κB activation and proliferation in human leukemic KBM-5 cells. Bioorg Med Chem. 2006; 14(21): 7196-7204. [CrossRef]

Details

Primary Language

English

Subjects

Pharmaceutical Chemistry

Journal Section

Research Article

Authors

Mine Gül Şeker * This is me
0009-0007-4176-6191
Türkiye

Tuğçe Akbal This is me
Türkiye

Neslihan Avşar This is me
0000-0002-7315-5674
Türkiye

Publication Date

June 27, 2025

Submission Date

January 8, 2018

Acceptance Date

February 18, 2018

Published in Issue

Year 2018 Volume: 22 Number: 4

APA
Gül Şeker, M., Akbal, T., Atilla, D., Avşar, N., & İbişoğlu, H. (2025). Synthesis and antimicrobial effects of cyclotriphosphazenes containing monocarbonyl curcumin analogs. Journal of Research in Pharmacy, 22(4), 536-546. https://izlik.org/JA45LT33ER
AMA
1.Gül Şeker M, Akbal T, Atilla D, Avşar N, İbişoğlu H. Synthesis and antimicrobial effects of cyclotriphosphazenes containing monocarbonyl curcumin analogs. J. Res. Pharm. 2025;22(4):536-546. https://izlik.org/JA45LT33ER
Chicago
Gül Şeker, Mine, Tuğçe Akbal, Devrim Atilla, Neslihan Avşar, and Hanife İbişoğlu. 2025. “Synthesis and Antimicrobial Effects of Cyclotriphosphazenes Containing Monocarbonyl Curcumin Analogs”. Journal of Research in Pharmacy 22 (4): 536-46. https://izlik.org/JA45LT33ER.
EndNote
Gül Şeker M, Akbal T, Atilla D, Avşar N, İbişoğlu H (June 1, 2025) Synthesis and antimicrobial effects of cyclotriphosphazenes containing monocarbonyl curcumin analogs. Journal of Research in Pharmacy 22 4 536–546.
IEEE
[1]M. Gül Şeker, T. Akbal, D. Atilla, N. Avşar, and H. İbişoğlu, “Synthesis and antimicrobial effects of cyclotriphosphazenes containing monocarbonyl curcumin analogs”, J. Res. Pharm., vol. 22, no. 4, pp. 536–546, June 2025, [Online]. Available: https://izlik.org/JA45LT33ER
ISNAD
Gül Şeker, Mine - Akbal, Tuğçe - Atilla, Devrim - Avşar, Neslihan - İbişoğlu, Hanife. “Synthesis and Antimicrobial Effects of Cyclotriphosphazenes Containing Monocarbonyl Curcumin Analogs”. Journal of Research in Pharmacy 22/4 (June 1, 2025): 536-546. https://izlik.org/JA45LT33ER.
JAMA
1.Gül Şeker M, Akbal T, Atilla D, Avşar N, İbişoğlu H. Synthesis and antimicrobial effects of cyclotriphosphazenes containing monocarbonyl curcumin analogs. J. Res. Pharm. 2025;22:536–546.
MLA
Gül Şeker, Mine, et al. “Synthesis and Antimicrobial Effects of Cyclotriphosphazenes Containing Monocarbonyl Curcumin Analogs”. Journal of Research in Pharmacy, vol. 22, no. 4, June 2025, pp. 536-4, https://izlik.org/JA45LT33ER.
Vancouver
1.Mine Gül Şeker, Tuğçe Akbal, Devrim Atilla, Neslihan Avşar, Hanife İbişoğlu. Synthesis and antimicrobial effects of cyclotriphosphazenes containing monocarbonyl curcumin analogs. J. Res. Pharm. [Internet]. 2025 Jun. 1;22(4):536-4. Available from: https://izlik.org/JA45LT33ER