Synthesis of novel meso-ester oligopyrroles and evaluation of their antibacterial activities

Seda Çınar; Dilek Işık Taşgın; Nalan Oya San Keskin

doi:10.15671/hjbc.1731070

Synthesis of novel meso-ester oligopyrroles and evaluation of their antibacterial activities

Abstract

Phosphodiester or carboester functionalized dipyrromethane or tripyrrane derivatives at their meso-positions were synthesized by the addition reaction of pyrrole to corresponding active methylene compounds in the presence of trifluoroacetic acid catalyst. Structures of the synthesized compounds were characterized by NMR techniques. All compounds were tested for their antibacterial efficiencies against Gram-positive Staphylococcus aureus (S. aureus) and Gram-negative Escherichia coli (E. coli) bacteria. The results have shown the successful synthesis and good antibacterial activity to S. aureus and E. coli of dipyrromethane and tripyrrane derivatives.

Keywords

Supporting Institution

Ankara Hacı Bayram Veli University Coordinatorship of Scientific Research Projects

Project Number

07/2021-02

Thanks

This work was supported by Ankara Hacı Bayram Veli University Coordinatorship of Scientific Research Projects, (AHBV – BAP)

References

S. Sysak, B. Wicher, M. Kucinska, P. Kobylka, D. T. Mlynarczyk, R. Lesyk, E. Tykarska, M. Murias, T. Goslinski, W. Szczolko, Synthesis, physicochemical characterization and biological activity of novel pyrrole flavones, Sci. Rep., 15 (2025) 7385–7400.
B. S. Manya, M. R. P. Kumar, K. Rajagopal, A. Hassan, S. O. Rab, M. A. Alshehri, T. Bin Emran, Insights into the biological activities and substituent effects of Pyrrole Derivatives: The chemistry-biology connection, Chem. Biodiversity, 21 (2024) e202400534.
C. Comuzzi, A. Fiorot, A. Baggio, M. Maifreni, P. Strazzolini, M. Marino, S. Susmel, Imprinting pentaphyrin on conductive electropolymerized dipyrromethane films: A new strategy towards the synthesis of photokilling materials, ChemPlusChem, 85 (2020) 776-782.
Y. Verbandt, H. Thienpont, I. Veretennicoff, P. Geerlings, Optical properties of pyrrole oligomers: a coupled quantum oscillator approach, Chem. Phys. Letters, 251 (1996) 47-51.
M. Walesa-Chorab, R. Banasz, M. Kubicki, V. Patroniak, Dipyrromethane functionalized monomers as precursors of electrochromic polymers, Electrochim. Acta, 258 (2017) 571-581.
H. Falk, The chemistry of linear oligopyrroles and bile pigments, Springer-Verlag Wien New York, 1989.
B. Hong, V. V. Prabhu, S. Zhang, A. P. J. van den Heuvel, D. T. Dicker, L. Kopelovick, W. S. El-Deiry, Prodigiosin rescues deficient p53 signaling and antitumor effects via upregulating p73 and disrupting its interaction with mutant p53, Cancer Res., 74 (2014) 1153–1165.
D. Dalili, S. Fouladdel, N. Rastkari, N. Samadi, R. Ahmadkhaniha, A. Ardavan, E. Azizi, Prodigiosin, the red pigment of Serratia marcescens, shows cytotoxic effects and apoptosis induction in HT-29 and T47D cancer cell lines, Nat. Prod. Res., 26 (2012) 2078-2083.

S. Rastogi, E. Marchal, I. Uddin, B. Groves, J. Colpitts, S. A. McFarland, J. T. Davis, A. Thompson, Synthetic prodigiosenes and the influence of C-ring substitution on DNA cleavage, transmembrane chloride transport and basicity, Org. Biomol. Chem., 11 (2013) 3834-3845.
A. J. Castro, Antimalarial activity of prodigiosin, Nature, 213 (1967) 903-904.
K. Papireddy, M. Smilkstein, J. X. Kelly, S. M. Shweta Salem, M. Alhamadsheh, S. W. Haynes, G. L. Challis, K. A. Reynolds, Antimalarial activity of natural and synthetic prodiginines, J. Med. Chem., 54 (2011) 5296-5306.
C. Campàs, M. Dalmau, B. Montaner, M. Barragan, B. Bellosillo, D. Colomer, G. Pons, R. Perez-Tomas, J. Gil, Prodigiosin induces apoptosis of B and T cells from B-cell chronic lymphocytic leukemia, Leukemia, 17 (2003) 746–750.
M. Nguyen, R. C. Marcellus, A. Roulston, M. Watson, L. Serfass, S. R. Murthy Madiraju, D. Goulet, J. Viallet, L. Belec, X. Billot, S. Acoca, E. Purisima, A. Wiegmans, L. Cluse, R. W. Johnstone, P. Beauparlant, G. C. Shore, Small molecule obatoclax (GX15-070) antagonizes MCL-1 and overcomes MCL-1-mediated resistance to apoptosis, Proc. Natl. Acad. Sci. U.S.A., 104 (2007) 19512–19517.
T. Ishizuka, N. Grover, C. J. Kingsbury, H. Kotani, M. O. Senge, T. Kojima, Nonplanar porphyrins: synthesis, properties, and unique functionalities, Chem. Soc. Rev., 51 (2022) 7560-7630.
P. Kaur, S. Kaur, K. Singh, A fluoride selective dipyrromethane-TCNQ colorimetric sensor based on charge-transfer, Talanta, 84 (2011) 947-951.
A. Gautam, P. Rawat, R. N. Singh, N. R. Flores Holguin, Synthesis, spectroscopic and evaluation of anticancer activity of new hydrazone-containing dipyrromethane using experimental and theoretical approaches, J. Mol. Struct., 1260 (2022) 132781–132791.
M. Holiyachi, S. L. Shastri, B. M. Chougala, N. S. Naik, V. Pawar, L. A. Shastri, S. D. Joshi, V. A. Sunagar, Design and synthesis of new series of dipyrromethane-coumarin and porphyrin-coumarin derivatives: Excellent anticancer agents, J. Mol. Struct., 1237 (2021) 130424–130440.
R. Jorda, S. M. M. Lopes, E. Reznickova, V. Krystof, T. M. V. D. Pinho e Melo, Biological evaluation of dipyrromethanes in cancer cell lines: Antiproliferative and pro-apoptotic properties, ChemMedChem, 12 (2017) 701–711.
J. Jaratjaroonphong, S. Tuengpanya, R. Saeeng, S. Udompong, K. Srisook, Green synthesis and anti-inflammatory studies of a series of 1,1-bis(heteroaryl)alkane derivatives, Eur. J. Med. Chem., 83 (2014) 561–568.
I. Hwang, S. -H. Huang, S. Smith, V. Lynch, R. Custelcean, B. A. Moyer, N. Kumar, V. S. Bryantsev, J. L. Sessler, Direct extraction of sodium hydroxide by calix[4]pyrrole-based ion-pair receptors, J. Am. Chem. Soc., 145 (2023) 14387–14394.
D. Plazuk, J. Zakrzewski, Friedel-Crafts reaction of dimethyl 2-oxopropylphosphonate and diethyl 2,2-diethoxyethylphosphonate with electron-rich arenes, Phosphorus, Sulfur, Silicon Relat. Elem., 180 (2005) 2709–2715.
W. Vollmer, D. Blanot, M. A. De Pedro, Peptidoglycan structure and architecture, FEMS Microbiol Rev., 32 (2008) 149-167.
E. Marchal, I. Uddin, D. A. Smithen, C. L. A. Hawco, M. Lanteigne, D. P. Overy, R. G. Kerr, A. Thompson, Antimicrobial activity of non-natural prodigiosenes, RSC Advances, 3 (2013) 22967–22971.
P. Rawat, R. N. Singh, A. Ranjan, A. Gautam, S. Trivedi, M. Kumar, Study of antimicrobial and antioxidant activities of pyrrole-chalcones, J. Mol. Struct., 1228 (2021) 129483–129494.
Z. H. Bulbul, T. S. Chowdhury, M. H. Misbah, J. Ferdous, S. Dey, I. Hasan, Y. Fujii, Y. Ozeki, S. M. A. Kawsar, Synthesis of new series of pyrimidine nucleoside derivatives bearing the acyl moieties as potential antimicrobial agents, Pharmacia, 68(1) (2021) 23–34.
S. C. Tasneem, J. Ferdous, M. Z. H. Bulbul, M. M. H. Misbah, D. Sujan, I. Hasan, S. M. A. Kawsar, Antimicrobial and anticancer activities of some partially acylated thymidine derivatives, J. Bio-Sci., 29(1) (2021) 11–22.

Details

Primary Language

English

Subjects

Macromolecular and Materials Chemistry (Other)

Journal Section

Research Article

Authors

Seda Çınar ^*
0000-0001-6591-7141
Türkiye

Dilek Işık Taşgın
0000-0002-0316-4604
Türkiye

Nalan Oya San Keskin
0000-0001-6645-3561
Türkiye

Publication Date

October 1, 2025

Submission Date

June 30, 2025

Acceptance Date

September 29, 2025

Published in Issue

Year 2025 Volume: 53 Number: 4

DOI

https://doi.org/10.15671/hjbc.1731070

IZ

https://izlik.org/JA35RL45JA

Cite

RIS / Bibtex

APA

Çınar, S., Işık Taşgın, D., & San Keskin, N. O. (2025). Synthesis of novel meso-ester oligopyrroles and evaluation of their antibacterial activities. Hacettepe Journal of Biology and Chemistry, 53(4), 67-73. https://doi.org/10.15671/hjbc.1731070

AMA

1.Çınar S, Işık Taşgın D, San Keskin NO. Synthesis of novel meso-ester oligopyrroles and evaluation of their antibacterial activities. HJBC. 2025;53(4):67-73. doi:10.15671/hjbc.1731070

Chicago

Çınar, Seda, Dilek Işık Taşgın, and Nalan Oya San Keskin. 2025. “Synthesis of Novel Meso-Ester Oligopyrroles and Evaluation of Their Antibacterial Activities”. Hacettepe Journal of Biology and Chemistry 53 (4): 67-73. https://doi.org/10.15671/hjbc.1731070.

EndNote

Çınar S, Işık Taşgın D, San Keskin NO (October 1, 2025) Synthesis of novel meso-ester oligopyrroles and evaluation of their antibacterial activities. Hacettepe Journal of Biology and Chemistry 53 4 67–73.

IEEE

[1]S. Çınar, D. Işık Taşgın, and N. O. San Keskin, “Synthesis of novel meso-ester oligopyrroles and evaluation of their antibacterial activities”, HJBC, vol. 53, no. 4, pp. 67–73, Oct. 2025, doi: 10.15671/hjbc.1731070.

ISNAD

Çınar, Seda - Işık Taşgın, Dilek - San Keskin, Nalan Oya. “Synthesis of Novel Meso-Ester Oligopyrroles and Evaluation of Their Antibacterial Activities”. Hacettepe Journal of Biology and Chemistry 53/4 (October 1, 2025): 67-73. https://doi.org/10.15671/hjbc.1731070.

JAMA

1.Çınar S, Işık Taşgın D, San Keskin NO. Synthesis of novel meso-ester oligopyrroles and evaluation of their antibacterial activities. HJBC. 2025;53:67–73.

MLA

Çınar, Seda, et al. “Synthesis of Novel Meso-Ester Oligopyrroles and Evaluation of Their Antibacterial Activities”. Hacettepe Journal of Biology and Chemistry, vol. 53, no. 4, Oct. 2025, pp. 67-73, doi:10.15671/hjbc.1731070.

Vancouver

1.Seda Çınar, Dilek Işık Taşgın, Nalan Oya San Keskin. Synthesis of novel meso-ester oligopyrroles and evaluation of their antibacterial activities. HJBC. 2025 Oct. 1;53(4):67-73. doi:10.15671/hjbc.1731070