Synthesis and biological comparison of two antimicrobial peptides originated from the venom of Vespa crabro and Polybia paulista

Le Huy Binh; Bui Thi Phuong Hai; Do Hai Yen; Trinh Thi Kim Anh; Nguyen Hong Minh; Nguyen Thi Thanh Binh; Luong Xuan Huy; Vu Dinh Hoang

doi:10.15625/2525-2518/18128

Author affiliations

Authors

Le Huy Binh Center For High Technology Development, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay District, Ha Noi, Viet Nam
Bui Thi Phuong Hai Faculty of Pharmacy, PHENIKAA University, Nguyen Trac Street, Ha Dong District, Ha Noi, Viet Nam
Do Hai Yen Faculty of Pharmacy, PHENIKAA University, Nguyen Trac Street, Ha Dong District, Ha Noi, Viet Nam https://orcid.org/0009-0001-5416-1737
Trinh Thi Kim Anh Faculty of Pharmacy, PHENIKAA University, Nguyen Trac Street, Ha Dong District, Ha Noi, Viet Nam
Nguyen Hong Minh Bioresource Research Center, PHENIKAA University, Nguyen Trac Street, Ha Dong District, Ha Noi, Viet Nam https://orcid.org/0000-0002-4252-8319
Nguyen Thi Thanh Binh VNU University of Medicine and Pharmacy, 144 Xuan Thuy, Cau Giay District, Ha Noi, Viet Nam
Luong Xuan Huy Faculty of Pharmacy, PHENIKAA University, Nguyen Trac Street, Ha Dong District, Ha Noi, Viet Nam; PHENIKAA Institute for Advanced Study (PIAS), PHENIKAA University, Nguyen Trac Street, Ha Dong District, Ha Noi, Viet Nam https://orcid.org/0000-0003-4815-006X
Vu Dinh Hoang School of Chemical Engineering - Hanoi University of Science and Technology, 1 Dai Co Viet, Hai Ba Trung District, Ha Noi, Viet Nam https://orcid.org/0000-0002-2112-6732

DOI:

https://doi.org/10.15625/2525-2518/18128

Keywords:

Antimicrobial peptides, natural peptides, bee venom, antifungal agents, structural-activity relationships

Abstract

Mastoparan C and Polybia-MP1 are two well-known AMPs found in the European Hornet Vespa crabro and social wasåp Polybia paulista, respectively. Due to the potent antimicrobial activity toward a wide range of microbial pathogens, including Gram-negative, Gram-positive and fungal species, they are promising to tackle the global antimicrobial resistance crisis. Thus, understanding the structure and activity relationships (SARs) is essential for the development of potential therapeutic applications. In this study, we prepared Mastoparan C and Polybia-MP1 and investigated the differences in their biological properties. Both AMPs were successfully synthesized and purified with more than 95% purity, confirmed by high-performance liquid chromatography and mass spectrometry. Besides, the data indicated a decrease in antimicrobial activity but notably less hemolysis of MP1 compared to MPC. Overall, our study suggests various important information regarding the structural requirements for the antimicrobial and hemolytic activity of antimicrobial peptides.

Downloads

Download data is not yet available.

References

Venkatesan P. - WHO 2020 report on the antibacterial production and development pipeline, The Lancet Microbe 2 (2021) e239.

Organization W. H. - 2019 antibacterial agents in clinical development: an analysis of the antibacterial clinical development pipeline, 2019.

Luong H. X., Thanh T. T., Tran T. H. - Antimicrobial peptides – Advances in development of therapeutic applications, Life Sci. 260 (2020) 118407.

Luong H. X., Ngan H. D., Thi Phuong H. B., Quoc T. N., Tung T. T. - Multiple roles of ribosomal antimicrobial peptides in tackling global antimicrobial resistance, R. Soc. Open Sci. 9 (1) 211583.

Souza B. M., Mendes M. A., Santos L. D., Marques M. R., César L. M. M., Almeida R. N. A., Pagnocca F. C., Konno K., Palma M. S. - Structural and functional characterization of two novel peptide toxins isolated from the venom of the social wasp Polybia paulista, Peptides 26 (11) (2005) 2157-2164.

Luong H. X., Kim D. H., Lee B. J., Kim Y. W. - Antimicrobial activity and stability of stapled helices of polybia-MP1, Arch. Pharm. Res. 40 (12) (2017) 1414-1419.

Xuan H. L., Duc T. D., Thuy A. M., Chau P. M., Tung T. T. - Chemical approaches in the development of natural nontoxic peptide Polybia-MP1 as a potential dual antimicrobial and antitumor agent, Amino Acids 53 (6) (2021) 843-852.

Shah P., Shrivastava S., Gogoi P., Saxena S., Srivastava S., Singh R. J., Godara B., Kumar N., Gaur G. K. - Wasp Venom Peptide (Polybia MP-1) Shows Antimicrobial Activity Against Multi Drug Resistant Bacteria Isolated from Mastitic Cow Milk, International Journal of Peptide Research and Therapeutics 28 (1) (2022) 44.

Argiolas A., Pisano J. J. - Isolation and characterization of two new peptides, mastoparan C and crabrolin, from the venom of the European hornet, Vespa crabro, Journal of Biological Chemistry 259 (16) (1984) 10106-10111.

Yoon K. A., Kim K., Nguyen P., Seo J. B., Park Y. H., Kim K. G., Seo H. Y., Koh Y. H., Lee S. H. - Comparative bioactivities of mastoparans from social hornets Vespa crabro and Vespa analis, Journal of Asia-Pacific Entomology 18 (4) (2015) 825-829.

Baek J. H., Ji Y., Shin J. S., Lee S., Lee S. H. - Venom peptides from solitary hunting wasps induce feeding disorder in lepidopteran larvae. Peptides, 32 (3) (2011) 568-572.

Chen X., Zhang L., Wu Y., Wang L., Ma C., Xi X., Bininda-Emonds O. R. P., Shaw C., Chen T., Zhou M. - Evaluation of the bioactivity of a mastoparan peptide from wasp venom and of its analogues designed through targeted engineering, Int. J. Biol. Sci. 14 (6) (2018) 599-607.

Thi Phuong Hai B., Thi Kim Anh T., Thi Khanh Huyen T., Xuan Huy L., Thi Ngan D., Thi Thuong B., Van Khanh N., Thanh Hai N., Thi Thanh Binh N. - Potentialities of Antimicrobial Peptide Mastoparan C Isolated the European Hornet Vespa Crabro in Drug Discovery, JS: MPS 39 (1) (2023) 10-19.

Phuong H. B. T., Tran V. A., Ngoc K. N., Huu V. N., Thu H. N., Van M. C., Thi H. P., Hong M. N., Tran H. T., Xuan H. L. - Effect of substituting glutamine with lysine on structural and biological properties of antimicrobial peptide Polybia-MP1, Amino Acids 55 (2023) 881-890

Luong H. X., Bui H. T. P., Tung T. T. - Application of the All-Hydrocarbon Stapling Technique in the Design of Membrane-Active Peptides, J. Med. Chem. 65 (4) (2022) 3026-3045.

Alvares D. S., Wilke N., Ruggiero Neto J., Fanani M. L. - The insertion of Polybia-MP1 peptide into phospholipid monolayers is regulated by its anionic nature and phase state, Chem. Phys. Lipids 207 (2017) 38-48.

Alvares D. S., Fanani M. L., Ruggiero Neto J., Wilke N. - The interfacial properties of the peptide Polybia-MP1 and its interaction with DPPC are modulated by lateral electrostatic attractions. Biochim, Biophys. Acta - Biomembr. 1858 (2) (2016) 393-402.

dos Santos Cabrera M. P., Arcisio-Miranda M., Gorjão R., Leite N. B., de Souza B. M., Curi R., Procopio J., Ruggiero Neto J., Palma M. S. - Influence of the Bilayer Composition on the Binding and Membrane Disrupting Effect of Polybia-MP1, an Antimicrobial Mastoparan Peptide with Leukemic T-Lymphocyte Cell Selectivity, Biochemistry 51 (24) (2012) 4898-4908.

Zhu N., Zhong C., Liu T., Zhu Y., Gou S., Bao H., Yao J., Ni J. - Newly designed antimicrobial peptides with potent bioactivity and enhanced cell selectivity prevent and reverse rifampin resistance in Gram-negative bacteria, Eur. J. Pharm. Sci. 158 (2021) 105665.

Gautier R., Douguet D., Antonny B., Drin G. - HELIQUEST: a web server to screen sequences with specific α-helical properties, Bioinform. 24 (18) (2008) 2101-2102.

Luong H. X., Kim D. H., Lee B. J., Kim Y. W. - Antimicrobial and Hemolytic Activity of Stapled Heptapeptide Dimers, Bull. Kor. Chem. Soc. 37 (8) (2016) 1199-1203.

Coin I., Beyermann M., Bienert M. - Solid-phase peptide synthesis: from standard procedures to the synthesis of difficult sequences, Nat. Protoc. 2 (12) (2007) 3247-3256.

Kim Y. W., Grossmann T. N., Verdine G. L. - Synthesis of all-hydrocarbon stapled α-helical peptides by ring-closing olefin metathesis, Nat. Protoc. 6 (6) (2011) 761-771.

El-Faham A., Albericio F. - COMU: A third generation of uronium-type coupling reagents, J. Pep. Sci. 16 (1) (2010) 6-9.

El-Faham A., Funosas R. S., Prohens R., Albericio F. - COMU: A Safer and More Effective Replacement for Benzotriazole-Based Uronium Coupling Reagents, Chem. – Eur. J. 15 (37) (2009) 9404-9416.

de Santana C. J. C., Pires Júnior O. R., Fontes W., Palma M. S., Castro M. S. - Mastoparans: A Group of Multifunctional α-Helical Peptides With Promising Therapeutic Properties, Front. Mol. Biosci. 9 (2022)

dos Santos Cabrera M. P., Costa S. T. B., de Souza B. M., Palma M. S., Ruggiero J. R., Ruggiero Neto J. - Selectivity in the mechanism of action of antimicrobial mastoparan peptide Polybia-MP1, Eur. Biophys. J. 37 (6) (2008) 879.

Leite N. B., da Costa L. C., dos Santos Alvares D., dos Santos Cabrera M. P., de Souza B. M., Palma M. S., Ruggiero Neto J. - The effect of acidic residues and amphipathicity on the lytic activities of mastoparan peptides studied by fluorescence and CD spectroscopy, Amino Acids 40 (1) (2011) 91-100.

Leite N. B., dos Santos Alvares D., de Souza B. M., Palma M. S., Ruggiero Neto J. - Effect of the aspartic acid D2 on the affinity of Polybia-MP1 to anionic lipid vesicles, Eur. Biophys. J. 43 (4) (2014) 121-130.