Bromotyrosine derivatives from marine sponges inhibit the HIV-1 replication in vitro

Authors

DOI:

https://doi.org/10.17533/udea.vitae.16797

Keywords:

HIV-1, marine resoruces, antiviral activity, bromotyrosine, marine sponge

Abstract

Background: Human immunodeficiency virus type 1 (HIV-1) infection and Acquired immunodeficiency syndrome are mayor global public health issues. HIV-1 infection is now manageable as a chronic disease thanks to the development of antiretroviral therapy; however, the existence of HIV drug resistance and collateral effects have increased the search for therapeutic alternatives. Compounds of marine resources have been studied for their antiviral potential. Objectives: To evaluate the antiviral activity of isolated bromotyrosine-derivative compounds from the Colombian marine sponges, Verongula rigida and Aiolochoria crassa against HIV-1 infection in vitro. Methods: Cytotoxicity of 11 bromotyrosine-derivative compounds was determined by the MTT assay. Inhibition of HIV-1 replication was performed using the U373-MAGI cell line, which was infected with recombinant green fluorescent protein (GFP)-expressing viruses pseudotyped, in the presence or absence of the compounds. The percentage of infected cells was evaluated by flow cytometry. In addition, the inhibition of reverse transcription and nuclear import was determined by quantification of early and late reverse transcription products and 2-LTR circles, respectively, using quantitative PCR. Results: Aeroplysinin-1, purealidin B and 3-bromo-5-hydroxy-Omethyltyrosine inhibited the HIV-1 replication in a dose-dependent manner, with a median maximum percentage of inhibition of 74% (20 μM), 57% (80 μM) and 47% (80 μM), respectively. Importantly, none of these concentrations were cytotoxic. Aeroplysinin-1, 19-deoxyfistularin 3, purealidin B, fistularin 3 and 3-bromo-5-hydroxy-O-methyltyrosine inhibited the nuclear import efficiently; while 3,5-dibromo-N,N,N,O-tetramethyltyraminium, aeroplysinin-1, purealidin B, fistularin 3 and 3-bromo-5-hydroxy-Omethyltyrosine inhibited X4 HIV-1 cell entry with a median maximum percentage of inhibition ranging between 2 to 30%. Conclusions: Aeroplysinin-1, 19-deoxyfistularin 3, purealidin B, fistularin 3 and 3-bromo-5-hydroxy-O-methyltyrosine inhibited HIV replication at different steps. This study opens the possibility of chemically synthesizing these compounds and evaluating them as alternative therapies against HIV-1.

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Author Biographies

Leon Gabriel GÓMEZ-ARCHILA, Universidad de Antioquia

Faculty of Medicine, Immunovirology Group, QF

Wildeman ZAPATA, Universidad de Antioquia / Universidad Cooperativa de Colombia

Faculty of Medicine, Immunovirology Group / Faculty of Medicine, Infettare Group. PhD

Elkin GALEANO, Universidad de Antioquia

Faculty of Pharmaceutical Chemistry, Marine Natural Products Group, PhD

Alejandro MARTÍNEZ, Universidad de Antioquia

Faculty of Pharmaceutical Chemistry, Marine Natural Products Group, PhD

Francisco Javier DÍAZ CASTRILLÓN, Universidad de Antioquia

Faculty of Medicine, Immunovirology Group, QF

María Teresa RUGELES, Universidad de Antioquia

Faculty of Medicine, Immunovirology Group

References

Joint United Nations Programme on HIV/AIDS (UNAIDS). UNAIDS report on the global AIDS epidemic 2012. Geneva, Switzerland: WHO Library Cataloguing-in-Publication Data; 2012 Nov 20. 110 p.

Lehrman G, Hogue I, Palmer S, Jennings C, Spina C, Wiegand A, et al. Depletion of latent HIV-1 infection in vivo: a proof-ofconcept study. The Lancet. 2005; 366 (9485): 549-555.

Stekler J, Maenza J, Stevens C, Holte S, Malhotra U, McElrath MJ, et al. Abacavir hypersensitivity reaction in primary HIV infection. Aids. 2006; 20: 1269-1274.

Sundaram M, Saghayam S, Priya B, Venkatesh KK, Balakrishnan P, Shankar EM, et al. Changes in antioxidant profile among HIV-infected individuals on generic highly active antiretroviral therapy in southern India. Int J Infect Dis. 2008; 12: 61-66.

Kolber MA, Saenz MO, Tanner TJ, Arheart KL, Pahwa S, Liu H. Intensification of a suppressive HAART regimen increases CD4 counts and decreases CD8+ T-cell activation. Clin Immunol. 2008; 126: 315-321.

Ford PW, Gustafson KR, McKee TC, Shigematsu N, Maurizi LK, Pannell LK, et al. Papuamides A-D, HIV-inhibitory and cytotoxic depsipeptides form the sponges Theonella mirabilis and Theonella swinhoei collected in Papua New Guinea. J Am Chem Soc. 1999; 121: 5899-5909.

Qureshi A, Faulkner DJ. Haplosamates A and B: new steroidal sulfamate esters from two haploclerid sponges. Tetrahedron. 1999; 55: 8323-8330.

Rudi A, Yosief T, Loya S, Hizi A, Schleyer M, Kashman Y. Clathsterol, a novel anti-HIV-1 RT sulfated sterol from the

sponge Clathria species. J Nat Prod. 2001; 64: 1451-1453.

O’Keefe BR, Erim T, Beutler JA, Cardellina II JH, Gulakowski RJ, Krepps BL, et al. Isolation and characterization of adociavirin, a novel HIV-inhibitory protein from the sponge Adocia sp. FEBS Letters. 1998 Jul 10; 431 (1): 85-90.

Arts EJ, Hazuda DJ. HIV-1 Antiretroviral Drug Therapy. Cold Spring Harb Perspect Med. 2012; 2 (4): a007161.

Ana SE, Marisa N, Madalena H, Joao G. Sulfated Polysaccharides in Marine Sponges: Extraction Methods and Anti-HIV Activity. Mar Drugs. 2011; 9(1): 139-153.

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Published

21-07-2014

How to Cite

GÓMEZ-ARCHILA, L. G., ZAPATA, W., GALEANO, E., MARTÍNEZ, A., DÍAZ CASTRILLÓN, F. J., & RUGELES, M. T. (2014). Bromotyrosine derivatives from marine sponges inhibit the HIV-1 replication in vitro. Vitae, 21(2), 114–125. https://doi.org/10.17533/udea.vitae.16797

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Section

Natural Products

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