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Alexandra Ibáñez-Escribano
Departamento de Microbiología y Parasitología, Facultad de Farmacia, Universidad Complutense de Madrid (UCM), Plaza Ramón y Cajal s/n, 28040 Madrid, Spain

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Short communication
Published: 05 February 2021 in Bioorganic & Medicinal Chemistry Letters
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A series of 11 3-(ω-aminoalkoxy)-1-benzyl-5-nitroindazoles (2–12) has been prepared starting from 1-benzyl-5-nitroindazol-3-ol 13, and evaluated against sensitive and resistant isolates of the sexually transmitted protozoan Trichomonas vaginalis. Compounds 2, 3, 6, 9, 10 and 11 showed trichomonacidal profiles with IC50 < 20 µM against the metronidazole-sensitive isolate. Moreover, all these compounds submitted to cytotoxicity assays against mammalian cells exhibited low non-specific cytotoxic effects, except compounds 3 and 9 which displayed moderate cytotoxicity (CC50 = 74.7 and 59.1 µM, respectively). Those compounds with trichomonacidal effect were also evaluated against a metronidazole-resistant culture. Special mention deserve compounds 6 and 10, which displayed better IC50 values (1.3 and 0.5 µM respectively) than that of the reference drug (IC50 MTZ = 3.0 µM). The high activity of these compounds against the resistant isolate reinforces the absence of cross-resistance with the reference drug. The remarkable trichomonacidal results against resistant T. vaginalis isolates suggest the interest of 3-(ω-aminoalkoxy)-1-benzyl-5-nitroindazoles to be considered as good prototypes to continue in the development of new drugs with enhanced trichomonacidal activity, aiming to increase the non-existent drugs to face clinical resistance efficiently for those patients in whom therapy with 5-nitroimidazoles is contraindicated.

ACS Style

Alexandra Ibáñez-Escribano; Felipe Reviriego; Nerea Vela; Cristina Fonseca-Berzal; Juan José Nogal-Ruiz; Vicente J. Arán; José Antonio Escario; Alicia Gómez-Barrio. Promising hit compounds against resistant trichomoniasis: Synthesis and antiparasitic activity of 3-(ω-aminoalkoxy)-1-benzyl-5-nitroindazoles. Bioorganic & Medicinal Chemistry Letters 2021, 37, 127843 .

AMA Style

Alexandra Ibáñez-Escribano, Felipe Reviriego, Nerea Vela, Cristina Fonseca-Berzal, Juan José Nogal-Ruiz, Vicente J. Arán, José Antonio Escario, Alicia Gómez-Barrio. Promising hit compounds against resistant trichomoniasis: Synthesis and antiparasitic activity of 3-(ω-aminoalkoxy)-1-benzyl-5-nitroindazoles. Bioorganic & Medicinal Chemistry Letters. 2021; 37 ():127843.

Chicago/Turabian Style

Alexandra Ibáñez-Escribano; Felipe Reviriego; Nerea Vela; Cristina Fonseca-Berzal; Juan José Nogal-Ruiz; Vicente J. Arán; José Antonio Escario; Alicia Gómez-Barrio. 2021. "Promising hit compounds against resistant trichomoniasis: Synthesis and antiparasitic activity of 3-(ω-aminoalkoxy)-1-benzyl-5-nitroindazoles." Bioorganic & Medicinal Chemistry Letters 37, no. : 127843.

Protozoology original paper
Published: 14 May 2020 in Parasitology Research
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Trichomoniasis is the most prevalent curable sexually transmitted infection (STI) worldwide and a risk factor for the acquisition of other STIs and adverse pregnancy outcomes. The objectives of this study were to determine the prevalence of T. vaginalis and related coinfections in women attending a third-level hospital of Madrid (Spain). A retrospective study of 24,173 vaginal exudates from women with suspected vaginitis was conducted between 2013 and 2017. Likewise, among T. vaginalis positive samples, co-occurrence with gonorrhea, chlamydia, syphilis, VIH, Mycoplasma hominis, and Ureaplasma urealyticum was checked. Moreover, seven T. vaginalis isolates from 2017 were randomly collected for endobionts, drug resistance, and microsatellite (MS) instability determinations. The prevalence of T. vaginalis was 0.8% between 2013 and 2017. Less than 20% of patients with trichomoniasis were submitted to a complete screening for other genital pathogens. From that, two patients were coinfected with chlamydia and three with syphilis. Surprisingly, 6.4% of positive samples were diagnosed among pregnant women, showing an alarming increase from 3.2% (2014) to 10% (2017). Among the isolates randomly analyzed, five carried T. vaginalis virus, five harbored mycoplasmas, and one was metronidazole-resistant. The molecular genotyping showed a high variability in the three MS evaluated. To our knowledge, this is the first study in Spain that evaluates the prevalence of trichomoniasis in general and pregnant population and includes biomolecular determinations. These results warn about the increasing prevalence and highlight the importance of including T. vaginalis detection in routine gynecological revisions with special emphasis on childbearing age women and patients with previous STIs.

ACS Style

Celia Bolumburu; Vega Zamora; María Muñoz-Algarra; Francisca Portero-Azorín; José Antonio Escario; Alexandra Ibáñez-Escribano. Trichomoniasis in a tertiary hospital of Madrid, Spain (2013–2017): prevalence and pregnancy rate, coinfections, metronidazole resistance, and endosymbiosis. Parasitology Research 2020, 119, 1915 -1923.

AMA Style

Celia Bolumburu, Vega Zamora, María Muñoz-Algarra, Francisca Portero-Azorín, José Antonio Escario, Alexandra Ibáñez-Escribano. Trichomoniasis in a tertiary hospital of Madrid, Spain (2013–2017): prevalence and pregnancy rate, coinfections, metronidazole resistance, and endosymbiosis. Parasitology Research. 2020; 119 (6):1915-1923.

Chicago/Turabian Style

Celia Bolumburu; Vega Zamora; María Muñoz-Algarra; Francisca Portero-Azorín; José Antonio Escario; Alexandra Ibáñez-Escribano. 2020. "Trichomoniasis in a tertiary hospital of Madrid, Spain (2013–2017): prevalence and pregnancy rate, coinfections, metronidazole resistance, and endosymbiosis." Parasitology Research 119, no. 6: 1915-1923.

Journal article
Published: 22 April 2019 in Toxins
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Cantharidin (CTD) is a toxic monoterpene produced by blister beetles (Fam. Meloidae) as a chemical defense against predators. Although CTD is highly poisonous to many predator species, some have evolved the ability to feed on poisonous Meloidae, or otherwise beneficially use blister beetles. Great Bustards, Otis tarda, eat CTD-containing Berberomeloe majalis blister beetles, and it has been hypothesized that beetle consumption by these birds reduces parasite load (a case of self-medication). We examined this hypothesis by testing diverse organisms against CTD and extracts of B. majalis hemolymph and bodies. Our results show that all three preparations (CTD and extracts of B. majalis) were toxic to a protozoan (Trichomonas vaginalis), a nematode (Meloidogyne javanica), two insects (Myzus persicae and Rhopalosiphum padi) and a tick (Hyalomma lusitanicum). This not only supports the anti-parasitic hypothesis for beetle consumption, but suggests potential new roles for CTD, under certain conditions.

ACS Style

Douglas W. Whitman; Maria Fe Andrés; Rafael A. Martínez-Díaz; Alexandra Ibáñez-Escribano; A. Sonia Olmeda; Azucena González-Coloma; Martínez- Díaz; Ibáñez- Escribano; González- Coloma. Antiparasitic Properties of Cantharidin and the Blister Beetle Berberomeloe majalis (Coleoptera: Meloidae). Toxins 2019, 11, 234 .

AMA Style

Douglas W. Whitman, Maria Fe Andrés, Rafael A. Martínez-Díaz, Alexandra Ibáñez-Escribano, A. Sonia Olmeda, Azucena González-Coloma, Martínez- Díaz, Ibáñez- Escribano, González- Coloma. Antiparasitic Properties of Cantharidin and the Blister Beetle Berberomeloe majalis (Coleoptera: Meloidae). Toxins. 2019; 11 (4):234.

Chicago/Turabian Style

Douglas W. Whitman; Maria Fe Andrés; Rafael A. Martínez-Díaz; Alexandra Ibáñez-Escribano; A. Sonia Olmeda; Azucena González-Coloma; Martínez- Díaz; Ibáñez- Escribano; González- Coloma. 2019. "Antiparasitic Properties of Cantharidin and the Blister Beetle Berberomeloe majalis (Coleoptera: Meloidae)." Toxins 11, no. 4: 234.

Journal article
Published: 22 May 2018 in ChemMedChem
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Three different series of new 5-nitroindazole derivatives-1-(ω-aminoalkyl)-2-benzylindazolin-3-ones (series A; ten compounds), 3-(ω-aminoalkoxy)-2-benzylindazoles (series B; four compounds) and 3-alkylamino-2-benzylindazoles (series C; five compounds)-have been synthesized and evaluated against the protozoan parasites Trypanosoma cruzi, Leishmania amazonensis, and Trichomonas vaginalis: etiological agents of Chagas disease, cutaneous leishmaniasis, and trichomoniasis, respectively. Many indazoles of series A, B, and C were efficient against T. cruzi. Some compounds in series A, after successfully passing the preliminary screening for epimastigotes, exhibited activity values against amastigotes of several T. cruzi strains that were better than or similar to those shown by the reference drug benznidazole and displayed low nonspecific toxicity against mammalian cells. On the other hand, preliminary studies against promastigotes of L. amazonensis showed high leishmanicidal activity for some derivatives of series A and C. With regard to activity against T. vaginalis, some indazoles of series B and C were rather efficient against trophozoites of a metronidazole-sensitive isolate and showed low nonspecific toxicities toward Vero cell cultures. Additionally, some of these compounds displayed similar activity against metronidazole-sensitive and resistant isolates, showing the absence of cross-resistance between these derivatives and the reference drug.

ACS Style

Cristina Fonseca-Berzal; Alexandra Ibáñez-Escribano; Nerea Vela; José Cumella; Juan José Nogal-Ruiz; José Antonio Escario; Patrícia Bernardino Da Silva; Marcos Meuser Batista; Maria De Nazaré C. Soeiro; Sergio Sifontes-Rodríguez; Alfredo Meneses-Marcel; Alicia Gómez-Barrio; Vicente J. Arán. Antichagasic, Leishmanicidal, and Trichomonacidal Activity of 2-Benzyl-5-nitroindazole-Derived Amines. ChemMedChem 2018, 13, 1246 -1259.

AMA Style

Cristina Fonseca-Berzal, Alexandra Ibáñez-Escribano, Nerea Vela, José Cumella, Juan José Nogal-Ruiz, José Antonio Escario, Patrícia Bernardino Da Silva, Marcos Meuser Batista, Maria De Nazaré C. Soeiro, Sergio Sifontes-Rodríguez, Alfredo Meneses-Marcel, Alicia Gómez-Barrio, Vicente J. Arán. Antichagasic, Leishmanicidal, and Trichomonacidal Activity of 2-Benzyl-5-nitroindazole-Derived Amines. ChemMedChem. 2018; 13 (12):1246-1259.

Chicago/Turabian Style

Cristina Fonseca-Berzal; Alexandra Ibáñez-Escribano; Nerea Vela; José Cumella; Juan José Nogal-Ruiz; José Antonio Escario; Patrícia Bernardino Da Silva; Marcos Meuser Batista; Maria De Nazaré C. Soeiro; Sergio Sifontes-Rodríguez; Alfredo Meneses-Marcel; Alicia Gómez-Barrio; Vicente J. Arán. 2018. "Antichagasic, Leishmanicidal, and Trichomonacidal Activity of 2-Benzyl-5-nitroindazole-Derived Amines." ChemMedChem 13, no. 12: 1246-1259.

Abstract
Published: 01 January 2017 in Proceedings
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Note: In lieu of an abstract, this is an excerpt from the first page. Edelfosine (ET-18-OCH3) is an alkylphospholipid with an analogous structure to miltefosine. Both molecules are active against kinetoplastids (Leishmania spp., Trypanosoma cruzi and Trypanosoma brucei).

ACS Style

Alexandra Ibáñez-Escribano; Jose Antonio Escario; Faustino Mollinedo; Alicia Gómez-Barrio. Edelfosine (ET-18-OCH3) a Promising Alkylphospholipid against Resistant Trichomonas vaginalis. Proceedings 2017, 1, 653 .

AMA Style

Alexandra Ibáñez-Escribano, Jose Antonio Escario, Faustino Mollinedo, Alicia Gómez-Barrio. Edelfosine (ET-18-OCH3) a Promising Alkylphospholipid against Resistant Trichomonas vaginalis. Proceedings. 2017; 1 (6):653.

Chicago/Turabian Style

Alexandra Ibáñez-Escribano; Jose Antonio Escario; Faustino Mollinedo; Alicia Gómez-Barrio. 2017. "Edelfosine (ET-18-OCH3) a Promising Alkylphospholipid against Resistant Trichomonas vaginalis." Proceedings 1, no. 6: 653.

Abstract
Published: 01 January 2017 in Proceedings
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Note: In lieu of an abstract, this is an excerpt from the first page.Excerpt New, safe, well tolerated, and versatile anti-trichomonal agents for oral and topical use are needed to combat spreading resistance of Trichomonas vaginalis to metronidazole (MTZ).

ACS Style

Alexandra Ibáñez-Escribano; Leyre Pernaute Lau; Juan José Nogal-Ruiz; Alicia Gómez-Barrio; Jose Antonio Escario; Michael A. Zeligs. Trichomonacidal Activity of 3,3′-Diindolylmethane (DIM) Is Additive to Metronidazole (MTZ) In Vitro, Supporting Future Oral/Topical Use. Proceedings 2017, 1, 645 .

AMA Style

Alexandra Ibáñez-Escribano, Leyre Pernaute Lau, Juan José Nogal-Ruiz, Alicia Gómez-Barrio, Jose Antonio Escario, Michael A. Zeligs. Trichomonacidal Activity of 3,3′-Diindolylmethane (DIM) Is Additive to Metronidazole (MTZ) In Vitro, Supporting Future Oral/Topical Use. Proceedings. 2017; 1 (6):645.

Chicago/Turabian Style

Alexandra Ibáñez-Escribano; Leyre Pernaute Lau; Juan José Nogal-Ruiz; Alicia Gómez-Barrio; Jose Antonio Escario; Michael A. Zeligs. 2017. "Trichomonacidal Activity of 3,3′-Diindolylmethane (DIM) Is Additive to Metronidazole (MTZ) In Vitro, Supporting Future Oral/Topical Use." Proceedings 1, no. 6: 645.

Journal article
Published: 04 November 2015 in Parasitology
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SUMMARYA selection of 1,2-disubstituted 5-nitroindazolin-3-ones (1–19) and 3-alkoxy-5-nitroindazoles substituted at positions 1 (20–24) or 2 (25–39) from our in-house compound library were screened in vitro against the most common curable sexually transmitted pathogen, Trichomonas vaginalis. A total of 41% of the studied molecules (16/39) achieved a significant activity of more than 85% growth inhibition at the highest concentration assayed (100 µg mL−1). Among these compounds, 3-alkoxy-5-nitroindazole derivatives 23, 24, 25 and 27 inhibited parasite growth by more than 50% at 10 µg mL−1. In addition, the first two compounds (23, 24) still showed remarkable activity at the lowest dose tested (1 µg mL−1), inhibiting parasite growth by nearly 40%. Their specific activity towards the parasite was corroborated by the determination of their non-specific cytotoxicity against mammalian cells. The four mentioned compounds exhibited non-cytotoxic profiles at all of the concentrations assayed, showing a fair antiparasitic selectivity index (SI > 7·5). In silico studies were performed to predict pharmacokinetic properties, toxicity and drug-score using Molinspiration and OSIRIS computational tools. The current in vitro results supported by the virtual screening suggest 2-substituted and, especially, 1-substituted 3-alkoxy-5-nitroindazoles as promising starting scaffolds for further development of novel chemical compounds with the main aim of promoting highly selective trichomonacidal lead-like drugs with adequate pharmacokinetic and toxicological profiles.

ACS Style

Alexandra Ibáñez-Escribano; Juan José Nogal-Ruiz; Alicia Gómez-Barrio; Vicente J. Arán; José Antonio Escario. In vitro trichomonacidal activity and preliminary in silico chemometric studies of 5-nitroindazolin-3-one and 3-alkoxy-5-nitroindazole derivatives. Parasitology 2015, 143, 34 -40.

AMA Style

Alexandra Ibáñez-Escribano, Juan José Nogal-Ruiz, Alicia Gómez-Barrio, Vicente J. Arán, José Antonio Escario. In vitro trichomonacidal activity and preliminary in silico chemometric studies of 5-nitroindazolin-3-one and 3-alkoxy-5-nitroindazole derivatives. Parasitology. 2015; 143 (1):34-40.

Chicago/Turabian Style

Alexandra Ibáñez-Escribano; Juan José Nogal-Ruiz; Alicia Gómez-Barrio; Vicente J. Arán; José Antonio Escario. 2015. "In vitro trichomonacidal activity and preliminary in silico chemometric studies of 5-nitroindazolin-3-one and 3-alkoxy-5-nitroindazole derivatives." Parasitology 143, no. 1: 34-40.

Journal article
Published: 01 September 2015 in Acta Tropica
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Trichomonas vaginalis is known to evade complement-mediated lysis. Because the genome of T. vaginalis does not possess DNA sequence with homology to human protectin (CD59), a complement lysis restricting factor, we tested the hypothesis that host CD59 acquisition by T. vaginalis organisms mediates resistance to complement killing. This hypothesis was based on the fact that trichomonads are known to associate with host proteins. No CD59 was detected on the surface of T. vaginalis grown in serum-based medium using as probe anti-CD59 monoclonal antibody (MAb). We, therefore, infected mice intraperitoneally with live T. vaginalis, and trichomonads harvested from ascites were tested for binding of CD59. Immunofluorescence showed that parasites had surface CD59. Furthermore, as mouse erythrocytes (RBCs) possess membrane-associated CD59, and trichomonads use RBCs as a nutrient source, organisms were co-cultured with murine RBCs for one week. Parasites were shown to have detectable surface CD59. Importantly, live T. vaginalis with bound CD59 were compared with batch-grown parasites without surface-associated CD59 for sensitivity to complement in human serum. Trichomonads without surface-bound CD59 had a higher level of killing by complement than did parasites with surface CD59. These data show that host CD59 acquired onto the surface by live T. vaginalis may be an alternative mechanism for complement evasion. We describe a novel strategy by T. vaginalis consistent with host protein procurement by this parasite to evade the lytic action of complement.

ACS Style

Alexandra Ibáñez-Escribano; Juan José Nogal-Ruiz; Jorge Pérez Serrano; Alicia Gómez-Barrio; J. Antonio Escario; J.F. Alderete. Sequestration of host-CD59 as potential immune evasion strategy of Trichomonas vaginalis. Acta Tropica 2015, 149, 1 -7.

AMA Style

Alexandra Ibáñez-Escribano, Juan José Nogal-Ruiz, Jorge Pérez Serrano, Alicia Gómez-Barrio, J. Antonio Escario, J.F. Alderete. Sequestration of host-CD59 as potential immune evasion strategy of Trichomonas vaginalis. Acta Tropica. 2015; 149 ():1-7.

Chicago/Turabian Style

Alexandra Ibáñez-Escribano; Juan José Nogal-Ruiz; Jorge Pérez Serrano; Alicia Gómez-Barrio; J. Antonio Escario; J.F. Alderete. 2015. "Sequestration of host-CD59 as potential immune evasion strategy of Trichomonas vaginalis." Acta Tropica 149, no. : 1-7.

Journal article
Published: 01 October 2014 in Journal of Microbiological Methods
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In the current report, a sequential step-wise methodology based on in silico, in vitro and in vivo experimental procedures for the prompt detection of potential trichomonacidal drugs is proposed. A combinatorial of 12 QSAR (Quantitative Structure-Activity Relationship) models based on Linear Discrimination Analysis (LDA) are suggested for the rational identification of new trichomonacidal drugs from virtual screening of in house chemical libraries and drug databases. Subsequently, compounds selected as potential anti-trichomonas are screened in vitro against Trichomonas vaginalis. Finally, molecules with specific trichomonacidal activity are evaluated in vivo. Herein, different molecules were exposed to the proposed methodology. Firstly, the agents were virtually screened and two of the eight molecules (G-1 and dimetridazole) were classified as trichomonacidals by the 12 models. Subsequently both drugs were proved in vitro and in vivo following the workflow procedure. Although a remarkable in vitro activity was observed in both cases, dimetridazole achieved higher MIC100 activity than metronidazole against the resistant isolate. Furthermore, the in vivo models showed a remarkable reduction of lesions of more than 55% in both compounds. These observations support the current flowchart screening and suggest the use of dimetridazole as a promising drug-like scaffold for novel therapeutic alternatives against T. vaginalis resistant infections.Peer Reviewe

ACS Style

Alexandra Ibáñez-Escribano; Alfredo Meneses-Marcel; Yovani Marrero-Ponce; Juan José Nogal-Ruiz; Vicente J. Arán; Alicia Gómez-Barrio; José Antonio Escario. A sequential procedure for rapid and accurate identification of putative trichomonacidal agents. Journal of Microbiological Methods 2014, 105, 162 -167.

AMA Style

Alexandra Ibáñez-Escribano, Alfredo Meneses-Marcel, Yovani Marrero-Ponce, Juan José Nogal-Ruiz, Vicente J. Arán, Alicia Gómez-Barrio, José Antonio Escario. A sequential procedure for rapid and accurate identification of putative trichomonacidal agents. Journal of Microbiological Methods. 2014; 105 ():162-167.

Chicago/Turabian Style

Alexandra Ibáñez-Escribano; Alfredo Meneses-Marcel; Yovani Marrero-Ponce; Juan José Nogal-Ruiz; Vicente J. Arán; Alicia Gómez-Barrio; José Antonio Escario. 2014. "A sequential procedure for rapid and accurate identification of putative trichomonacidal agents." Journal of Microbiological Methods 105, no. : 162-167.

Journal article
Published: 01 April 2014 in Parasitology International
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The nucleotide sequence of the 5.8S rRNA gene and the flanked internal transcribed spacer (ITS) regions of six Trichomonas vaginalis isolates with different metronidazole sensitivity and geographic origin were genotyped. A multiple sequence alignment was performed with different sequences of other isolates available at the GenBank/EMBL/DDBJ databases, which revealed 5 different sequence patterns. Although a stable mutation in position 66 of the ITS1 (C66T) was observed in 26% (9/34) of the T. vaginalis sequences analyzed, there was 99.7% ITS nucleotide sequence identity among isolates for this sequence. The nucleotide sequence variation among other species of the genus Trichomonas ranged from 3.4% to 9.1%. Surprisingly, the % identity between T. vaginalis and Pentatrichomonas hominis was ~. 83%. There was >. 40% divergence in the ITS sequence between T. vaginalis and Tritrichomonas spp., including Tritrichomonas augusta, Tritrichomonas muris, and Tritrichomonas nonconforma and with Tetratrichomonas prowazeki. Dendrograms grouped the trichomonadid sequences in robust clades according to their genera. The absence of nucleotide divergence in the hypervariable ITS regions between T. vaginalis isolates suggests the early divergence of the parasite. Importantly, these data show this ITS1-5.8S rRNA-ITS2 region suitable for inter-species differentiation. © 2014 Elsevier B.V.Peer Reviewe

ACS Style

Alexandra Ibáñez-Escribano; Juan José Nogal-Ruiz; Vicente J. Arán; José Antonio Escario; Alicia Gómez-Barrio; J.F. Alderete. Determination of internal transcribed spacer regions (ITS) in Trichomonas vaginalis isolates and differentiation among Trichomonas species. Parasitology International 2014, 63, 427 -431.

AMA Style

Alexandra Ibáñez-Escribano, Juan José Nogal-Ruiz, Vicente J. Arán, José Antonio Escario, Alicia Gómez-Barrio, J.F. Alderete. Determination of internal transcribed spacer regions (ITS) in Trichomonas vaginalis isolates and differentiation among Trichomonas species. Parasitology International. 2014; 63 (2):427-431.

Chicago/Turabian Style

Alexandra Ibáñez-Escribano; Juan José Nogal-Ruiz; Vicente J. Arán; José Antonio Escario; Alicia Gómez-Barrio; J.F. Alderete. 2014. "Determination of internal transcribed spacer regions (ITS) in Trichomonas vaginalis isolates and differentiation among Trichomonas species." Parasitology International 63, no. 2: 427-431.