A novel anti-inflammatory oligopeptide produced by Entamoeba histolytica

Kretschmer, R; Rico, Guadalupe; Giménez, Juliana

doi:10.1016/s0166-6851(00)00367-4

Cited by 30 publications

(35 citation statements)

References 21 publications

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“…All of the induced, in vitro, NO production models used in this study were significantly (P £ 0.05) and comparably inhibited by either nMLIF or sMLIF, except TNF-a stimulated U937 cells exposed to nMLIF. This confirmed the functional equivalence of the native and the synthetic MLIF material (Kretschmer et al 2001). The NO production induced by rhIFN-c was more vigorously ($50%) (P<0.005) inhibited by MLIF in PBMP than the relatively weaker NO production induced by TNF-a ($30% inhibition).…”

Section: Resultssupporting

confidence: 68%

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The monocyte locomotion inhibitory factor produced by Entamoeba histolytica inhibits induced nitric oxide production in human leukocytes

et al. 2003

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The monocyte locomotion inhibitory factor, an anti-inflammatory pentapeptide produced by Entamoeba histolytica, inhibits the in vitro production of nitric oxide induced by cytokines (INF-gamma, TNF-alpha) or PMA in human leukocytes. This can be added to the other previously reported functional effects of this factor, such as the inhibition of monocyte locomotion and the synthesis of reactive oxygen intermediates in both monocytes and neutrophils. The decreased nitric oxide production may interfere with the killing of amebas by neutrophils in the early invasive stages of amebiasis, when oxidative mechanisms are used [reactive oxygen and nitrogen intermediates either individually or synergistically via peroxynitrite (ONOO(-))], and in the advanced stages, when both non-oxidative and oxidative (including nitric oxide) mechanisms are employed by macrophages. Diminished nitric oxide production by leukocytes may also contribute to the paucity of late inflammatory components in amebic abscess of the liver and other amebic lesions.

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Section: Resultssupporting

confidence: 68%

“…The primary structure of MLIF was recently established [Met-Gln-Cys-Asn-Ser (MW=581 Da)]. A MLIF construct exhibits the same anti-inflammatory effects as the native material, while a scrambled version (GlnCys-Met-Ser-Asn) fails to do so (Kretschmer et al 2001).…”

Section: Introductionmentioning

confidence: 99%

The monocyte locomotion inhibitory factor produced by Entamoeba histolytica inhibits induced nitric oxide production in human leukocytes

et al. 2003

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“…Thus, Kretschmer and co-workers investigated anti-inflammatory factor production by means of the parasite Entamoeba histolytica that is the most prevalent intestinal protozoan pathogen worldwide [8], which produces a thermostable pentapeptide (Met-Gln-Cys-Asn-Ser) that in vitro inhibits mononuclear phagocyte locomotion; the original name assigned is human monocyte locomotion inhibitory factor (MLIF). These authors established that the same synthetic sequence possesses similar anti-inflammatory properties to those of native MLIF [9], whereas another analogous pentapeptide, that is, the proline amino acid, which was substituted with glutamine in the second position (Met-Pro-Cys-Asn-Ser, pMLIF), presented anti-inflammatory activity; however, another pentapeptide with the same amino acids but a different arrangement (Gln-Cys-Met-SerAsn, sMLIF) did not present anti-inflammatory activity. In early works, we have described the electronic structure and the physicochemical properties of the pentapeptides [10].…”

mentioning

confidence: 94%

The influence of electron donor and electron acceptor groups on the electronic structure of the anti‐inflammatory tripeptide Cys‐Asn‐Ser

Soriano-Correa

Barrientos-Salcedo

Raya

et al. 2010

Int J of Quantum Chemistry

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It has been discussed in the literature that electron delocalization along the peptide backbone and side chain modulates the physical and chemical features of peptides and proteins. The structure and properties of peptides are determined by their charge-density distribution, such that the modification of its side chain plays an important role on its electronic structure and physicochemical properties. Research on Entamoeba histolytica soluble factors led to the identification of the pentapeptide Met-Gln-Cys-Asn-Ser, with anti-inflammatory in vivo and in vitro effects. A synthetic pentapeptide, Met-Pro-Cys-Asn-Ser, maintained the same anti-inflammatory actions in experimental assays. A previous theoretical study allowed proposing the Cys-Asn-Ser tripeptide (CNS tripeptide) as the pharmacophore group of both molecules. This theoretical hypothesis was recently confirmed experimentally. The objective of this work was to study the influence of the electron donor and electron withdrawing substituent groups on the electronic structure and physicochemical properties of the CNS tripeptide derivatives through a theoretical study at the density functional theory level of theory. Our results in deprotonation energies showed that the relative acidity of hydrogen atom (H2) of the serine-amide group increases with the electron withdrawing groups. This result was confirmed by means of a study of bond order. The proton affinities illustrated that the electron donor groups favored the basicity of the amino group of the cysteine amino acid. Atomic charges, Frontier molecular orbitals (HOMO-LUMO), and electrostatic potential isosurface and its geometric parameters permitted to analyze the effect that provoked the electron donor and electron attractor groups on its electronic structure and physicochemical features and to identify some reactive sites that could be associated with the anti-inflammatory activity of tripeptide CNS derivatives.

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“…This peak was rechromatographed and concentrated in preparation for mass spectrophotometry and, finally, sequencing by the Edman method. Edman N-degradation-sequencing confirmed the primary chemical structure of MLIF: Met-Gln-Cys-Asn-Ser (molecular mass = 581 Da) [24]. A synthetic construct displays the same effects as the native material [24].…”

Section: Monocyte Locomotion Inhibitory Factormentioning

confidence: 74%

Anti-inflammatory defense mechanisms of Entamoeba histolytica

Silva-García

Rico-Rosillo²

2010

Inflamm. Res.

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The monocyte locomotion inhibitory factor (MLIF), a heat-stable oligopeptide found in the supernatant fluid of Entamoeba histolytica axenic cultures, may contribute to the delayed inflammation observed in amoebic hepatic abscess. This factor was isolated by ultra-filtration and high powered liquid chromatography, obtaining a primary Met-Gln-Cys-Asn-Ser structure, identified afterwards as the carboxyl-terminal (…Cys-Asn-Ser) active site. The selective anti-inflammatory effects of the pentapeptide have been observed in both in vitro and in vivo models, using a synthetic pentapeptide to maintain the same anti-inflammatory conditions during the experimental assays. Anti-inflammatory effects observed include inhibition of human monocyte locomotion and the respiratory burst in monocytes and neutrophils, increasing expression of anti-inflammatory cytokines and inhibiting expression of the adhesion molecules VLA-4 and VCAM, among others. In this review, we will describe the effects of MLIF detected so far and how it might be used as a therapeutical agent against inflammatory diseases.

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A novel anti-inflammatory oligopeptide produced by Entamoeba histolytica

Cited by 30 publications

References 21 publications

The monocyte locomotion inhibitory factor produced by Entamoeba histolytica inhibits induced nitric oxide production in human leukocytes

The monocyte locomotion inhibitory factor produced by Entamoeba histolytica inhibits induced nitric oxide production in human leukocytes

The influence of electron donor and electron acceptor groups on the electronic structure of the anti‐inflammatory tripeptide Cys‐Asn‐Ser

Anti-inflammatory defense mechanisms of Entamoeba histolytica

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