Fragments of the second transmembrane helix of three G-protein-coupled receptors: comparative synthetic, structural and conformational studies

Lopes, Douglas Duarte; Cuvero, Jamille H; Ferreira, Mariana Mendonça; Silva, Rogério L; Souza, Sinval E. G.; Malavolta, Luciana; Schreier, Shirley; Nakaie, Clóvis R.

doi:10.1007/s00726-018-2662-z

Cited by 4 publications

(7 citation statements)

References 46 publications

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“…Noteworthy and in accordance with these resin swelling data, there was no need for a Gln⟶Asn recoupling reaction in BUBHAR as systematically occurred with MBHAR. This result strongly supports the importance of the resin solvation property as previously demonstrated in critical acylation reactions within beads in other peptideresins [23][24][25].…”

Section: Solvation Studies Of Asn-cys-pro-(d-arg)-gly-resinssupporting

confidence: 89%

“…In order to complement the above-described peptide-resin solvation, the degree of motion and steric hindrance neighboring of the peptide chains spread throughout the resin beads were now estimated by EPR experiments. Small portion of the N-terminal groups of peptide chains in both resins were labeled with the amino acid-type spin probe Toac (2,2,6,6tetramethylpiperidine-N-oxyl-4-amino-4-carboxylic acid) introduced by us for peptide and polymer labeling [26][27][28] as previously described for evaluating, for instance, the solvation properties of model peptide-polymers [21][22][23][24][25].…”

Section: Solvation Studies Of Asn-cys-pro-(d-arg)-gly-resinsmentioning

confidence: 99%

“…As a rule [16,25], there is an inverse correlation between the W 0 value and the rate of labeled molecular motion. Comparatively smaller W 0 values were obtained for peptide-BUBHAR than for peptide-MBHAR in all solvent systems, which were in close agreement with the swelling data of both peptide-resins.…”

Section: Solvation Studies Of Asn-cys-pro-(d-arg)-gly-resinsmentioning

confidence: 99%

“…Figure2shows the EPR spectra of both peptide-resins in the solvent system (50% DCM: DMF) used for the coupling step of peptide synthesis in the present study, and Table2displays the EPR central peak line widths (W 0 ) values (in Gauss) that are known to be sensitive to the level of molecular mobility of labeled sites within resin network[16,22].As a rule[16,25], there is an inverse correlation between the W 0 value and the rate of labeled molecular motion. Comparatively smaller W 0 values were obtained for peptide-BUBHAR than for peptide-MBHAR in all solvent systems, which were in close agreement with the swelling data of both peptide-resins.Lastly, the analytical HPLC profiles of the crude Gln-Asn-Cys-Pro-(D-Arg)-Gly-peptide fragment assembled in both resins are shown in Figure3.…”

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confidence: 99%

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Evaluation of 4-tert-Butyl-Benzhydrylamine Resin (BUBHAR) as an Alternative Solid Support for Peptide Synthesis

Souza

Malavolta

Salomoni

et al. 2020

International Journal of Polymer Science

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Following preliminary reports that introduced 4-tert-butylbenzhydrylamine resin (BUBHAR) as a novel polymer for use in solid-phase peptide chemistry (SPPS), some physical-chemical properties of its structure, certainly relevant for its application in this methodology, were compared with those of the largely used methylbenzhydrylamine resin (MBHAR). In order to rule out possible MBHAR-related commercial source effects for SPPS, we initially compared MBHAR batches acquired from three different manufacturers with homemade BUBHARs. The bead solvation properties of these two resins in solvents used in the tert-butyl (Boc-based) SPPS technique indicated that the mean swelling values of these solid supports (% volume of solvated bead occupied by the solvent) were 51% and 67% for MBHAR and BUBHAR, respectively. This result strongly suggests a good potential for the latter polymer in terms of application for application in SPPS. In order to move forward with this approach, the synthesis of the carboxy-terminal peptide fragment (Gln-Asn-Cys-Pro-(D-Arg)-Gly-amide) of the antidiuretic hormone, desmopressin ([3-Mpa∗-Tyr-Phe-Gln-Asn-Cys-Pro-(D-Arg)-Gly-amide], ∗1-[3-mercaptopropionic acid]), which our laboratory is producing routinely in large scale for the Health Secretary of Sao Paulo State. The comparative synthesis was conducted using these two resins with similar substitution degrees (~0.7 mmol/g). In contrast to MBHAR, surprisingly no need for a Gln⟶Asn recoupling reaction was observed when BUBHAR was used. This result might be due to improved solvation of the desmopressin C-terminal Asn-Cys-Pro-(D-Arg)-Gly-segment when bound to this latter resin as observed by microscopic swelling degrees of peptide-resin beads and also by greater mobility detected of peptide chains within the BUBHAR polymer backbone. This finding was determined by comparative electron paramagnetic resonance (EPR) of both peptide resins attaching the amino acid-type paramagnetic 2.2.6.6-tetramethylpiperidine-1-oxyl-4-amino-4-carboxylic acid (Toac) spin label early introduced by our group.

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Section: Solvation Studies Of Asn-cys-pro-(d-arg)-gly-resinssupporting

confidence: 89%

Section: Solvation Studies Of Asn-cys-pro-(d-arg)-gly-resinsmentioning

confidence: 99%

Section: Solvation Studies Of Asn-cys-pro-(d-arg)-gly-resinsmentioning

confidence: 99%

mentioning

confidence: 99%

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Evaluation of 4-tert-Butyl-Benzhydrylamine Resin (BUBHAR) as an Alternative Solid Support for Peptide Synthesis

Souza

Malavolta

Salomoni

et al. 2020

International Journal of Polymer Science

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“…Angiotensin II was synthesized manually by the solid phase peptide synthesis methodology using the t ‐Boc(tert‐butyloxycarbonyl)‐strategy. The crude peptide was purified through Waters Delta 600 preparative high‐performance liquid chromatography (HPLC) equipment and the isolated sample was characterized by HPLC Waters Alliance analytical and electrospray ionization mass spectrometry (LC/ESI‐MS) experiments (Lopes et al, 2019). This peptide was kindly provided for this study by Prof. Dr. Clovis Ryuichi Nakaie, from the Department of Biophysics, EPM, Universidade Federal de São Paulo (UNIFESP).…”

Section: Methodsmentioning

confidence: 99%

Angiotensin II modulates the murine hematopoietic stem cell and progenitors cocultured with stromal S17 cells

Costa

Stilhano

Oliveira

et al. 2021

Cell Biology International

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Although the existence of the renin–angiotensin system (RAS) in the bone marrow is clear, the exact role of this system in hematopoiesis has not yet been fully characterized. Here the direct role of angiotensin II (AngII) in hematopoietic stem cells (HSCs), common myeloid progenitors (CMPs), granulocyte/monocyte progenitors (GMPs), and megakaryocytes/erythroid progenitors (MEPs), using a system of coculture with stromal S17 cells. Flow cytometry analysis showed that AngII increases the percentage of HSC and GMP, while reducing CMP with no effect on MEP. According to these data, AngII increased the total number of mature Gr‐1+/Mac‐1+ cells without changes in Terr119+ cells. AngII does not induce cell death in the population of LSK cells. In these populations, treatment with AngII decreases the expression of Ki67+ protein with no changes in the Notch1 expression, suggesting a role for AngII on the quiescence of immature cells. In addition, exposure to AngII from murine bone marrow cells increased the number of CFU‐GM and BFU‐E in a clonogenic assay. In conclusion, our data showed that AngII is involved in the regulation of hematopoiesis with a special role in HSC, suggesting that AngII should be evaluated in coculture systems, especially in cases that require the expansion of these cells in vitro, still a significant challenge for therapeutic applications in humans.

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Peptide inhibitors of angiotensin-I converting enzyme based on angiotensin (1–7) with selectivity for the C-terminal domain

Silva

Papakyriakou²,

Carmona³

et al. 2022

Bioorganic Chemistry

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Fragments of the second transmembrane helix of three G-protein-coupled receptors: comparative synthetic, structural and conformational studies

Cited by 4 publications

References 46 publications

Evaluation of 4-tert-Butyl-Benzhydrylamine Resin (BUBHAR) as an Alternative Solid Support for Peptide Synthesis

Evaluation of 4-tert-Butyl-Benzhydrylamine Resin (BUBHAR) as an Alternative Solid Support for Peptide Synthesis

Angiotensin II modulates the murine hematopoietic stem cell and progenitors cocultured with stromal S17 cells

Peptide inhibitors of angiotensin-I converting enzyme based on angiotensin (1–7) with selectivity for the C-terminal domain

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