Synthesis of PEGylated lactose analogs for inhibition studies on T.cruzi trans-sialidase
Trypanosoma cruzi, the agent of Chagas disease, expresses a unique enzyme, the trans-sialidase (TcTS) involved in the transfer of sialic acid from host glycoconjugates to mucins of the parasite. The enzyme is shed to the medium and may affect the immune system of the host. We have previously describ...
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2010
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paper:paper_02820080_v27_n5_p549_Giorgi2023-06-08T15:26:59Z Synthesis of PEGylated lactose analogs for inhibition studies on T.cruzi trans-sialidase Giorgi, María Eugenia Ratier, Laura Agustí, Rosalía Muchnik de Lederkremer, Rosa María Inhibitors PEGylation Trans-sialidase Trypanosoma cruzi benzyl beta dextro galactopyranosyl (1-6) 2 amino 2 deoxy alpha dextro glucopyranoside glucopyranoside lactobionolactone lactose lactose derivative macrogol sialidase inhibitor unclassified drug animal experiment article chemical modification concentration response controlled study drug bioavailability drug conjugation drug stability drug synthesis enzyme inhibition enzyme mechanism mouse nonhuman priority journal Trypanosoma cruzi Trypanosoma cruzi Trypanosoma cruzi, the agent of Chagas disease, expresses a unique enzyme, the trans-sialidase (TcTS) involved in the transfer of sialic acid from host glycoconjugates to mucins of the parasite. The enzyme is shed to the medium and may affect the immune system of the host. We have previously described that lactose derivatives effectively inhibited the transfer of sialic acid to N-acetyllactosamine. Lactitol also prevented the apoptosis caused by the TcTS, although it is rapidly eliminated from the circulatory system. In this paper we report covalent conjugation of polyethylene glycol (PEG) with lactose, lactobionolactone and benzyl β-D-galactopyranosyl-(1→6)-2-amino-2- deoxy-α-D-glucopyranoside (1) with the hope to improve the bioavailability, though retaining their inhibitory properties. Different conjugation methods have been used and the behavior of the PEGylated products in the TcTS reaction was studied. © 2010 Springer Science+Business Media, LLC. Fil:Giorgi, M.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ratier, L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Agusti, R. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:De Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2010 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02820080_v27_n5_p549_Giorgi http://hdl.handle.net/20.500.12110/paper_02820080_v27_n5_p549_Giorgi |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Inhibitors PEGylation Trans-sialidase Trypanosoma cruzi benzyl beta dextro galactopyranosyl (1-6) 2 amino 2 deoxy alpha dextro glucopyranoside glucopyranoside lactobionolactone lactose lactose derivative macrogol sialidase inhibitor unclassified drug animal experiment article chemical modification concentration response controlled study drug bioavailability drug conjugation drug stability drug synthesis enzyme inhibition enzyme mechanism mouse nonhuman priority journal Trypanosoma cruzi Trypanosoma cruzi |
| spellingShingle |
Inhibitors PEGylation Trans-sialidase Trypanosoma cruzi benzyl beta dextro galactopyranosyl (1-6) 2 amino 2 deoxy alpha dextro glucopyranoside glucopyranoside lactobionolactone lactose lactose derivative macrogol sialidase inhibitor unclassified drug animal experiment article chemical modification concentration response controlled study drug bioavailability drug conjugation drug stability drug synthesis enzyme inhibition enzyme mechanism mouse nonhuman priority journal Trypanosoma cruzi Trypanosoma cruzi Giorgi, María Eugenia Ratier, Laura Agustí, Rosalía Muchnik de Lederkremer, Rosa María Synthesis of PEGylated lactose analogs for inhibition studies on T.cruzi trans-sialidase |
| topic_facet |
Inhibitors PEGylation Trans-sialidase Trypanosoma cruzi benzyl beta dextro galactopyranosyl (1-6) 2 amino 2 deoxy alpha dextro glucopyranoside glucopyranoside lactobionolactone lactose lactose derivative macrogol sialidase inhibitor unclassified drug animal experiment article chemical modification concentration response controlled study drug bioavailability drug conjugation drug stability drug synthesis enzyme inhibition enzyme mechanism mouse nonhuman priority journal Trypanosoma cruzi Trypanosoma cruzi |
| description |
Trypanosoma cruzi, the agent of Chagas disease, expresses a unique enzyme, the trans-sialidase (TcTS) involved in the transfer of sialic acid from host glycoconjugates to mucins of the parasite. The enzyme is shed to the medium and may affect the immune system of the host. We have previously described that lactose derivatives effectively inhibited the transfer of sialic acid to N-acetyllactosamine. Lactitol also prevented the apoptosis caused by the TcTS, although it is rapidly eliminated from the circulatory system. In this paper we report covalent conjugation of polyethylene glycol (PEG) with lactose, lactobionolactone and benzyl β-D-galactopyranosyl-(1→6)-2-amino-2- deoxy-α-D-glucopyranoside (1) with the hope to improve the bioavailability, though retaining their inhibitory properties. Different conjugation methods have been used and the behavior of the PEGylated products in the TcTS reaction was studied. © 2010 Springer Science+Business Media, LLC. |
| author |
Giorgi, María Eugenia Ratier, Laura Agustí, Rosalía Muchnik de Lederkremer, Rosa María |
| author_facet |
Giorgi, María Eugenia Ratier, Laura Agustí, Rosalía Muchnik de Lederkremer, Rosa María |
| author_sort |
Giorgi, María Eugenia |
| title |
Synthesis of PEGylated lactose analogs for inhibition studies on T.cruzi trans-sialidase |
| title_short |
Synthesis of PEGylated lactose analogs for inhibition studies on T.cruzi trans-sialidase |
| title_full |
Synthesis of PEGylated lactose analogs for inhibition studies on T.cruzi trans-sialidase |
| title_fullStr |
Synthesis of PEGylated lactose analogs for inhibition studies on T.cruzi trans-sialidase |
| title_full_unstemmed |
Synthesis of PEGylated lactose analogs for inhibition studies on T.cruzi trans-sialidase |
| title_sort |
synthesis of pegylated lactose analogs for inhibition studies on t.cruzi trans-sialidase |
| publishDate |
2010 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02820080_v27_n5_p549_Giorgi http://hdl.handle.net/20.500.12110/paper_02820080_v27_n5_p549_Giorgi |
| work_keys_str_mv |
AT giorgimariaeugenia synthesisofpegylatedlactoseanalogsforinhibitionstudiesontcruzitranssialidase AT ratierlaura synthesisofpegylatedlactoseanalogsforinhibitionstudiesontcruzitranssialidase AT agustirosalia synthesisofpegylatedlactoseanalogsforinhibitionstudiesontcruzitranssialidase AT muchnikdelederkremerrosamaria synthesisofpegylatedlactoseanalogsforinhibitionstudiesontcruzitranssialidase |
| _version_ |
1768545973329461248 |