Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity

A series of novel xylitan derivatives derived from xylitol were synthesized using operationally simple procedures. A xylitan acetonide was the key intermediate used to prepare benzoate, arylsulfonate esters and 1,2,3-triazole derivatives of xylitan. These compounds were evaluated for their in vitro...

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Main Authors:	Paula Regina Elias, Gleicekelly Silva Coelho, Viviane Flores Xavier, Policarpo Ademar Sales Junior, Alvaro José Romanha, Silvane Maria Fonseca Murta, Claudia Martins Carneiro, Nilton Soares Camilo, Flaviane Francisco Hilário, Jason Guy Taylor
Format:	Article
Language:	English
Published:	MDPI AG 2016-10-01
Series:	Molecules
Subjects:	xylitan xylitol anhydropentitol amastigote trypomastigote in vitro chagas disease
Online Access:	http://www.mdpi.com/1420-3049/21/10/1342

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spelling	doaj-f3c4f9968b334497ab80a6da4c5440bf2020-11-24T20:58:47ZengMDPI AGMolecules1420-30492016-10-012110134210.3390/molecules21101342molecules21101342Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal ActivityPaula Regina Elias0Gleicekelly Silva Coelho1Viviane Flores Xavier2Policarpo Ademar Sales Junior3Alvaro José Romanha4Silvane Maria Fonseca Murta5Claudia Martins Carneiro6Nilton Soares Camilo7Flaviane Francisco Hilário8Jason Guy Taylor9Chemistry Department, ICEB, Federal University of Ouro Preto, Campus Universitário Morro do Cruzeiro, 35400-000 Ouro Preto, MG, BrazilChemistry Department, ICEB, Federal University of Ouro Preto, Campus Universitário Morro do Cruzeiro, 35400-000 Ouro Preto, MG, BrazilChemistry Department, ICEB, Federal University of Ouro Preto, Campus Universitário Morro do Cruzeiro, 35400-000 Ouro Preto, MG, BrazilCentro de Pesquisas René Rachou, A Fundação Oswaldo Cruz/FIOCRUZ, 30190-002 Belo Horizonte, MG, BrazilCentro de Pesquisas René Rachou, A Fundação Oswaldo Cruz/FIOCRUZ, 30190-002 Belo Horizonte, MG, BrazilCentro de Pesquisas René Rachou, A Fundação Oswaldo Cruz/FIOCRUZ, 30190-002 Belo Horizonte, MG, BrazilImmunopathology Laboratory, NUPEB, Federal University of Ouro Preto, Campus Universitário Morro do Cruzeiro, 35400-000 Ouro Preto-MG, BrazilInstituto de Química, Universidade Estadual de Campinas, C.P. 6154, CEP. 13084-971 Campinas, SP, BrazilChemistry Department, ICEB, Federal University of Ouro Preto, Campus Universitário Morro do Cruzeiro, 35400-000 Ouro Preto, MG, BrazilChemistry Department, ICEB, Federal University of Ouro Preto, Campus Universitário Morro do Cruzeiro, 35400-000 Ouro Preto, MG, BrazilA series of novel xylitan derivatives derived from xylitol were synthesized using operationally simple procedures. A xylitan acetonide was the key intermediate used to prepare benzoate, arylsulfonate esters and 1,2,3-triazole derivatives of xylitan. These compounds were evaluated for their in vitro anti-Trypanosoma cruzi activity against trypomastigote and amastigote forms of the parasite in T. cruzi-infected cell lineages. Benznidazole was used as positive control against T. cruzi and cytotoxicity was determined in mammalian L929 cells. The arylsulfonate xylitan derivative bearing a nitro group displayed the best activity of all the compounds tested, and was slightly more potent than the reference drug benznidazole. The importance of the isopropylidene ketal moiety was established and the greater lipophilicity of these compounds suggests enhancement in cell penetration.http://www.mdpi.com/1420-3049/21/10/1342xylitanxylitolanhydropentitolamastigotetrypomastigotein vitrochagas disease
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Paula Regina Elias Gleicekelly Silva Coelho Viviane Flores Xavier Policarpo Ademar Sales Junior Alvaro José Romanha Silvane Maria Fonseca Murta Claudia Martins Carneiro Nilton Soares Camilo Flaviane Francisco Hilário Jason Guy Taylor
spellingShingle	Paula Regina Elias Gleicekelly Silva Coelho Viviane Flores Xavier Policarpo Ademar Sales Junior Alvaro José Romanha Silvane Maria Fonseca Murta Claudia Martins Carneiro Nilton Soares Camilo Flaviane Francisco Hilário Jason Guy Taylor Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity Molecules xylitan xylitol anhydropentitol amastigote trypomastigote in vitro chagas disease
author_facet	Paula Regina Elias Gleicekelly Silva Coelho Viviane Flores Xavier Policarpo Ademar Sales Junior Alvaro José Romanha Silvane Maria Fonseca Murta Claudia Martins Carneiro Nilton Soares Camilo Flaviane Francisco Hilário Jason Guy Taylor
author_sort	Paula Regina Elias
title	Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity
title_short	Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity
title_full	Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity
title_fullStr	Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity
title_full_unstemmed	Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity
title_sort	synthesis of xylitan derivatives and preliminary evaluation of in vitro trypanocidal activity
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2016-10-01
description	A series of novel xylitan derivatives derived from xylitol were synthesized using operationally simple procedures. A xylitan acetonide was the key intermediate used to prepare benzoate, arylsulfonate esters and 1,2,3-triazole derivatives of xylitan. These compounds were evaluated for their in vitro anti-Trypanosoma cruzi activity against trypomastigote and amastigote forms of the parasite in T. cruzi-infected cell lineages. Benznidazole was used as positive control against T. cruzi and cytotoxicity was determined in mammalian L929 cells. The arylsulfonate xylitan derivative bearing a nitro group displayed the best activity of all the compounds tested, and was slightly more potent than the reference drug benznidazole. The importance of the isopropylidene ketal moiety was established and the greater lipophilicity of these compounds suggests enhancement in cell penetration.
topic	xylitan xylitol anhydropentitol amastigote trypomastigote in vitro chagas disease
url	http://www.mdpi.com/1420-3049/21/10/1342
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Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity

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