Why lamivudine assembles into double-stranded helices in crystals: Salt heterosynthon: Versus base-pairing homosynthon

Autores
Chapeletti da Silva, Cameron; Medanha Valdo, Ana K.; do Nascimento Neto, José Antonio; Ribeiro, Leandro Agustín; Sarotti, Ariel Marcelo; Martins Terra, Felipe
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Here we were interested in obtaining a better understanding of the competition between the salt heterosynthon and the base-pairing homosynthon formed by the anti-HIV drug lamivudine in the presence of strong acids. Even though the preparation of the multicomponent crystal forms of this drug with weak or moderate acids is well investigated, the crystallization of lamivudine with strong acids is still little explored. Besides filling this crystallization screening gap, the driving forces of the so-called lamivudine duplexes could be drawn from the complete structural landscape and the theoretical thermodynamic parameters of the salt heterosynthon, calculated at the M06-2X/6-31+G∗∗ level of theory. Five new crystal structures of lamivudine were obtained, wherein two of them were assembled as base-paired helically-stacked strands in the presence of trifluoroacetic and trichloroacetic acids (lamivudine duplexes V and VI, respectively). Besides, three salts were prepared by crystallization of lamivudine with sulfuric and perchloric acids. Finally, the theoretical approach showed that there is no energy trend regarding the formation of lamivudine duplexes with aliphatic organic acids or lamivudine salts with aromatic acids, which is usually observed in practice.
Fil: Chapeletti da Silva, Cameron. Universidade Federal de Goiás; Brasil
Fil: Medanha Valdo, Ana K.. Universidade Federal de Goiás; Brasil
Fil: do Nascimento Neto, José Antonio. Universidade Federal de Goiás; Brasil
Fil: Ribeiro, Leandro Agustín. Universidade Federal de Goiás; Brasil
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Martins Terra, Felipe. Universidade Federal de Goiás; Brasil
Materia
LAMIVUDINE
HELICES
CRYSTALS
DFT
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/87147
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/87147
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Why lamivudine assembles into double-stranded helices in crystals: Salt heterosynthon: Versus base-pairing homosynthonChapeletti da Silva, CameronMedanha Valdo, Ana K.do Nascimento Neto, José AntonioRibeiro, Leandro AgustínSarotti, Ariel MarceloMartins Terra, FelipeLAMIVUDINEHELICESCRYSTALSDFThttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Here we were interested in obtaining a better understanding of the competition between the salt heterosynthon and the base-pairing homosynthon formed by the anti-HIV drug lamivudine in the presence of strong acids. Even though the preparation of the multicomponent crystal forms of this drug with weak or moderate acids is well investigated, the crystallization of lamivudine with strong acids is still little explored. Besides filling this crystallization screening gap, the driving forces of the so-called lamivudine duplexes could be drawn from the complete structural landscape and the theoretical thermodynamic parameters of the salt heterosynthon, calculated at the M06-2X/6-31+G∗∗ level of theory. Five new crystal structures of lamivudine were obtained, wherein two of them were assembled as base-paired helically-stacked strands in the presence of trifluoroacetic and trichloroacetic acids (lamivudine duplexes V and VI, respectively). Besides, three salts were prepared by crystallization of lamivudine with sulfuric and perchloric acids. Finally, the theoretical approach showed that there is no energy trend regarding the formation of lamivudine duplexes with aliphatic organic acids or lamivudine salts with aromatic acids, which is usually observed in practice.Fil: Chapeletti da Silva, Cameron. Universidade Federal de Goiás; BrasilFil: Medanha Valdo, Ana K.. Universidade Federal de Goiás; BrasilFil: do Nascimento Neto, José Antonio. Universidade Federal de Goiás; BrasilFil: Ribeiro, Leandro Agustín. Universidade Federal de Goiás; BrasilFil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Martins Terra, Felipe. Universidade Federal de Goiás; BrasilRoyal Society of Chemistry2018-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/87147Chapeletti da Silva, Cameron; Medanha Valdo, Ana K.; do Nascimento Neto, José Antonio; Ribeiro, Leandro Agustín; Sarotti, Ariel Marcelo; et al.; Why lamivudine assembles into double-stranded helices in crystals: Salt heterosynthon: Versus base-pairing homosynthon; Royal Society of Chemistry; CrystEngComm; 20; 22; 9-2018; 3049-30571466-8033CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/c8ce00100finfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2018/CE/C8CE00100F#!divAbstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:50:50Zoai:ri.conicet.gov.ar:11336/87147instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:50:51.082CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Why lamivudine assembles into double-stranded helices in crystals: Salt heterosynthon: Versus base-pairing homosynthon
title Why lamivudine assembles into double-stranded helices in crystals: Salt heterosynthon: Versus base-pairing homosynthon
spellingShingle Why lamivudine assembles into double-stranded helices in crystals: Salt heterosynthon: Versus base-pairing homosynthon
Chapeletti da Silva, Cameron
LAMIVUDINE
HELICES
CRYSTALS
DFT
title_short Why lamivudine assembles into double-stranded helices in crystals: Salt heterosynthon: Versus base-pairing homosynthon
title_full Why lamivudine assembles into double-stranded helices in crystals: Salt heterosynthon: Versus base-pairing homosynthon
title_fullStr Why lamivudine assembles into double-stranded helices in crystals: Salt heterosynthon: Versus base-pairing homosynthon
title_full_unstemmed Why lamivudine assembles into double-stranded helices in crystals: Salt heterosynthon: Versus base-pairing homosynthon
title_sort Why lamivudine assembles into double-stranded helices in crystals: Salt heterosynthon: Versus base-pairing homosynthon
dc.creator.none.fl_str_mv Chapeletti da Silva, Cameron
Medanha Valdo, Ana K.
do Nascimento Neto, José Antonio
Ribeiro, Leandro Agustín
Sarotti, Ariel Marcelo
Martins Terra, Felipe
author Chapeletti da Silva, Cameron
author_facet Chapeletti da Silva, Cameron
Medanha Valdo, Ana K.
do Nascimento Neto, José Antonio
Ribeiro, Leandro Agustín
Sarotti, Ariel Marcelo
Martins Terra, Felipe
author_role author
author2 Medanha Valdo, Ana K.
do Nascimento Neto, José Antonio
Ribeiro, Leandro Agustín
Sarotti, Ariel Marcelo
Martins Terra, Felipe
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv LAMIVUDINE
HELICES
CRYSTALS
DFT
topic LAMIVUDINE
HELICES
CRYSTALS
DFT
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Here we were interested in obtaining a better understanding of the competition between the salt heterosynthon and the base-pairing homosynthon formed by the anti-HIV drug lamivudine in the presence of strong acids. Even though the preparation of the multicomponent crystal forms of this drug with weak or moderate acids is well investigated, the crystallization of lamivudine with strong acids is still little explored. Besides filling this crystallization screening gap, the driving forces of the so-called lamivudine duplexes could be drawn from the complete structural landscape and the theoretical thermodynamic parameters of the salt heterosynthon, calculated at the M06-2X/6-31+G∗∗ level of theory. Five new crystal structures of lamivudine were obtained, wherein two of them were assembled as base-paired helically-stacked strands in the presence of trifluoroacetic and trichloroacetic acids (lamivudine duplexes V and VI, respectively). Besides, three salts were prepared by crystallization of lamivudine with sulfuric and perchloric acids. Finally, the theoretical approach showed that there is no energy trend regarding the formation of lamivudine duplexes with aliphatic organic acids or lamivudine salts with aromatic acids, which is usually observed in practice.
Fil: Chapeletti da Silva, Cameron. Universidade Federal de Goiás; Brasil
Fil: Medanha Valdo, Ana K.. Universidade Federal de Goiás; Brasil
Fil: do Nascimento Neto, José Antonio. Universidade Federal de Goiás; Brasil
Fil: Ribeiro, Leandro Agustín. Universidade Federal de Goiás; Brasil
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Martins Terra, Felipe. Universidade Federal de Goiás; Brasil
description Here we were interested in obtaining a better understanding of the competition between the salt heterosynthon and the base-pairing homosynthon formed by the anti-HIV drug lamivudine in the presence of strong acids. Even though the preparation of the multicomponent crystal forms of this drug with weak or moderate acids is well investigated, the crystallization of lamivudine with strong acids is still little explored. Besides filling this crystallization screening gap, the driving forces of the so-called lamivudine duplexes could be drawn from the complete structural landscape and the theoretical thermodynamic parameters of the salt heterosynthon, calculated at the M06-2X/6-31+G∗∗ level of theory. Five new crystal structures of lamivudine were obtained, wherein two of them were assembled as base-paired helically-stacked strands in the presence of trifluoroacetic and trichloroacetic acids (lamivudine duplexes V and VI, respectively). Besides, three salts were prepared by crystallization of lamivudine with sulfuric and perchloric acids. Finally, the theoretical approach showed that there is no energy trend regarding the formation of lamivudine duplexes with aliphatic organic acids or lamivudine salts with aromatic acids, which is usually observed in practice.
publishDate 2018
dc.date.none.fl_str_mv 2018-09
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/87147
Chapeletti da Silva, Cameron; Medanha Valdo, Ana K.; do Nascimento Neto, José Antonio; Ribeiro, Leandro Agustín; Sarotti, Ariel Marcelo; et al.; Why lamivudine assembles into double-stranded helices in crystals: Salt heterosynthon: Versus base-pairing homosynthon; Royal Society of Chemistry; CrystEngComm; 20; 22; 9-2018; 3049-3057
1466-8033
CONICET Digital
CONICET
url http://hdl.handle.net/11336/87147
identifier_str_mv Chapeletti da Silva, Cameron; Medanha Valdo, Ana K.; do Nascimento Neto, José Antonio; Ribeiro, Leandro Agustín; Sarotti, Ariel Marcelo; et al.; Why lamivudine assembles into double-stranded helices in crystals: Salt heterosynthon: Versus base-pairing homosynthon; Royal Society of Chemistry; CrystEngComm; 20; 22; 9-2018; 3049-3057
1466-8033
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/c8ce00100f
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2018/CE/C8CE00100F#!divAbstract
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.13397

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