Efficient catalytic oxidation of 3-arylthio- and 3-cyclohexylthio-lapachone derivatives to new sulfonyl derivatives and evaluation of their antibacterial activities

Mariana F.Do C. Cardoso; Ana T.P.C. Gomes; Caroline Dos S. Moreira; Mário M.Q. Simões; Maria G.P.M.S. Neves; David R. Da Rocha; Fernando De C. Da Silva; Catarina Moreirinha; Adelaide Almeida; Vitor F. Ferreira; José A.S. Cavaleiro; João Paulo C. Tomé

doi:10.3390/molecules22020302

Efficient catalytic oxidation of 3-arylthio- and 3-cyclohexylthio-lapachone derivatives to new sulfonyl derivatives and evaluation of their antibacterial activities

Mariana F.Do C. Cardoso
, Ana T.P.C. Gomes
, Caroline Dos S. Moreira
, Mário M.Q. Simões
, Maria G.P.M.S. Neves
, David R. Da Rocha
, Fernando De C. Da Silva
, Catarina Moreirinha
, Adelaide Almeida
, Vitor F. Ferreira
, José A.S. Cavaleiro^*
, João Paulo C. Tomé

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

New sulfonyl-lapachones were efficiently obtained through the catalytic oxidation of arylthio- and cyclohexylthio-lapachone derivatives with hydrogen peroxide in the presence of a Mn(III) porphyrin complex. The antibacterial activities of the non-oxidized and oxidized lapachone derivatives against the Gram-negative bacteria Escherichia coli and the Gram-positive bacteria Staphylococcus aureus were evaluated after their incorporation into polyvinylpyrrolidone (PVP) micelles. The obtained results show that the PVP-formulations of the lapachones 4b-g and of the sulfonyl-lapachones 7e and 7g reduced the growth of S. aureus.

Original language	English
Article number	302
Journal	Molecules
Volume	22
Issue number	2
DOIs	https://doi.org/10.3390/molecules22020302
Publication status	Published - Feb 2017
Externally published	Yes

Keywords

Antibacterial activity
Arylthio/cyclohexylthio-lapachones
Hydrogen peroxide
Oxidation
Polyvinylpyrrolidone
PorphyrinatoMn(III)
Sulfonyl-lapachones

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10.3390/molecules22020302Licence: CC BY

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Cardoso, M. F. D. C., Gomes, A. T. P. C., Moreira, C. D. S., Simões, M. M. Q., Neves, M. G. P. M. S., Da Rocha, D. R., Da Silva, F. D. C., Moreirinha, C., Almeida, A., Ferreira, V. F., Cavaleiro, J. A. S., & Tomé, J. P. C. (2017). Efficient catalytic oxidation of 3-arylthio- and 3-cyclohexylthio-lapachone derivatives to new sulfonyl derivatives and evaluation of their antibacterial activities. Molecules, 22(2), Article 302. https://doi.org/10.3390/molecules22020302

@article{80a3df7525f14d95ba2828486c99e548,

title = "Efficient catalytic oxidation of 3-arylthio- and 3-cyclohexylthio-lapachone derivatives to new sulfonyl derivatives and evaluation of their antibacterial activities",

abstract = "New sulfonyl-lapachones were efficiently obtained through the catalytic oxidation of arylthio- and cyclohexylthio-lapachone derivatives with hydrogen peroxide in the presence of a Mn(III) porphyrin complex. The antibacterial activities of the non-oxidized and oxidized lapachone derivatives against the Gram-negative bacteria Escherichia coli and the Gram-positive bacteria Staphylococcus aureus were evaluated after their incorporation into polyvinylpyrrolidone (PVP) micelles. The obtained results show that the PVP-formulations of the lapachones 4b-g and of the sulfonyl-lapachones 7e and 7g reduced the growth of S. aureus.",

keywords = "Antibacterial activity, Arylthio/cyclohexylthio-lapachones, Hydrogen peroxide, Oxidation, Polyvinylpyrrolidone, PorphyrinatoMn(III), Sulfonyl-lapachones",

author = "Cardoso, \{Mariana F.Do C.\} and Gomes, \{Ana T.P.C.\} and Moreira, \{Caroline Dos S.\} and Sim{\~o}es, \{M{\'a}rio M.Q.\} and Neves, \{Maria G.P.M.S.\} and \{Da Rocha\}, \{David R.\} and \{Da Silva\}, \{Fernando De C.\} and Catarina Moreirinha and Adelaide Almeida and Ferreira, \{Vitor F.\} and Cavaleiro, \{Jos{\'e} A.S.\} and Tom{\'e}, \{Jo{\~a}o Paulo C.\}",

note = "Publisher Copyright: {\textcopyright} 2017 by the authors; licensee MDPI, Basel, Switzerland.",

year = "2017",

month = feb,

doi = "10.3390/molecules22020302",

language = "English",

volume = "22",

journal = "Molecules",

issn = "1420-3049",

publisher = "MDPI",

number = "2",

}

Cardoso, MFDC, Gomes, ATPC, Moreira, CDS, Simões, MMQ, Neves, MGPMS, Da Rocha, DR, Da Silva, FDC, Moreirinha, C, Almeida, A, Ferreira, VF, Cavaleiro, JAS & Tomé, JPC 2017, 'Efficient catalytic oxidation of 3-arylthio- and 3-cyclohexylthio-lapachone derivatives to new sulfonyl derivatives and evaluation of their antibacterial activities', Molecules, vol. 22, no. 2, 302. https://doi.org/10.3390/molecules22020302

TY - JOUR

T1 - Efficient catalytic oxidation of 3-arylthio- and 3-cyclohexylthio-lapachone derivatives to new sulfonyl derivatives and evaluation of their antibacterial activities

AU - Cardoso, Mariana F.Do C.

AU - Gomes, Ana T.P.C.

AU - Moreira, Caroline Dos S.

AU - Simões, Mário M.Q.

AU - Neves, Maria G.P.M.S.

AU - Da Rocha, David R.

AU - Da Silva, Fernando De C.

AU - Moreirinha, Catarina

AU - Almeida, Adelaide

AU - Ferreira, Vitor F.

AU - Cavaleiro, José A.S.

AU - Tomé, João Paulo C.

PY - 2017/2

Y1 - 2017/2

N2 - New sulfonyl-lapachones were efficiently obtained through the catalytic oxidation of arylthio- and cyclohexylthio-lapachone derivatives with hydrogen peroxide in the presence of a Mn(III) porphyrin complex. The antibacterial activities of the non-oxidized and oxidized lapachone derivatives against the Gram-negative bacteria Escherichia coli and the Gram-positive bacteria Staphylococcus aureus were evaluated after their incorporation into polyvinylpyrrolidone (PVP) micelles. The obtained results show that the PVP-formulations of the lapachones 4b-g and of the sulfonyl-lapachones 7e and 7g reduced the growth of S. aureus.

AB - New sulfonyl-lapachones were efficiently obtained through the catalytic oxidation of arylthio- and cyclohexylthio-lapachone derivatives with hydrogen peroxide in the presence of a Mn(III) porphyrin complex. The antibacterial activities of the non-oxidized and oxidized lapachone derivatives against the Gram-negative bacteria Escherichia coli and the Gram-positive bacteria Staphylococcus aureus were evaluated after their incorporation into polyvinylpyrrolidone (PVP) micelles. The obtained results show that the PVP-formulations of the lapachones 4b-g and of the sulfonyl-lapachones 7e and 7g reduced the growth of S. aureus.

KW - Antibacterial activity

KW - Arylthio/cyclohexylthio-lapachones

KW - Hydrogen peroxide

KW - Oxidation

KW - Polyvinylpyrrolidone

KW - PorphyrinatoMn(III)

KW - Sulfonyl-lapachones

UR - https://www.scopus.com/pages/publications/85013187596

U2 - 10.3390/molecules22020302

DO - 10.3390/molecules22020302

M3 - Article

C2 - 28212345

AN - SCOPUS:85013187596

SN - 1420-3049

VL - 22

JO - Molecules

JF - Molecules

IS - 2

M1 - 302

ER -

Efficient catalytic oxidation of 3-arylthio- and 3-cyclohexylthio-lapachone derivatives to new sulfonyl derivatives and evaluation of their antibacterial activities

Abstract

Keywords

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