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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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

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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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