Antimicrobial and cytotoxic activities of 1,2,3-triazole-sucrose derivatives

Krasimira Todorova Markova Petrova, Taterao M. Potewar, Paula Correia-da-Silva, Maria Teresa Barros, Ricardo C. Calheta, Ana Ćiric, Isabel C.F,R. Ferreira

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

A library of 1-(1',2,3,3',4,4',6-hepta-O-acetyl-6'-deoxy-sucros-6'-yl)-1,2,3-triazoles have been investigated for their antibacterial, antifungal and cytotoxic activities. Most of the target compounds showed good inhibitory activity against a variety of clinically and food contaminant important microbial pathogens. In particular, 1-(1',2,3,3',4,4',6-hepta-O-acetyl-6'-deoxy-sucros-6'-yl)-4-(4-pentylphenyl)-1,2,3-triazole (5) was highly active against all the tested bacteria with minimal inhibitory concentrations (MICs) ranging between 1.1 and 4.4 µM and bactericidal concentrations (MBCs) from 2.2 and 8.4 µM. The compound 1-(1',2,3,3',4,4',6-hepta-O-acetyl-6'-deoxy-sucros-6'-yl)-4-(4-bromophenyl)-1,2,3-triazole (3) showed antifungal activity with MICs from 0.6 to 4.8 µM and minimal fungicidal concentrations (MFCs) ranging between 1.2 and 8.9 µM. Furthermore, some of the compounds possessed moderate cytotoxicity against human breast, lung, cervical and hepatocellular carcinoma cell lines, without showing toxicity for non-tumor liver cells. The above mentioned derivatives represent promising leads for the development of new generation of sugar-triazole antifungal agents.
Original languageEnglish
Pages (from-to)66-71
Number of pages6
JournalCarbohydrate Research
Volume417
DOIs
Publication statusPublished - 19 Nov 2015

Fingerprint

Triazoles
Sucrose
Derivatives
Antifungal Agents
Pathogens
Cytotoxicity
Sugars
Liver
Libraries
Toxicity
Hepatocellular Carcinoma
Bacteria
Cells
Impurities
Breast Neoplasms
Cell Line
Food
Lung

Keywords

  • 1,2,3-Triazoles
  • Sucrose
  • Antibacterial activity
  • Antifungal activity
  • Cytotoxic activity

Cite this

Petrova, Krasimira Todorova Markova ; Potewar, Taterao M. ; Correia-da-Silva, Paula ; Barros, Maria Teresa ; Calheta, Ricardo C. ; Ćiric, Ana ; C.F,R. Ferreira, Isabel . / Antimicrobial and cytotoxic activities of 1,2,3-triazole-sucrose derivatives. In: Carbohydrate Research. 2015 ; Vol. 417. pp. 66-71.
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abstract = "A library of 1-(1',2,3,3',4,4',6-hepta-O-acetyl-6'-deoxy-sucros-6'-yl)-1,2,3-triazoles have been investigated for their antibacterial, antifungal and cytotoxic activities. Most of the target compounds showed good inhibitory activity against a variety of clinically and food contaminant important microbial pathogens. In particular, 1-(1',2,3,3',4,4',6-hepta-O-acetyl-6'-deoxy-sucros-6'-yl)-4-(4-pentylphenyl)-1,2,3-triazole (5) was highly active against all the tested bacteria with minimal inhibitory concentrations (MICs) ranging between 1.1 and 4.4 µM and bactericidal concentrations (MBCs) from 2.2 and 8.4 µM. The compound 1-(1',2,3,3',4,4',6-hepta-O-acetyl-6'-deoxy-sucros-6'-yl)-4-(4-bromophenyl)-1,2,3-triazole (3) showed antifungal activity with MICs from 0.6 to 4.8 µM and minimal fungicidal concentrations (MFCs) ranging between 1.2 and 8.9 µM. Furthermore, some of the compounds possessed moderate cytotoxicity against human breast, lung, cervical and hepatocellular carcinoma cell lines, without showing toxicity for non-tumor liver cells. The above mentioned derivatives represent promising leads for the development of new generation of sugar-triazole antifungal agents.",
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Petrova, KTM, Potewar, TM, Correia-da-Silva, P, Barros, MT, Calheta, RC, Ćiric, A & C.F,R. Ferreira, I 2015, 'Antimicrobial and cytotoxic activities of 1,2,3-triazole-sucrose derivatives', Carbohydrate Research, vol. 417, pp. 66-71. https://doi.org/10.1016/j.carres.2015.09.003

Antimicrobial and cytotoxic activities of 1,2,3-triazole-sucrose derivatives. / Petrova, Krasimira Todorova Markova; Potewar, Taterao M.; Correia-da-Silva, Paula; Barros, Maria Teresa; Calheta, Ricardo C. ; Ćiric, Ana ; C.F,R. Ferreira, Isabel .

In: Carbohydrate Research, Vol. 417, 19.11.2015, p. 66-71.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Antimicrobial and cytotoxic activities of 1,2,3-triazole-sucrose derivatives

AU - Petrova, Krasimira Todorova Markova

AU - Potewar, Taterao M.

AU - Correia-da-Silva, Paula

AU - Barros, Maria Teresa

AU - Calheta, Ricardo C.

AU - Ćiric, Ana

AU - C.F,R. Ferreira, Isabel

N1 - Sem PDF. Fundacao para a Ciencia e a Tecnologia (PEst-C/EQB/LA0006/2013; PEst-OE/AGR/UI0690/2014; SFRH/BPD/65173/2009; SFRH/BPD/68344/2010; RECI/BBB-BQB/0230/2012); Serbian Ministry of Education, Science and Technological Development (173032)

PY - 2015/11/19

Y1 - 2015/11/19

N2 - A library of 1-(1',2,3,3',4,4',6-hepta-O-acetyl-6'-deoxy-sucros-6'-yl)-1,2,3-triazoles have been investigated for their antibacterial, antifungal and cytotoxic activities. Most of the target compounds showed good inhibitory activity against a variety of clinically and food contaminant important microbial pathogens. In particular, 1-(1',2,3,3',4,4',6-hepta-O-acetyl-6'-deoxy-sucros-6'-yl)-4-(4-pentylphenyl)-1,2,3-triazole (5) was highly active against all the tested bacteria with minimal inhibitory concentrations (MICs) ranging between 1.1 and 4.4 µM and bactericidal concentrations (MBCs) from 2.2 and 8.4 µM. The compound 1-(1',2,3,3',4,4',6-hepta-O-acetyl-6'-deoxy-sucros-6'-yl)-4-(4-bromophenyl)-1,2,3-triazole (3) showed antifungal activity with MICs from 0.6 to 4.8 µM and minimal fungicidal concentrations (MFCs) ranging between 1.2 and 8.9 µM. Furthermore, some of the compounds possessed moderate cytotoxicity against human breast, lung, cervical and hepatocellular carcinoma cell lines, without showing toxicity for non-tumor liver cells. The above mentioned derivatives represent promising leads for the development of new generation of sugar-triazole antifungal agents.

AB - A library of 1-(1',2,3,3',4,4',6-hepta-O-acetyl-6'-deoxy-sucros-6'-yl)-1,2,3-triazoles have been investigated for their antibacterial, antifungal and cytotoxic activities. Most of the target compounds showed good inhibitory activity against a variety of clinically and food contaminant important microbial pathogens. In particular, 1-(1',2,3,3',4,4',6-hepta-O-acetyl-6'-deoxy-sucros-6'-yl)-4-(4-pentylphenyl)-1,2,3-triazole (5) was highly active against all the tested bacteria with minimal inhibitory concentrations (MICs) ranging between 1.1 and 4.4 µM and bactericidal concentrations (MBCs) from 2.2 and 8.4 µM. The compound 1-(1',2,3,3',4,4',6-hepta-O-acetyl-6'-deoxy-sucros-6'-yl)-4-(4-bromophenyl)-1,2,3-triazole (3) showed antifungal activity with MICs from 0.6 to 4.8 µM and minimal fungicidal concentrations (MFCs) ranging between 1.2 and 8.9 µM. Furthermore, some of the compounds possessed moderate cytotoxicity against human breast, lung, cervical and hepatocellular carcinoma cell lines, without showing toxicity for non-tumor liver cells. The above mentioned derivatives represent promising leads for the development of new generation of sugar-triazole antifungal agents.

KW - 1,2,3-Triazoles

KW - Sucrose

KW - Antibacterial activity

KW - Antifungal activity

KW - Cytotoxic activity

U2 - 10.1016/j.carres.2015.09.003

DO - 10.1016/j.carres.2015.09.003

M3 - Article

VL - 417

SP - 66

EP - 71

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

ER -