Synthesis and evaluation of hybrid drugs for a potential HIV/AIDS-malaria combination therapy

Malaria and HIV are among the most important global health problems of our time and together are responsible for approximately 3 million deaths annually. These two diseases overlap in many regions of the world including sub-Saharan Africa, Southeast Asia and South America, leading to a higher risk o...

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Published inBioorganic & medicinal chemistry Vol. 20; no. 17; pp. 5277 - 5289
Main Authors Aminake, Makoah N., Mahajan, Aman, Kumar, Vipan, Hans, Renate, Wiesner, Lubbe, Taylor, Dale, de Kock, Carmen, Grobler, Anne, Smith, Peter J., Kirschner, Marc, Rethwilm, Axel, Pradel, Gabriele, Chibale, Kelly
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.09.2012
Elsevier
Subjects
Acquired Immunodeficiency Syndrome - drug therapy
Animals
Anti-HIV Agents - administration & dosage
Anti-HIV Agents - chemical synthesis
Anti-HIV Agents - pharmacology
antimalarials
Antimalarials - administration & dosage
Antimalarials - chemical synthesis
Antimalarials - pharmacology
Biochemistry & Molecular Biology
Biological and medical sciences
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Combination therapy
Dose-Response Relationship, Drug
Drug metabolism
Drug Therapy, Combination
drugs
HeLa Cells
HIV Infections - drug therapy
HIV-1 - drug effects
HIV/AIDS
Human immunodeficiency virus
Humans
Hybrid drugs
Life Sciences & Biomedicine
Malaria
Malaria - drug therapy
Male
Medical sciences
Medicinal chemistry
Mice
Mice, Inbred C57BL
mixed infection
Molecular Structure
oral administration
Parasitic Sensitivity Tests
Pharmacokinetics
Pharmacology & Pharmacy
Pharmacology. Drug treatments
Physical Sciences
Plasmodium berghei
Plasmodium falciparum
Plasmodium falciparum - drug effects
risk
Science & Technology
Structure-Activity Relationship
therapeutics
toxicity
South America
South East Asia
Sub-Saharan Africa
Southeast Asia
Africa
HIV/AIDS
Medicinal chemistry
Malaria
Drug metabolism
Combination therapy
Pharmacokinetics
Hybrid drugs
VIRUS TYPE-1 HIV-1
LACTATE-DEHYDROGENASE
DIHYDROARTEMISININ
CHLOROQUINE
PLASMODIUM-FALCIPARUM MALARIA
METABOLISM
IN-VIVO
HIV REVERSE-TRANSCRIPTASE
DUAL INHIBITORS
BLOOD
Drug
Immunopathology
Evaluation
Protozoal disease
AIDS
Parasitosis
Metabolism
Immune deficiency
Infection
Viral disease
Combined treatment
Chemical synthesis
Hybrid molecule
Online AccessGet full text

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Abstract Malaria and HIV are among the most important global health problems of our time and together are responsible for approximately 3 million deaths annually. These two diseases overlap in many regions of the world including sub-Saharan Africa, Southeast Asia and South America, leading to a higher risk of co-infection. In this study, we generated and characterized hybrid molecules to target Plasmodium falciparum and HIV simultaneously for a potential HIV/malaria combination therapy. Hybrid molecules were synthesized by the covalent fusion of azidothymidine (AZT) with dihydroartemisinin (DHA), a tetraoxane or a 4-aminoquinoline derivative; and the small library was tested for antiviral and antimalarial activity. Our data suggests that compound 7 is the most potent molecule in vitro, with antiplasmodial activity comparable to that of DHA (IC50=26nM, SI>3000), a moderate activity against HIV (IC50=2.9μM; SI>35) and not toxic to HeLa cells at concentrations used in the assay (CC50>100μM). Pharmacokinetics studies further revealed that compound 7 is metabolically unstable and is cleaved via O-dealkylation. These studies account for the lack of in vivo efficacy of compound 7 against the CQ-sensitive Plasmodium berghei N strain in mice, when administered orally at 20mg/kg.
AbstractList Malaria and HIV are among the most important global health problems of our time and together are responsible for approximately 3 million deaths annually. These two diseases overlap in many regions of the world including sub-Saharan Africa, Southeast Asia and South America, leading to a higher risk of co-infection. In this study, we generated and characterized hybrid molecules to target Plasmodium falciparum and HIV simultaneously for a potential HIV/malaria combination therapy. Hybrid molecules were synthesized by the covalent fusion of azidothymidine (AZT) with dihydroartemisinin (DHA), a tetraoxane or a 4-aminoquinoline derivative; and the small library was tested for antiviral and antimalarial activity. Our data suggests that compound 7 is the most potent molecule in vitro, with antiplasmodial activity comparable to that of DHA (IC(50)=26 nM, SI>3000), a moderate activity against HIV (IC(50)=2.9 μM; SI>35) and not toxic to HeLa cells at concentrations used in the assay (CC(50)>100 μM). Pharmacokinetics studies further revealed that compound 7 is metabolically unstable and is cleaved via O-dealkylation. These studies account for the lack of in vivo efficacy of compound 7 against the CQ-sensitive Plasmodium berghei N strain in mice, when administered orally at 20mg/kg.
Malaria and HIV are among the most important global health problems of our time and together are responsible for approximately 3 million deaths annually. These two diseases overlap in many regions of the world including sub-Saharan Africa, Southeast Asia and South America, leading to a higher risk of co-infection. In this study, we generated and characterized hybrid molecules to target Plasmodium falciparum and HIV simultaneously for a potential HIV/malaria combination therapy. Hybrid molecules were synthesized by the covalent fusion of azidothymidine (AZT) with dihydroartemisinin (DHA), a tetraoxane or a 4-aminoquinoline derivative; and the small library was tested for antiviral and antimalarial activity. Our data suggests that compound 7 is the most potent molecule in vitro, with antiplasmodial activity comparable to that of DHA (IC50 = 26 nM, SI >3000), a moderate activity against HIV (IC50 = 2.9 mu M; SI >35) and not toxic to HeLa cells at concentrations used in the assay (CC50 >100 mu M). Pharmacokinetics studies further revealed that compound 7 is metabolically unstable and is cleaved via O-dealkylation. These studies account for the lack of in vivo efficacy of compound 7 against the CQ-sensitive Plasmodium berghei N strain in mice, when administered orally at 20 mg/kg.
Malaria and HIV are among the most important global health problems of our time and together are responsible for approximately 3 million deaths annually. These two diseases overlap in many regions of the world including sub-Saharan Africa, Southeast Asia and South America, leading to a higher risk of co-infection. In this study, we generated and characterized hybrid molecules to target Plasmodium falciparum and HIV simultaneously for a potential HIV/malaria combination therapy. Hybrid molecules were synthesized by the covalent fusion of azidothymidine (AZT) with dihydroartemisinin (DHA), a tetraoxane or a 4-aminoquinoline derivative; and the small library was tested for antiviral and antimalarial activity. Our data suggests that compound 7 is the most potent molecule in vitro, with antiplasmodial activity comparable to that of DHA (IC₅₀=26nM, SI>3000), a moderate activity against HIV (IC₅₀=2.9μM; SI>35) and not toxic to HeLa cells at concentrations used in the assay (CC₅₀>100μM). Pharmacokinetics studies further revealed that compound 7 is metabolically unstable and is cleaved via O-dealkylation. These studies account for the lack of in vivo efficacy of compound 7 against the CQ-sensitive Plasmodium berghei N strain in mice, when administered orally at 20mg/kg.
Malaria and HIV are among the most important global health problems of our time and together are responsible for approximately 3 million deaths annually. These two diseases overlap in many regions of the world including sub-Saharan Africa, Southeast Asia and South America, leading to a higher risk of co-infection. In this study, we generated and characterized hybrid molecules to target Plasmodium falciparum and HIV simultaneously for a potential HIV/malaria combination therapy. Hybrid molecules were synthesized by the covalent fusion of azidothymidine (AZT) with dihydroartemisinin (DHA), a tetraoxane or a 4-aminoquinoline derivative; and the small library was tested for antiviral and antimalarial activity. Our data suggests that compound 7 is the most potent molecule in vitro, with antiplasmodial activity comparable to that of DHA (IC50 = 26 nM, SI >3000), a moderate activity against HIV (IC50 = 2.9 mu M; SI >35) and not toxic to HeLa cells at concentrations used in the assay (CC50 >100 mu M). Pharmacokinetics studies further revealed that compound 7 is metabolically unstable and is cleaved via O-dealkylation. These studies account for the lack of in vivo efficacy of compound 7 against the CQ-sensitive Plasmodium berghei N strain in mice, when administered orally at 20 mg/kg. (C) 2012 Elsevier Ltd. All rights reserved.
Malaria and HIV are among the most important global health problems of our time and together are responsible for approximately 3 million deaths annually. These two diseases overlap in many regions of the world including sub-Saharan Africa, Southeast Asia and South America, leading to a higher risk of co-infection. In this study, we generated and characterized hybrid molecules to target Plasmodium falciparum and HIV simultaneously for a potential HIV/malaria combination therapy. Hybrid molecules were synthesized by the covalent fusion of azidothymidine (AZT) with dihydroartemisinin (DHA), a tetraoxane or a 4-aminoquinoline derivative; and the small library was tested for antiviral and antimalarial activity. Our data suggests that compound 7 is the most potent molecule in vitro, with antiplasmodial activity comparable to that of DHA (IC50=26nM, SI>3000), a moderate activity against HIV (IC50=2.9μM; SI>35) and not toxic to HeLa cells at concentrations used in the assay (CC50>100μM). Pharmacokinetics studies further revealed that compound 7 is metabolically unstable and is cleaved via O-dealkylation. These studies account for the lack of in vivo efficacy of compound 7 against the CQ-sensitive Plasmodium berghei N strain in mice, when administered orally at 20mg/kg.
Author Smith, Peter J.
Taylor, Dale
Kumar, Vipan
de Kock, Carmen
Aminake, Makoah N.
Mahajan, Aman
Chibale, Kelly
Wiesner, Lubbe
Rethwilm, Axel
Pradel, Gabriele
Hans, Renate
Kirschner, Marc
Grobler, Anne
Author_xml – sequence: 1
  givenname: Makoah N.
  surname: Aminake
  fullname: Aminake, Makoah N.
  organization: University of Würzburg, Research Center for Infectious Diseases, Josef-Schneider-Str. 2/D15, 97080 Würzburg, Germany
– sequence: 2
  givenname: Aman
  surname: Mahajan
  fullname: Mahajan, Aman
  organization: Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa
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  givenname: Vipan
  surname: Kumar
  fullname: Kumar, Vipan
  organization: Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, India
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  givenname: Renate
  surname: Hans
  fullname: Hans, Renate
  organization: Department of Chemistry and Biochemistry, University of Namibia, Windhoek, Namibia
– sequence: 5
  givenname: Lubbe
  surname: Wiesner
  fullname: Wiesner, Lubbe
  organization: Division of Pharmacology, University of Cape Town, Observatory 7925, South Africa
– sequence: 6
  givenname: Dale
  surname: Taylor
  fullname: Taylor, Dale
  organization: Division of Pharmacology, University of Cape Town, Observatory 7925, South Africa
– sequence: 7
  givenname: Carmen
  surname: de Kock
  fullname: de Kock, Carmen
  organization: Division of Pharmacology, University of Cape Town, Observatory 7925, South Africa
– sequence: 8
  givenname: Anne
  surname: Grobler
  fullname: Grobler, Anne
  organization: North West University, Potchefstroom Campus, Potchefstroom 2520, South Africa
– sequence: 9
  givenname: Peter J.
  surname: Smith
  fullname: Smith, Peter J.
  organization: Division of Pharmacology, University of Cape Town, Observatory 7925, South Africa
– sequence: 10
  givenname: Marc
  surname: Kirschner
  fullname: Kirschner, Marc
  organization: University of Würzburg, Institute for Virology and Immunbiology, Versbacher Str. 7, 97078 Würzburg, Germany
– sequence: 11
  givenname: Axel
  surname: Rethwilm
  fullname: Rethwilm, Axel
  organization: University of Würzburg, Institute for Virology and Immunbiology, Versbacher Str. 7, 97078 Würzburg, Germany
– sequence: 12
  givenname: Gabriele
  surname: Pradel
  fullname: Pradel, Gabriele
  organization: University of Würzburg, Research Center for Infectious Diseases, Josef-Schneider-Str. 2/D15, 97080 Würzburg, Germany
– sequence: 13
  givenname: Kelly
  surname: Chibale
  fullname: Chibale, Kelly
  email: Kelly.Chibale@uct.ac.za
  organization: Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa
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Issue 17
Keywords HIV/AIDS
Medicinal chemistry
Malaria
Drug metabolism
Combination therapy
Pharmacokinetics
Hybrid drugs
VIRUS TYPE-1 HIV-1
LACTATE-DEHYDROGENASE
DIHYDROARTEMISININ
CHLOROQUINE
PLASMODIUM-FALCIPARUM MALARIA
METABOLISM
IN-VIVO
HIV REVERSE-TRANSCRIPTASE
DUAL INHIBITORS
BLOOD
Drug
Immunopathology
Evaluation
Protozoal disease
AIDS
Parasitosis
Metabolism
Immune deficiency
Infection
Viral disease
Combined treatment
Chemical synthesis
Hybrid molecule
Language English
License CC BY 4.0
Copyright © 2012 Elsevier Ltd. All rights reserved.
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Snippet Malaria and HIV are among the most important global health problems of our time and together are responsible for approximately 3 million deaths annually. These...
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StartPage 5277
SubjectTerms Acquired Immunodeficiency Syndrome - drug therapy
Animals
Anti-HIV Agents - administration & dosage
Anti-HIV Agents - chemical synthesis
Anti-HIV Agents - pharmacology
antimalarials
Antimalarials - administration & dosage
Antimalarials - chemical synthesis
Antimalarials - pharmacology
Biochemistry & Molecular Biology
Biological and medical sciences
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Combination therapy
Dose-Response Relationship, Drug
Drug metabolism
Drug Therapy, Combination
drugs
HeLa Cells
HIV Infections - drug therapy
HIV-1 - drug effects
HIV/AIDS
Human immunodeficiency virus
Humans
Hybrid drugs
Life Sciences & Biomedicine
Malaria
Malaria - drug therapy
Male
Medical sciences
Medicinal chemistry
Mice
Mice, Inbred C57BL
mixed infection
Molecular Structure
oral administration
Parasitic Sensitivity Tests
Pharmacokinetics
Pharmacology & Pharmacy
Pharmacology. Drug treatments
Physical Sciences
Plasmodium berghei
Plasmodium falciparum
Plasmodium falciparum - drug effects
risk
Science & Technology
Structure-Activity Relationship
therapeutics
toxicity
Title Synthesis and evaluation of hybrid drugs for a potential HIV/AIDS-malaria combination therapy
URI https://dx.doi.org/10.1016/j.bmc.2012.06.038
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