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LUND UNIVERSITY LIBRARIES

New antimalarials - Synthesis and characterization of transition metal complexes of two salicylaldimine ligands

Sjölin, Herman LU (2023) KEMK10 20231
Department of Chemistry
Abstract
Introduction: The World Health Organization (WHO) estimates that malaria, the parasitic infection caused by Plasmodium spp., resulted in the deaths of 600,000 people in 2023, predominantly affecting the African region.

Background: In an effort to combat the disease, scientists have turned to heavy metal complexes in search of novel antimalarials. With a rise of resistance against existing antiplasmodial drugs, the world is in need of new therapeutic compounds. Researchers and students at Lund University have worked on quinoline-based ligands for over a decade and multiple compounds have been synthesized, characterized and tested.

Aim: The synthesis and characterization of a quinoline-based, bidentate ligand and six metal-ligand... (More)
Introduction: The World Health Organization (WHO) estimates that malaria, the parasitic infection caused by Plasmodium spp., resulted in the deaths of 600,000 people in 2023, predominantly affecting the African region.

Background: In an effort to combat the disease, scientists have turned to heavy metal complexes in search of novel antimalarials. With a rise of resistance against existing antiplasmodial drugs, the world is in need of new therapeutic compounds. Researchers and students at Lund University have worked on quinoline-based ligands for over a decade and multiple compounds have been synthesized, characterized and tested.

Aim: The synthesis and characterization of a quinoline-based, bidentate ligand and six metal-ligand complexes. The efficacies of the complexes are to be tested externally.

Methods: The ligands were synthesized in two steps respectively, after which the metal complexes were each synthesized in a single step. Characterization of both ligand and metal complex was done by proton FTNMR, FTIR and UV-Vis spectroscopy.

Results}: Recorded data from FTNMR, FTIR and UV-Vis support the successful syntheses of ligands HL1 and HL2, as well as complexes Ru(L1/L2)(p-cymene)Cl, Ir(L1/L2)(Cp*)Cl, Rh(L2)(Cp*)Cl and Pd(L2)2.

Conclusion: Two salicylaldimine ligands (HL1/HL2) were synthesized from quinoline-derivatives with functional groups (OMe, F) at the six position, ethylenediamine and salicylaldehyde. Complexes of L1 (6-Methoxy) with Iridium(III) and Ruthenium(II) were synthesized and characterized by UV-Vis and IR. Further, complexes of L2 (6-Fluoro) with Iridium(III), Rhodium(III), Ruthenium(II) and Pd(II) were synthesized and characterized by UV-Vis, FTIR and FTNMR. (Less)
Popular Abstract (Swedish)
Malaria har över spannet av tusentals år påverkat miljontals människor och resulterade år 2021 i över 600 000 dödsfall, primärt på den afrikanska kontinenten. Symptom orsakas av 5 olika arter av parasitsläktet Plasmodium, som sprids mellan människor via myggor av släktet Anopheles. Efter en förökningsfas i levern invaderar Plasmodium röda blodceller och bryter ner hemoglobin i födovakuolen för att livnära sig. Vid nedbrytningen av hemoglobin frisätts den - för myggan - toxiska heme-B-gruppen. Genom polymeriseringsreaktioner kan parasiten neutralisera fritt Heme och bilda Hemozoin; en Heme-polymer. Användningen av läkemedel som klorokin hindrar polymeriseringen, men har över tiden gett upphov till klorokinresistans. Därför eftersöks... (More)
Malaria har över spannet av tusentals år påverkat miljontals människor och resulterade år 2021 i över 600 000 dödsfall, primärt på den afrikanska kontinenten. Symptom orsakas av 5 olika arter av parasitsläktet Plasmodium, som sprids mellan människor via myggor av släktet Anopheles. Efter en förökningsfas i levern invaderar Plasmodium röda blodceller och bryter ner hemoglobin i födovakuolen för att livnära sig. Vid nedbrytningen av hemoglobin frisätts den - för myggan - toxiska heme-B-gruppen. Genom polymeriseringsreaktioner kan parasiten neutralisera fritt Heme och bilda Hemozoin; en Heme-polymer. Användningen av läkemedel som klorokin hindrar polymeriseringen, men har över tiden gett upphov till klorokinresistans. Därför eftersöks läkemedel mot malaria som uppvisar låg korsresistans med klorokinliknande ämnen hos Plasmodium.

Behandlingen och förebyggandet av malariasymptomen kan härstamma i användningen av barkextrakt från kinaträdet (engelska; chinchona). Långt senare i historien utvecklades och användes det första syntetiska malarialäkemedlet, metylenblått, som var startskottet för utvecklingen av ett flertal andra malarialäkemedel med varierande struktur. Vid Lunds universitet har ett flertal föreningar innehållande tungmetaller utvecklats under det senaste årtiondet, med syftet att kunna behandla malaria.

Målet med kandidatarbetet var att syntetisera tungmetall-innehållande molekyler med potentiell effekt mot klorokininresistanta Plasmodium-varianter. Syntesen och uppreningen av två kinolinderivat utfördes och vidare syntetiserades föreningar av kinolinderivaten med tungmetallerna ruthenium, iridium, rhodium och palladium. Arbetet var lyckat, då ett flertal tungmetallföreningar kunde påvisas spektroskopiskt. (Less)
Please use this url to cite or link to this publication:
author
Sjölin, Herman LU
supervisor
organization
course
KEMK10 20231
year
type
M2 - Bachelor Degree
subject
keywords
bidentate, ligand, malaria, metal, quinoline, chemical physics
language
English
id
9134456
date added to LUP
2023-08-23 08:53:15
date last changed
2023-08-23 08:53:15
@misc{9134456,
  abstract     = {{Introduction: The World Health Organization (WHO) estimates that malaria, the parasitic infection caused by Plasmodium spp., resulted in the deaths of 600,000 people in 2023, predominantly affecting the African region.

Background: In an effort to combat the disease, scientists have turned to heavy metal complexes in search of novel antimalarials. With a rise of resistance against existing antiplasmodial drugs, the world is in need of new therapeutic compounds. Researchers and students at Lund University have worked on quinoline-based ligands for over a decade and multiple compounds have been synthesized, characterized and tested.

Aim: The synthesis and characterization of a quinoline-based, bidentate ligand and six metal-ligand complexes. The efficacies of the complexes are to be tested externally.

Methods: The ligands were synthesized in two steps respectively, after which the metal complexes were each synthesized in a single step. Characterization of both ligand and metal complex was done by proton FTNMR, FTIR and UV-Vis spectroscopy.

Results}: Recorded data from FTNMR, FTIR and UV-Vis support the successful syntheses of ligands HL1 and HL2, as well as complexes Ru(L1/L2)(p-cymene)Cl, Ir(L1/L2)(Cp*)Cl, Rh(L2)(Cp*)Cl and Pd(L2)2.

Conclusion: Two salicylaldimine ligands (HL1/HL2) were synthesized from quinoline-derivatives with functional groups (OMe, F) at the six position, ethylenediamine and salicylaldehyde. Complexes of L1 (6-Methoxy) with Iridium(III) and Ruthenium(II) were synthesized and characterized by UV-Vis and IR. Further, complexes of L2 (6-Fluoro) with Iridium(III), Rhodium(III), Ruthenium(II) and Pd(II) were synthesized and characterized by UV-Vis, FTIR and FTNMR.}},
  author       = {{Sjölin, Herman}},
  language     = {{eng}},
  note         = {{Student Paper}},
  title        = {{New antimalarials - Synthesis and characterization of transition metal complexes of two salicylaldimine ligands}},
  year         = {{2023}},
}