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Amphiphilic Porphyrins as Possible PhotodynamicTherapy Sensitizers

  • Kartonierter Einband
  • 140 Seiten
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Although photodynamic therapy with porphyrinic pigments as photosensitizers has emerged as promising modality for disease treatmen... Weiterlesen
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Beschreibung

Although photodynamic therapy with porphyrinic pigments as photosensitizers has emerged as promising modality for disease treatment, there remains a great need for the preparation of more selective sensitizers. Thus, the synthesis of amphiphilic porphyrins bearing fluoro and carboxy substituents was attempted. The most successful were the synthesis of three para-phenyl substituted tetraphenylporphyrins (TPPs) using both rational and statistical methodology. The porphyrins of greatest interest, where carboxy and fluoro substituents were placed at the para positions of opposite or adjacent phenyl rings, were either not obtained or only in small yields. However, 5,10,15-tri(4-fluorophenyl)-20(4-carboxyphenyl)porphyrin was synthesized in higher yields. To derive information on the factors that govern the permeation of this porphyrin across cell membrane mimics and its localization patters, it was allowed to diffuse into unilamellar vesicles at pH 2,7 and 10. The porphyrin incorporated in vesicles only to a small extent at pH 10 demonstrating that a proper amphiphilicity balance is required for porphyrins to incorporate into cell membrane mimics.

Autorentext

Carina Peritore received her B.S. from UCSC with ProfessorBakthan Singaram in Organic Chemistry. She went on to work forProfessor Tony Fink in a Biochemistry Lab at UCSC and thenreceived her M.S. with Professor Ursula Simonis in BioorganicChemistry at SFSU. She is currently a PhD Candidate withProfessor Scott Schaus in Organic Synthesis at BU.



Klappentext

Although photodynamic therapy with porphyrinicpigments as photosensitizers has emerged as promisingmodality for disease treatment, there remains a greatneed for the preparation of more selectivesensitizers. Thus, the synthesis of amphiphilicporphyrins bearing fluoro and carboxy substituentswas attempted. The most successful were the synthesisof three para-phenyl substitutedtetraphenylporphyrins (TPPs) using both rational andstatistical methodology. The porphyrins of greatestinterest, where carboxy and fluoro substituents wereplaced at the para positions of opposite or adjacentphenyl rings, were either not obtained or only insmall yields. However,5,10,15-tri(4-fluorophenyl)-20(4-carboxyphenyl)porphyrinwas synthesized in higher yields. To deriveinformation on the factors that govern the permeationof this porphyrin across cell membrane mimics and itslocalization patters, it was allowed to diffuse intounilamellar vesicles at pH 2,7 and 10. The porphyrinincorporated in vesicles only to a small extent at pH10 demonstrating that a proper amphiphilicity balanceis required for porphyrins to incorporate into cellmembrane mimics.

Produktinformationen

Titel: Amphiphilic Porphyrins as Possible PhotodynamicTherapy Sensitizers
Untertitel: A Rational versus Statistical Synthesis ofTetraphenylporphyrins bearing fluoro and carboxysubstituents
Autor:
EAN: 9783639151244
ISBN: 978-3-639-15124-4
Format: Kartonierter Einband
Herausgeber: VDM Verlag
Genre: Organische Chemie
Anzahl Seiten: 140
Gewicht: 225g
Größe: H220mm x B150mm x T8mm
Veröffentlichung: 01.05.2009
Jahr: 2009