Optimisation of the method for measuring lipophilicity of tripyridylporphyrin

Ovaj rad daje pregled o metodama koje bi se mogle koristiti za mjerenje lipofilnosti tripiridilporfirina. Porfirini su potencijalno dobri fotosenzibilizatori koji se koriste u fotodinamičkoj terapiji jer imaju dobra fotofizička svojstva te im je sinteza jednostavna. Važnost ispitivanja lipofilnosti proizlazi iz toga što je odlika dobrog fotosenzibilizatora selektivnost na tumorske stanice, a na to utječe lipofilnost. Lipofilnost se mjeri kao distribucija molekule lijeka između organske faze (oktan-1-ol) i vodene faze izražena kao logP. Dakle, u radu se određivala vrijednost logP u različitim otapalima u usporedbi s referentnom vrijednošću oktan-1-ola i vode. Korištena su dva spoja: 5-(4-oktadekanamidofenil)-10,15,20-tris(1-oksido-3-piridil)porfirin i 5-(4-amidofenil)-10,15,20-tris(1-oksido-3-piridil)porfirin i šest različitih otapala koja su uključivala: metanol, butan-1-ol, oktan-1-ol, oktan-2-ol, PBS (engl.phpsphate buffer saline) i vodu. Eksperimentalni dio se sastoji od dva dijela. U prvom djelu je ispitivana topljivost ova dva navedena spoja u otapalima pomoću UV-Vis spektroskopije, dobiven je apsorpcijski spektar iz kojeg je onda izračunat molarni apsorpcijski koeficijent koji je u daljnjem postupku korišten za izračunavanje vrijednosti particijskog koeficijenta. Drugi dio eksperimenta uključivao je određivanje Rf vrijednosti pomoću tankoslojne kromatografije te upotrebu „shake-flask“ metode za konačno određivanje particijskog koeficijenta. Rezultati su pokazali da se ova dva spoja najbolje otapaju u butan-1-olu . i da je ovo otapalo, u kombinaciji s referentnim oktan-1-olom, optimalno za određivanje logP vrijednosti za tripiridilporfirine.This paper provides an overview of methods that could be used to measure the lipophilicity of tripyridylporphyrins. Porphyrins are potentially good photosensitizers used in photodynamic therapy because they have good photophysical properties and their synthesis is simple. The importance of lipophilicity testing stems from the fact that a good photosensitizer is characterized by selectivity for tumor cells, which is influenced by lipophilicity. Lipophilicity is measured as the distribution of a drug molecule between the organic phase (octan-1-ol) and the aqueous phase expressed as logP. Thus, the logP value in different solvents was determined in comparison with the reference value of octan-1-ol and water. Two compounds were used: 5- (4-octadecanamidophenyl) -10,15,20-tris (1-oxido-3-pyridyl) porphyrin and 5- (4-amidophenyl) -10,15,20-tris (1-oxido) -3-pyridyl) porphyrin and six different solvents which included: methanol, butan-1-ol, octan-1-ol, octan-2-ol, PBS (phpsphate buffer saline) and water. The experimental part consists of two parts. In the first part, the solubility of these two compounds in solvents was examined by UV-Vis spectroscopy, the absorption spectrum was obtained from which the molar absorption coefficient was then calculated, which was used in the further procedure to calculate the values of the partition coefficient. The second part of the experiment involved determining the Rf value by thin layer chromatography and using the shake-flask method to finally determine the partition coefficient. The results showed that these two compounds were best dissolved in butan-1-ol. and that this solvent, in combination with the reference octan-1-ol, is optimal for determining the logP value for tripyridylporphyrins