Properties and behaviour of tetracyclic allopsoralen derivatives inside a DPPC lipid bilayer model.

Allopsoralens are angular psoralen derivatives presenting advantages over the parent compound because of monofunctional DNA-photobinding and consequent lower toxicity. Allopsoralen molecules with three different substituents and different protonation states were studied using the molecular dynamics technique. The location of these molecules when inside the lipid bilayer is of major importance because their photochemical properties can change with the environment. Also, the ability of psoralens to form photoadducts with unsaturated phospholipids depends on the preference of the molecules to locate themselves closer to the bilayer middle were the double bond functionality can be found. Herein we show that the allopsoralens tend to accumulate inside the lipid bilayer closer to the water interface when protonated or closer to the interface middle otherwise. Allopsoralens containing one amine terminated carbon chain tend to have different rotational and orientational behaviour and an orientation preference close to the ones shown by the lipids. The size and chemical nature of the substituent also affect the molecular mobility and capacity to interact with water molecules and the nitrogen or phosphorus atoms of the lipids.

Saenz Mendez, PatriciaUniversidad de la Republic, URY(Swepub:kau)patrmend (författare)
Eriksson, Leif ANational University of Ireland, IRL (författare)
Guedes, Rita CUniversity Lisbon, PRT (författare)
University Lisbon, PRTUniversidad de la Republic, URY (creator_code:org_t)

Ingår i:Physical Chemistry, Chemical Physics - PCCP: Royal Society of Chemistry (RSC)13:21, s. 10174-821463-90761463-9084

Av författaren/redakt...: dos Santos, Dani ...; Saenz Mendez, Pa ...; Eriksson, Leif A; Guedes, Rita C

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