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. 2004 Mar;30(1):83–96. doi: 10.1023/B:JOBP.0000016569.40786.2e

Interactions of Cyclic AMP and Its Dibutyryl Analogue with a Lipid Layer in the Aqueous Mixtures of Monoolein Preparation and Dioleoyl Phosphatidylcholine as Probed by X-Ray Diffraction and Raman Spectroscopy

Zita Talaikytė 1, Justas Barauskas 1,2, Gediminas Niaura 1, Irena Švedaitė 1, Eugenijus Butkus 1, Valdemaras Razumas 1, Tommy Nylander 2
PMCID: PMC3456501  PMID: 23345862

Abstract

Interactions of adenosine 3':5'-cyclicmonophosphate (cAMP) andN6,2'-O-dibutyryladenosine3':5'-cyclic monophosphate (dbcAMP) with alipid layer composed of monoolein-basedpreparation and dioleoylphosphatidylcholine (DOPC) wereinvestigated by small-angle X-raydiffraction (SAXD) and Raman spectroscopy.The reversed hexagonal (HII)MO/DOPC/H2O phase of 65:15:20 wt.%composition was selected as a referencesystem. SAXD revealed that entrapment (atthe expense of water) of 3 wt.% cAMP intothe reference system did not change thepolymorphic form and structural parametersof the phase. The same content of dbcAMPinduced the transition from the HIIphase to the reversed bicontinuous cubicphase of space group Ia3d. Thistransition is explained by the increase oflipid head-group area due to thepenetration of the acylated adenine groupof dbcAMP into the polar/apolar region oflipid layer. The conclusion is supported byRaman spectroscopy, showing thedisruption/weakening of hydrogen bonding inthe MO/DOPC-based matrix at the N1- andN3-sites of the dbcAMP adenine ring. Asdistinct from dbcAMP, cAMP remains mostlyin the water channels of the HIIphase, although the phosphate residue ofnucleotide interacts with the quaternaryammonium group of DOPC. Both nucleotidesincrease the population of gaucheisomers in the DOPC choline group.

Keywords: Cyclic AMP, dibutyryl cyclic AMP, dioleoyl phosphatidylcholine, liquid-crystalline phases, monoolein, Raman spectroscopy, X-ray diffraction

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