title: Aggregation of 2,3-dihydroxy-etiochlorin I. An amphiphilic model compound for photodynamic therapy and green heme d.
abstract: The crystal structure of 2,3-dihydroxy-etiochlorin I has been determined to obtain information on its aggregation behavior. Cis-dihydroxychlorins serve as model compounds for green heme d and show promising photonecrotic activity in photodynamic therapy. The compound shows strong aggregation in the solid state facilitated by intramolecular hydrogen bonding between one hydroxy group and pyrrole nitrogens of neighboring molecules. This novel type of aggregation leads to chain-type aggregates in the crystal. The title compound 4 crystallized in the monoclinic space group Ia (Z = 4) with unit cell dimensions a = 9.902(4) A, b = 26.430(9) A, c = 10.823(5), beta = 104.47(3) A, V = 2743(2) A3. The structure was refined to an R-value of 0.097 on the basis of 1150 reflections with F > 4.0 sigma (F) (130 K).
authors.affiliation: Department of Chemistry, University of California, Davis 95616.
authors.forename: M O
authors.initials: MO
authors.lastname: Senge
authors.forename: H
authors.initials: H
authors.lastname: Hope
authors.forename: P
authors.initials: P
authors.lastname: Iakovides
authors.forename: K M
authors.initials: KM
authors.lastname: Smith
mesh_terms: D005044:Etioporphyrins / Q000737:chemistry*; D006418:Heme / Q000031:analogs & derivatives* / Q000737:chemistry; D008954:Models, Biological; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D017319:Photosensitizing Agents / Q000737:chemistry*; D014961:X-Ray Diffraction
chemical_list: D005044:Etioporphyrins; D017319:Photosensitizing Agents; C085254:2,3-dihydroxyetiochlorin; D006418:Heme; C080647:heme d