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AGGREGATION OF 2,3‐DIHYDROXY‐ETIOCHLORIN I. AN AMPHIPHILIC MODEL COMPOUND FOR PHOTODYNAMIC THERAPY AND GREEN HEME d
Author(s) -
Senge Mathias O.,
Hope Hakon,
Iakovides Panos,
Smith Kevin M.
Publication year - 1993
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1993.tb04963.x
Subject(s) - chemistry , monoclinic crystal system , intramolecular force , heme , hydrogen bond , crystal structure , stereochemistry , molecule , amphiphile , pyrrole , crystallography , organic chemistry , copolymer , enzyme , polymer
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) Å, b = 26.430(9) Å, c = 10.823(5), β= 104.47(3) Å, V = 2743(2) Å 3 . The structure was refined to an R ‐value of 0.097 on the basis of 1150 reflections with F > 4.0σ (F) (130 K).