PMID- 21923179 OWN - NLM STAT- MEDLINE DCOM- 20120315 LR - 20121115 IS - 1520-5207 (Electronic) IS - 1520-5207 (Linking) VI - 115 IP - 43 DP - 2011 Nov 3 TI - UV-absorption spectra of melanosomes containing varying 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid content. PG - 12624-31 LID - 10.1021/jp2060624 [doi] AB - Central to understanding the photochemical properties of melanosomes is a direct measurement of their absorption coefficients. Herein, the absorption spectra of intact melanosomes of varying molecular compositions and embryonic origins were measured and compared over the spectral range from 245 to 310 nm. The absorption spectra of melanosomes predominately comprised of the eumelanin pigment were found to differ significantly from their constituent precursor molecules, 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA). This difference was most notable in the UV-A region and indicates that the electronic structures of the monomeric building blocks, DHICA in particular, are significantly modified upon polymerization to the melanin pigment. Furthermore, in comparing embryonic differences, the absorption coefficients of melanosomes isolated from bovine retinal pigment epithelial (RPE) cells (originating from the primitive forebrain) were greater than those for bovine choroid or iris melanosomes (originating from the neural crest). This difference suggests that either the pigment is present in greater density in RPE melanosomes or that there is an underlying difference in molecular structure. FAU - Peles, Dana N AU - Peles DN AD - Department of Chemistry, Duke University, Durham, North Carolina 27708, United States. FAU - Simon, John D AU - Simon JD LA - eng PT - Journal Article PT - Research Support, Non-U.S. Gov't DEP - 20111010 PL - United States TA - J Phys Chem B JT - The journal of physical chemistry. B JID - 101157530 RN - 0 (Indoles) RN - 0 (Melanins) RN - 12627-86-0 (eumelanin) RN - 4790-08-3 (5,6-dihydroxy-2-indolylcarboxylic acid) RN - Z3OC8499KG (5,6-dihydroxyindole) SB - IM MH - Absorption MH - Animals MH - Cattle MH - Choroid/metabolism MH - Indoles/*chemistry MH - Iris/metabolism MH - Melanins/chemistry MH - Melanosomes/*chemistry MH - Retinal Pigment Epithelium/metabolism MH - Spectrophotometry, Ultraviolet EDAT- 2011/09/20 06:00 MHDA- 2012/03/16 06:00 CRDT- 2011/09/20 06:00 PHST- 2011/09/20 06:00 [entrez] PHST- 2011/09/20 06:00 [pubmed] PHST- 2012/03/16 06:00 [medline] AID - 10.1021/jp2060624 [doi] PST - ppublish SO - J Phys Chem B. 2011 Nov 3;115(43):12624-31. doi: 10.1021/jp2060624. Epub 2011 Oct 10.