title: The nitrodibenzofuran chromophore: a new caging group for ultra-efficient photolysis in living cells.
abstract: Photochemical uncaging of bio-active molecules was introduced in 1977, but since then, there has been no substantial improvement in the properties of generic caging chromophores. We have developed a new chromophore, nitrodibenzofuran (NDBF) for ultra-efficient uncaging of second messengers inside cells. Photolysis of a NDBF derivative of EGTA (caged calcium) is about 16-160 times more efficient than photolysis of the most widely used caged compounds (the quantum yield of photolysis is 0.7 and the extinction coefficient is 18,400 M(-1) cm(-1)). Ultraviolet (UV)-laser photolysis of NDBF-EGTA:Ca(2+) rapidly released Ca(2+) (rate of 20,000 s(-1)) and initiated contraction of skinned guinea pig cardiac muscle. NDBF-EGTA has a two-photon cross-section of approximately 0.6 GM and two-photon photolysis induced localized Ca(2+)-induced Ca(2+) release from the sarcoplasmic recticulum of intact cardiac myocytes. Thus, the NDBF chromophore has great promise as a generic and photochemically efficient protecting group for both one- and two-photon uncaging in living cells.
authors.affiliation: Department of Pharmacology and Physiology, Drexel University College of Medicine, 245 North 15th St., Philadelphia, Pennsylvania 19102, USA.
authors.forename: Atsuya
authors.initials: A
authors.lastname: Momotake
authors.forename: Nicolas
authors.initials: N
authors.lastname: Lindegger
authors.forename: Ernst
authors.initials: E
authors.lastname: Niggli
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Barsotti
authors.forename: Graham C R
authors.initials: GC
authors.lastname: Ellis-Davies
mesh_terms: D000818:Animals; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry*; D002118:Calcium / Q000737:chemistry / Q000378:metabolism*; D020013:Calcium Signaling; D004533:Egtazic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006168:Guinea Pigs; D007834:Lasers; D009200:Myocardial Contraction; D009206:Myocardium / Q000166:cytology / Q000378:metabolism; D032383:Myocytes, Cardiac / Q000378:metabolism / Q000528:radiation effects; D010782:Photolysis; D017785:Photons; D012519:Sarcoplasmic Reticulum / Q000378:metabolism; D014466:Ultraviolet Rays
chemical_list: C507804:3,12-bis(carboxymethyl)-5-(3-nitrodibenzo(b,d)furan-2-yl)-6,9-Dioxa-3,12-diazatetradecanedioic acid; D001572:Benzofurans; D004533:Egtazic Acid; D002118:Calcium