title: Dual Functioning Thieno-Pyrrole Fused BODIPY Dyes for NIR Optical Imaging and Photodynamic Therapy: Singlet Oxygen Generation without Heavy Halogen Atom Assistance.
abstract: We discovered a rare phenomenon wherein a thieno-pyrrole fused BODIPY dye (SBDPiR690) generates singlet oxygen without heavy halogen atom substituents. SBDPiR690 generates both singlet oxygen and fluorescence. To our knowledge, this is the first example of such a finding. To establish a structure-photophysical property relationship, we prepared SBDPiR analogs with electron-withdrawing groups at the para-position of the phenyl groups. The electron-withdrawing groups increased the HOMO-LUMO energy gap and singlet oxygen generation. Among the analogs, SBDPiR688, a CF3 analog, had an excellent dual functionality of brightness (82290 m(-1)  cm(-1) ) and phototoxic power (99170 m(-1)  cm(-1) ) comparable to those of Pc 4, due to a high extinction coefficient (211 000 m(-1)  cm(-1) ) and balanced decay (Φflu =0.39 and ΦΔ =0.47). The dual functionality of the lead compound SBDPiR690 was successfully applied to preclinical optical imaging and for PDT to effectively control a subcutaneous tumor.
authors.affiliation: Department of Pharmaceutical Sciences, University of Oklahoma Health Sciences Center, 1110 North Stonewall Ave, Oklahoma City, OK, 73117, USA.
authors.forename: Ryan L
authors.initials: RL
authors.lastname: Watley
authors.affiliation: Department of Pharmaceutical Sciences, University of Oklahoma Health Sciences Center, 1110 North Stonewall Ave, Oklahoma City, OK, 73117, USA.
authors.forename: Samuel G
authors.initials: SG
authors.lastname: Awuah
authors.affiliation: Department of Pharmaceutical Sciences, University of Oklahoma Health Sciences Center, 1110 North Stonewall Ave, Oklahoma City, OK, 73117, USA.
authors.forename: Moses
authors.initials: M
authors.lastname: Bio
authors.affiliation: Department of Chemistry, University of North Texas, 1155 Union Circle, #305070, Denton, TX, 76203-5017, USA.
authors.forename: Robert
authors.initials: R
authors.lastname: Cantu
authors.affiliation: Department of Chemistry, University of North Texas, 1155 Union Circle, #305070, Denton, TX, 76203-5017, USA.
authors.forename: Habtom B
authors.initials: HB
authors.lastname: Gobeze
authors.affiliation: Department of Chemistry, University of North Texas, 1155 Union Circle, #305070, Denton, TX, 76203-5017, USA.
authors.forename: Vladimir N
authors.initials: VN
authors.lastname: Nesterov
authors.affiliation: Department of Chemistry, University of North Texas, 1155 Union Circle, #305070, Denton, TX, 76203-5017, USA.
authors.forename: Sushanta K
authors.initials: SK
authors.lastname: Das
authors.affiliation: Department of Chemistry, University of North Texas, 1155 Union Circle, #305070, Denton, TX, 76203-5017, USA. francis.dsouza@unt.edu.
authors.forename: Francis
authors.initials: F
authors.lastname: D'Souza
authors.affiliation: Department of Pharmaceutical Sciences, University of Oklahoma Health Sciences Center, 1110 North Stonewall Ave, Oklahoma City, OK, 73117, USA. youngjae-you@ouhsc.edu.
authors.forename: Youngjae
authors.initials: Y
authors.lastname: You
mesh_terms: D000818:Animals; D017209:Apoptosis / Q000187:drug effects; D001896:Boron Compounds / Q000737:chemistry* / Q000633:toxicity; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D015195:Drug Design; D005456:Fluorescent Dyes / Q000737:chemistry; D006219:Halogens / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry* / Q000633:toxicity; D006801:Humans; D007834:Lasers; D051379:Mice; D008807:Mice, Inbred BALB C; D008819:Mice, Nude; D008968:Molecular Conformation; D009369:Neoplasms / Q000188:drug therapy; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000737:chemistry / Q000627:therapeutic use / Q000633:toxicity; D011758:Pyrroles / Q000737:chemistry*; D011789:Quantum Theory; D026082:Singlet Oxygen / Q000737:chemistry / Q000378:metabolism*; D019265:Spectroscopy, Near-Infrared; D013329:Structure-Activity Relationship; D014183:Transplantation, Heterologous
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; C000605550:5,5-difluoro-2,8-diphenyl-11-(trifluoromethyl)-5H-thieno(2',3'-4,5)pyrrolo(1,2-c)thieno(2',3'-4,5)pyrrolo(2,1-f)(1,3,2)diazaborinin-4-ium-5-uide; D001896:Boron Compounds; D005456:Fluorescent Dyes; D006219:Halogens; D006576:Heterocyclic Compounds, 4 or More Rings; D017319:Photosensitizing Agents; D011758:Pyrroles; D026082:Singlet Oxygen
keywords: BODIPY; fluorescence imaging; photodynamic therapy; singlet oxygen generation; theranostics