title: Synthesis and assessment of a maleimide functionalized BF2 azadipyrromethene near-infrared fluorochrome.
abstract: The first water soluble maleimide bearing NIR BF2-azadipyrromethene (NIR-AZA) fluorochrome has been synthesised which is capable of rapid thiol conjugations in water with peptides such as glutathione, the cell penetrating peptide (CPP) C(β-A)SKKKKTKV-NH2 and a thiol substituted cRGD. NIR fluorescence imaging showed rapid cellular delivery of the CPP conjugate and effective in vivo tumour localization for the cRGD conjugate.
authors.affiliation: Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen's Green, Dublin 2, Ireland. donalfoshea@rcsi.ie.
authors.forename: Dan
authors.initials: D
authors.lastname: Wu
authors.forename: Shane
authors.initials: S
authors.lastname: Cheung
authors.forename: Marc
authors.initials: M
authors.lastname: Devocelle
authors.forename: Li-Jun
authors.initials: LJ
authors.lastname: Zhang
authors.forename: Zhi-Long
authors.initials: ZL
authors.lastname: Chen
authors.forename: Donal F
authors.initials: DF
authors.lastname: O'Shea
mesh_terms: D000818:Animals; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics; D005978:Glutathione / Q000737:chemistry / Q000493:pharmacokinetics; D006367:HeLa Cells; D006801:Humans; D007259:Infrared Rays; D008301:Maleimides / Q000737:chemistry* / Q000493:pharmacokinetics; D051379:Mice; D015394:Molecular Structure; D009374:Neoplasms, Experimental / Q000378:metabolism; D010456:Peptides, Cyclic / Q000737:chemistry / Q000493:pharmacokinetics; D011162:Porphobilinogen / Q000031:analogs & derivatives* / Q000737:chemistry / Q000493:pharmacokinetics; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D001372:Aza Compounds; D005456:Fluorescent Dyes; D008301:Maleimides; D010456:Peptides, Cyclic; D013438:Sulfhydryl Compounds; C507169:cyclic arginine-glycine-aspartic acid peptide; C507544:dipyrromethene; C043592:maleimide; D011162:Porphobilinogen; D005978:Glutathione