Mitochondria selective trackers for long-term imaging based on readily accessible neutral BODIPYs

Abstract

We report the design of a new model based on a small neutral 8-aryl-3-formylBODIPY and its suitability to develop privileged highly-bright and photostable fluorescent probes for selective and, more important,...

Mitochondrial Targeting and Imaging with Small Organic Conjugated Fluorophores: A Review

“…An interesting set of structural analogues were reported (37--41), where small substitutions were observed to dramatically dictate the accumulation in the mitochondria. [61] In short, for systems bearing meso benzyl chloride substitution (37 and 38), mitochondrial accumulation was only observed when a formyl Chemistry-A European Journal…”

“…However, successful attempts on this regard have been reported exploiting BODIPY chemistries. An interesting set of structural analogues were reported ( 37‐ ‐ 41 ), where small substitutions were observed to dramatically dictate the accumulation in the mitochondria [61] . In short, for systems bearing meso benzyl chloride substitution ( 37 and 38 ), mitochondrial accumulation was only observed when a formyl moiety is present on position 6 ( 37 ) and not on 5 ( 38 ), at the expense of a significant decrease in quantum efficiency (φ f =0.02 and 0.40 for 37 and 38 in DMSO, respectively).…”

“…Synthetically, the way this class of materials is afforded is dictated by the overall symmetry of the molecule. Symmetric systems[ 34 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 ] can be accessed by reaction of the desired substituted pyrrole with an aldehyde or an acid chloride/anhydride. [ 68 , 69 , 70 , 71 , 72 ] In both cases, the first synthetic step is the generation of the relevant dipyrromethene intermediate.…”

Balizko molekula fotoaktibo multifuntzionala biomedikuntzarako

“…Behar hori asetzeko asmoz, BODIPY koloratzailea berriz ere hautagai aproposa da. Mitokondrien detekzioa ahalbidetzeko formilo taldea txertatu da kromoforoaren 3 posizioan (6. irudia) [31]. Egitura-aldaketa sinple hori gai da BODIPYaren eta organuluan dauden proteinen amino taldeen arteko erreakzioa bultzatzeko, eta bide batez hori tindatzeko zunda fluoreszente neutro bat erabiliz, potentzial elektrikoan inongo eraginik izan barik.…”

“…Egitura-aldaketa sinple hori gai da BODIPYaren eta organuluan dauden proteinen amino taldeen arteko erreakzioa bultzatzeko, eta bide batez hori tindatzeko zunda fluoreszente neutro bat erabiliz, potentzial elektrikoan inongo eraginik izan barik. Mitokondriak tindatzeko ahalmena egiaztatzeko in vitro saioak egin ziren PC-3 prostata minbizi zelula erabiliz eta irudi fluoreszenteak lortu ziren mikroskopio konfokalaren bidez (6. irudia) [31]. Formilodun BODIPYa zeluletan barneratzen da (2 minututan) eta mitokondrietan oso azkar (5 minutu igarota) metatzen dela ikus daiteke.…”