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Recent strategies to improve boron dipyrromethene (BODIPY) for photodynamic cancer therapy: an updated review

Published on Jan 1, 2018in Photochemical and Photobiological Sciences2.408
· DOI :10.1039/C8PP00113H
Chin Siang Kue4
Estimated H-index: 4
(Management and Science University),
Shie Yin Ng2
Estimated H-index: 2
(UM: University of Malaya)
+ 4 AuthorsHong Boon Lee7
Estimated H-index: 7
(UM: University of Malaya)
Abstract
BODIPYs are photosensitizers activatable by light to generate highly reactive singlet oxygen (1O2) from molecular oxygen, leading to tissue damage in the photoirradiated region. Despite their extraordinary photophysical characteristics, they are not featured in clinical photodynamic therapy. This review discusses the recent advances in the design and/or modifications of BODIPYs since 2013, to improve their potential in photodynamic cancer therapy and related areas.
  • References (62)
  • Citations (16)
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References62
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#1Dapeng ChenH-Index: 5
#2Qianyun TangH-Index: 11
Last. Xiaochen DongH-Index: 29
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Synergistic cancer therapy is of great interest for multiple advantages, such as excellent targeting accuracy, low side effects, and enhanced therapeutic efficiency. Herein, a near-infrared photosensitizer aza-BODIPY (AB) with high singlet oxygen quantum yield (ΦΔ = 82%) is designed and synthesized. With Schiff's base obtained from condensation reaction between doxorubicin (DOX) and polyethylene glycol-benzaldehyde (PEG-CHO) as the polymer matrix, aza-BODIPY is encapsulated to afford hydrophilic...
26 CitationsSource
#1Yang Liu (Northeast Normal University)H-Index: 6
#2Nan Song (Northeast Normal University)H-Index: 5
Last. Zhigang Xie (CAS: Chinese Academy of Sciences)H-Index: 44
view all 4 authors...
We present a new cyclometalated Ir(III) complexes IrBDP, which could self-assemble into organic nanoparticles (IrBDP NPs). IrBDP NPs show enhanced photodynamic effect and can be engulfed by HeLa cells for cell imaging as well as photodynamic therapy (PDT) upon low energy irradiation.
6 CitationsSource
#1Ilke Simsek Turan (Bilkent University)H-Index: 9
#2Gurcan Gunaydin (Hacettepe University)H-Index: 4
Last. Engin U. Akkaya (Bilkent University)H-Index: 53
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Molecular logic gates are expected to play an important role on the way to information processing therapeutic agents, especially considering the wide variety of physical and chemical responses that they can elicit in response to the inputs applied. Here, we show that a 1:2 demultiplexer based on a Zn2+-terpyridine-Bodipy conjugate with a quenched fluorescent emission, is efficient in photosensitized singlet oxygen generation as inferred from trap compound experiments and cell culture data. Howev...
17 CitationsSource
#1Nandini Mukherjee (IISc: Indian Institute of Science)H-Index: 2
#2Santosh Podder (IISc: Indian Institute of Science)H-Index: 3
Last. Akhil R. Chakravarty (IISc: Indian Institute of Science)H-Index: 53
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Copper(II) complexes [Cu(L1/L2/L3)(A)] (1–3), where H2A·HCl is a vitamin B6 Schiff base, viz. 3-hydroxy-5-(hydroxymethyl)-4-(((2-hydroxyphenyl)imino)methyl)-2-methylpyridin-1-ium chloride, L1 and L2 are 2-(2-pyridyl)benzimidazole based borondipyrromethene (BODIPY) ligands and L3 is 2-(2-pyridyl)benzimidazole, were prepared, characterized and their visible light-induced anti-cancer activity was studied. Complex 3, characterized by X-ray crystallography, exhibits a distorted square-pyramidal geome...
11 CitationsSource
#1Mingle Li (DUT: Dalian University of Technology)H-Index: 6
#2Ruisong Tian (DUT: Dalian University of Technology)H-Index: 3
Last. Xiaojun Peng (DUT: Dalian University of Technology)H-Index: 57
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Abstract As an indispensable organelle, lysosomes play critical role in cell digestion and are closely relate to cell death and apoptosis. Photosensitizers that target to lysosomes are extremely important to photodynamic therapy. Herein, we report an excellent BODIPY based photosensitizer MBDP for lysosome targeting NIR photosensitizer. MBDP exhibits excellent PDT efficiency with low IC50 of 0.2 μM compared to the classical photosensitizer Ce6 (IC50 = 1.39 μM). Furthermore, MBDP can localize in ...
21 CitationsSource
#1Utso BhattacharyyaH-Index: 1
#2Brijesh KumarH-Index: 1
Last. Akhil R. ChakravartyH-Index: 53
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Ternary oxidovanadium(IV) complexes of curcumin (Hcur), dipicolylamine (dpa) base, and its derivatives having pendant noniodinated and di-iodinated boron-dipyrromethene (BODIPY) moiety (L1 and L2, respectively), namely, [VO(dpa)(cur)]ClO4 (1), [VO(L1)(cur)]ClO4 (2), and [VO(L2)(cur)]ClO4 (3) and their chloride salts (1a–3a) were prepared, characterized, and studied for anticancer activity. The chloride salts were used for biological studies due to their aqueous solubility. Complex 1 was structur...
12 CitationsSource
#1Quan Zhang (Jiangnan University)H-Index: 3
#2Ying Cai (Jiangnan University)H-Index: 2
Last. Jian Yin (Jiangnan University)H-Index: 7
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The targeted delivery of a photosensitizer (PS) with appropriate carriers represents an attractive means of selectively delivering cargo to target tissues or subcellular compartments for photodynamic therapy (PDT). Herein, a three-arm distyryl BODIPY derivative conjugated with mannose units (denoted by BTM) that can co-assemble with Tween 80 to form nanomicelles (BTM-NMs) for targeted PDT is reported. MDA-MB-231 breast cancer cells recognized and specifically internalized BTM-NMs via mannose-rec...
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#1Jianhua ZouH-Index: 8
#2Zhihui YinH-Index: 5
Last. Xiaochen DongH-Index: 29
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Heavy atom effect and configuration are important for BODIPY derivatives to generate singlet oxygen (1O2) for photodynamic therapy. Herein, a series of BODIPY derivatives with different halogens were synthesized. 1O2 quantum yields (QYs) and MTT assay confirm that incorporation of more heavy atoms onto dimeric BODIPY cannot effectively enhance the 1O2 QYs. Rather, the dark toxicity increases. This phenomenon can be attributed to the competition of heavy atom effect and configuration of dimeric B...
34 CitationsSource
#1Xian-Fu Zhang (Hebei Normal University of Science and Technology)H-Index: 1
#2Nan Feng (Hebei Normal University of Science and Technology)H-Index: 1
Pristine BODIPY compounds have negligible efficiency to generate excited triplet state and singlet oxygen. In this report we show that attaching a good electron donor to BODIPY core can lead to the singlet oxygen formation up to 58% quantum efficiency. For this purpose, BODIPYs with meso-aryl (phenyl, naphthyl, anthryl, and pyrenyl) were synthesized and characterized. The fluorescence, excited triplet state and singlet oxygen formation properties for these compounds were measured in various solv...
12 CitationsSource
#1Kausar RazaH-Index: 3
#2Srishti GautamH-Index: 5
Last. Akhil R. ChakravartyH-Index: 53
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Monofunctional platinum(II) complexes of formulation cis-[Pt(NH3)2(L)Cl](NO3), where L is an imidazole base conjugated to 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) with emissive (L1 in 1) and nonemissive (L2 in 2) moieties were prepared and characterized, and their singlet oxygen-mediated photoinduced cytotoxicity was studied. The 1-methylimidazole (1-MeIm) complex 3 was prepared as a control and for structural characterization by X-ray crystallography. Complexes 1 and 2 showed strong ...
16 CitationsSource
Cited By16
Newest
#1Hasrat Ali (Université de Sherbrooke)H-Index: 25
#2Brigitte Guérin (Université de Sherbrooke)H-Index: 24
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Abstract A series of BODIPYs (boron-dipyrromethene dyes; 4,4-difluoro-5-aryl-4-bora-3a, 4a-diaza-s-indacene) derivatives, bearing an aldehyde group at different pyrrole positions, were transformed into gem-dibromovinyl analogs using the Corey-Fuchs or Lautens olefination method. The gem-dibromovinyl moieties (one or two) are symmetric/asymmetric and attached at α- or β-positions of the pyrrole ring, directly or through the extension of a β-position substituted phenyl spacer ring. The molecular s...
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#1Jaroslaw Piskorz (Poznan University of Medical Sciences)H-Index: 9
#2Jolanta Dlugaszewska (Poznan University of Medical Sciences)H-Index: 6
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Abstract Novel boron-dipyrromethene derivatives with N-alkyl phthalimide and amine substituents, including iodinated derivative, were synthesized and characterized using UV–Vis spectrophotometry, mass spectrometry (HRMS) and NMR spectroscopy. Non-iodinated analogs revealed high emission properties with fluorescence quantum yields (ΦF) between 0.48 and 0.58. But singlet oxygen generation quantum yields (ΦΔ) were low with values in the range of 0.01–0.06. Iodinated derivative revealed a strong hea...
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#2Justin C. Johnson (NREL: National Renewable Energy Laboratory)H-Index: 37
Last. Praveen C. Ramamurthy (IISc: Indian Institute of Science)H-Index: 21
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Abstract Two pairs of A-D-A molecules have been synthesized with fluorene and benzodithiophene as the central donor subunits and terminal BODIPY units, functionalized with either a 4-methylphenyl or 4-trifluoromethylphenyl group at the meso position. The effect of the para substituent of the meso phenyl group on the photophysical properties of these molecules is studied through steady state absorption and fluorescence spectroscopy as well as femtosecond transient absorption and time resolved flu...
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Abstract Monostyryl and distyryl substituted BODIPY derivatives were synthesized by the Knoevenagel condensation reaction and fully characterized by 1H NMR and HRMS. Their photophysical and electrochemical properties have been investigated by UV–vis absorption spectroscopy, steady-state and time-resolved fluorescence spectroscopy, two-photon excited spectroscopy and cyclic voltammetry. These BODIPY dyes exhibit excellent photophysical properties in red to near-infrared region, including large ex...
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Intramolecular rotations are known to interfere with the excited-state processes resulting in luminescence quenching. Efforts aimed at restricting intramolecular rotations have led to the development of highly luminescent systems. Here we report the luminescence properties of a BODIPY molecule (I6) containing six iodo-substituents. The luminescence of I6 was highly quenched in the solution state whereas the conversion of this molecule into its nanoaggregates enhanced the emission intensity. Deta...
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Abstract Asymmetric meso-CF3-dipyrromethanes with amino- and nitrogen heterocyclic functions, a new family of the BODIPY dye precursors, have been synthesized in 70-90% yield by condensation of trifluoro(pyrrolyl)ethanols with pyrroles in the presence of AlCl3. This catalyst, for the first time, was shown to be more efficient than commonly used P2O5, which was entirely inactive in the condensation of pyrroles having basic substituents (amino group and pyrazole moiety).
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A strategy to create organic molecules with high degrees of radical spin multiplicity is reported in which molecular design is correlated with the behaviour of radical anions in a series of BODIPY dyads. Upon reduction of each BODIPY moiety radical anions are formed which are shown to have different spin multiplicities by electron paramagnetic resonance (EPR) spectroscopy and distinct profiles in their cyclic voltammograms and UV-visible spectra. The relationship between structure and multiplici...
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Organic photosensitizers possessing efficient intersystem crossing (ISC) and forming long-living triplet excited states, play a crucial role in a number of applications. A common approach in the design of such dyes relies on the introduction of heavy atoms (e.g. transition metals or halogens) into the structure, which promote ISC via spin–orbit coupling interaction. In recent years, alternative methods to enhance ISC have been actively studied. Among those, the generation of triplet excited stat...
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We prepared amide-heterocycle (HC) compounds having various aromatic π-electron systems (Ar), such as phenyl, naphthyl, furyl, thienyl and phenanthryl moieties, and converted them as ligands to difluoroboronated complexes, Ar@HCs. Blue fluorescence from Ar@HCs was observed in solution and the solid state, and the fluorescence quantum yields (Φf) and lifetimes (τf) were determined. The Φf values in CHCl3 were as small as 0.1 except for the phenanthrene derivatives (0.4–0.6). Observation of the tr...
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#1Ewen Bodio (University of Burgundy)H-Index: 12
#2Franck Denat (University of Burgundy)H-Index: 24
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Since their discovery in 1968, the BODIPYs dyes (4,4-difluoro-4-bora-3a, 4a diaza-s-indacene) have found an exponentially increasing number of applications in a large variety of scientific fields. ...
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