Biotin-Pt(IV)-Ru(II)-Boron-Dipyrromethene Prodrug as "Platin Bullet" for Targeted Chemo- and Photodynamic Therapy.

Using the principle of "Magic Bullet", a cisplatin-derived platinum(IV) prodrug heterobimetallic complex, -[Pt(NH)Cl{Ru(tpy-BODIPY)(tpy-COO)}(biotin)]Cl (, ), having two axial ligands, namely, biotin as water-soluble B-vitamin for enhanced cellular uptake and a BODIPY-ruthenium(II) (, ) photosensitizer having ,,-donor tpy (4'-phenyl-2,2':6',2″-terpyridine) bonded to boron-dipyrromethene (BODIPY), is developed as a "Platin Bullet" for targeted photodynamic therapy (PDT). exhibited intense absorption near 500 nm and emission near 513 nm (λ = 488 nm) in a 10% dimethyl sulfoxide-Dulbecco's phosphate-buffered saline medium (pH 7.2).

Photodynamic Therapy with Targeted Release of Boron-Dipyrromethene Dye from Cobalt(III) Prodrugs in Red Light.

Boron-dipyrromethene (BODIPY) dyes are promising photosensitizers for cellular imaging and photodynamic therapy (PDT) owing to their excellent photophysical properties and the synthetically tunable core. Metalation provides a convenient way to overcome the drawbacks arising from their low aqueous solubility. New photo-/redox-responsive Co(III) prodrug chaperones are developed as anticancer PDT agents for efficient cellular delivery of red-light-active BODIPY dyes.

A Platinum(II) Boron-dipyrromethene Complex for Cellular Imaging and Mitochondria-targeted Photodynamic Therapy in Red Light.

Cisplatin-derived platinum(II) complexes [Pt(NH ) (pacac)](NO ) (1, DPP-Pt) and [Pt(NH ) (Acac-RB)](NO ) (2, Acacplatin-RB), where Hpacac is 1,3-diphenyl-1,3-propanedione and HAcac-RB is a red-light active distyryl-BODIPY-appended acetylacetone ligand, are prepared, characterized and their photodynamic therapy (PDT) activity studied (RB abbreviated for red-light BODIPY). Complex 2 displayed an intense absorption band at λ=652 nm (ϵ=7.3×10  M  cm ) and 601 nm (ϵ=3.

Biotin and boron-dipyrromethene-tagged platinum(IV) prodrug for cellular imaging and mito-targeted photocytotoxicity in red light.

A platinum(IV) prodrug, ,,-[Pt(NH)Cl(biotin)(L)] (1), derived from cisplatin, where HL is the PEGylated red-light active boron-dipyrromethene (BODIPY) ligand, was synthesized, characterized and its photocytotoxicity evaluated. The complex showed a near-IR absorption band at 653 nm ( ∼9.19 × 10 M cm) in dimethyl sulfoxide and Dulbecco's phosphate-buffered saline (1 : 1 v/v) at pH 7.

Lysosome directed red light photodynamic therapy using glycosylated iron-(III) conjugates of boron-dipyrromethene.

To overcome the drawbacks associated with chemotherapeutic and porphyrin-based photodynamic therapy (PDT) agents, the use of BODIPY (boron-dipyrromethene) scaffold has gained prominence in designing a new generation of photosensitizers-cum-cellular imaging agents. However, their poor cell permeability and limited solubility in aqueous medium inhibits the in-vitro application of their organic form. This necessitates the development of metal-BODIPY conjugates with improved physiological stability and enhanced therapeutic efficacy.

Bichromophoric ruthenium(II) bis-terpyridine-BODIPY based photosensitizers for cellular imaging and photodynamic therapy.

Two multichromophoric homoleptic ruthenium(II) complexes [Ru(tpy-BODIPY)]Cl (complexes 1 and 2, tpy = 4-phenyl-2,2:6,2-terpyridine, BODIPY = boron-dipyrromethene) were prepared, characterized and their phototherapeutic activity and bioimaging properties were studied. The complexes having structural similarity differ only by a phenylethynyl linker, and its overall influence on their physicochemical and photobiological behavior was evaluated. The terpyridine-BODIPY ligand L was structurally characterized by X-ray crystallography.

Cobalt(III) Complexes for Light-Activated Delivery of Acetylacetonate-BODIPY, Cellular Imaging, and Photodynamic Therapy.

Cobalt(III) complexes [Co(TPA)(L)](ClO) (), [Co(4-COOH-TPA)(L)](ClO) (), [Co(TPA)(L)]Cl (), and [Co(4-COOH-TPA)(L)]Cl () having acetylacetonate-linked boron-dipyrromethene ligands (, acac-BODIPY; , acac-diiodo-BODIPY) were prepared and characterized, and their utility as bioimaging and phototherapeutic agents was evaluated (TPA, tris-(2-pyridylmethyl)amine; 4-COOH-TPA, 2-((bis-(2-pyridylmethyl)amino)methyl)isonicotinic acid). , , and complex were structurally characterized by X-ray crystallography. Complexes and on photoactivation or in a reducing environment (excess GSH, ascorbic acid, and 3-mercaptopropionic acid) released the acac-BODIPY ligand.

BODIPY-dipicolylamine complexes of platinum(II): X-ray structure, cellular imaging and organelle-specific near-IR light type-II PDT.

Dipicolylamine (dpa) based platinum(II) complexes [Pt(L1-3)Cl]Cl (1-3), where L2 and L3 are green and red light BODIPY-tagged dpa ligands and L1 is a benzyl derivative of dpa, were synthesized and characterized and their cytotoxicity was studied. The perchlorate salt of complex 2 was structurally characterized. It showed a PtNCl core with a deformed square-planar geometry.

BODIPY-Tagged Platinum(II) Curcumin Complexes for Endoplasmic Reticulum-Targeted Red Light PDT.

[Pt(RB)(Cur)]NO (), [Pt(IRB)(Cur)]NO (), and [Pt(L)(Cur)]NO (), where HCur is curcumin, L is 1-benzyl-2-(2-pyridyl)benzimidazole, and RB and IRB are red-light-active non-iodo and diiodo-BODIPY tagged to L, respectively, were synthesized and characterized, and their anticancer activities were studied (BODIPY, boron-dipyrromethene). and displayed BODIPY-centered absorption bands within 615-635 nm along with the respective curcumin bands at 445 and 492 nm in 10% dimethyl sulfoxide (DMSO)-Dulbecco's phosphate-buffered saline (DPBS). Emission bands were observed at 723 and 845 nm for and , respectively, in 10% DMSO-DPBS.

BODIPY-Ruthenium(II) Bis-Terpyridine Complexes for Cellular Imaging and Type-I/-II Photodynamic Therapy.

A series of multichromophoric ruthenium(II) complexes with the formulation [Ru(tpy-BODIPY)(tpy-R)]Cl (-), having a heteroleptic Ru(II)-bis-tpy (tpy = 4'-phenyl-2,2':6',2″-terpyridine) moiety covalently linked to a boron-dipyrromethene (BODIPY) pendant, have been prepared and characterized and their application as a phototherapeutic and photodetection agent in cancer therapy has been explored. Ligand L with a terpyridine-BODIPY moiety and complex as its PF salt () have been structurally characterized by a single-crystal X-ray diffraction study. Complex has a distorted-octahedral RuN core with a Ru(II)-bis-terpyridine unit that is covalently linked to one photoactive BODIPY unit.

Oxoplatin-B, a cisplatin-based platinum(IV) complex with photoactive BODIPY for mitochondria specific "chemo-PDT" activity.

Oxoplatin-B, a platinum(IV) complex [Pt(NH)Cl(L)(OH)] (1) of 4-methylbenzoic acid (HL) functionalized with 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) was prepared, characterized and its antitumor activity studied. [Pt(NH)Cl(L)(OH)] (2) of 4-methylbenzoic acid (HL) was studied as a control. Complex 1 showed an absorption band at 500 nm (ɛ = 4.

BODIPY-attached zinc(II) complexes of curcumin drug for visible light assisted photo-sensitization, cellular imaging and targeted PDT.

Boron-dipyrromethene (BODIPY) based photosensitizers as porphyrinoids and curcumin as natural product possess exciting photophysical features suitable for theranostic applications, namely, imaging and photodynamic therapy (PDT). Limited aqueous solubility and insufficient physiological stability, however, reduce their efficacy significantly. We have designed a novel strategy to deliver these two unusable cytotoxins simultaneously in cancer cells and herein, report the synthesis, characterization and imaging-assisted photocytotoxicity of three zinc(II) complexes containing N-donor dipicolylamine (dpa) ligands (L) and O,O-donor curcumin (Hcur) viz.

Maloplatin-B, a Cisplatin-Based BODIPY-Tagged Mito-Specific "Chemo-PDT" Agent Active in Red Light.

Maloplatin-B, a cisplatin-based complex, namely [Pt()(NH)](NO) () with a pendant boron-dipyrromethene (BODIPY) moiety, where H is a methyl malonyl chloride derived monostyryl BODIPY ligand, was designed and developed as near-IR light (600-720 nm) organelle-targeting photodynamic therapy agent. The complex [Pt(acac)(NH)](NO) () was used as a control. displayed an absorption band at 616 nm (ε = 2.

BODIPY-linked cis-dichlorido zinc(ii) conjugates: the strategic design of organelle-specific next-generation theranostic photosensitizers.

Dipicolylamine (dpa) based cis-dichlorido zinc(ii) complexes [Zn(L)Cl] (1-3), where L and L are non-iodo and di-iodo BODIPY-appended dpa in 2 and 3, and L is dpa in control complex 1, were prepared and characterized and their photocytotoxicity was studied. Complexes 2 and 3 were developed as potential substitutes for zinc(ii)-porphyrins/phthalocyanines that are photodynamic therapeutic agents with moderate activity owing to their inherent hydrophobicity and aggregation-induced deactivation mechanism. In our approach, we strategically designed hybrid inorganic-organic zinc-BODIPY conjugates as theranostic photosensitizers.

Structurally Characterized BODIPY-Appended Oxidovanadium(IV) β-Diketonates for Mitochondria-Targeted Photocytotoxicity.

Mixed-ligand oxidovanadium(IV) β-diketonates having NNN-donor dipicolylamine-conjugated to boron-dipyrromethene (BODIPY in L) and diiodo-BODIPY (in L) moieties, namely, [VO(L)(acac)]Cl (), [VO(L)(acac)]Cl (), and [VO(L)(dbm)]Cl (), where acac and dbm are monoanionic O,O-donor acetylacetone and 1,3-diphenyl-1,3-propanedione, were prepared, characterized, and tested for their photoinduced anticancer activity in visible light. Complexes and were structurally characterized as their PF salts ( and ) by X-ray crystallography. They showed VNO six-coordinate geometry with dipicolylamine base as the facial ligand.

Ruthenium(II) Conjugates of Boron-Dipyrromethene and Biotin for Targeted Photodynamic Therapy in Red Light.

The ruthenium(II) complexes [RuCl(L)(L)]Cl (), [RuCl(L)(L)]Cl (), [RuCl(L)(L)]Cl (), [RuCl(L)(L)]Cl (), and [RuCl(L)(L)]Cl () of NNN-donor dipicolylamine (dpa) bases (L, L) having BODIPY (boron-dipyrromethene) moieties, NN-donor phenanthroline derivatives (L, L), and benzyldipicolylamine (bzdpa, L) were prepared and characterized by spectroscopic techniques and their cellular localization/uptake and photocytotoxicity studied. Complex , as its PF salt (), has been structurally characterized with help of a single-crystal X-ray diffraction technique. It has a RuNCl core with the Cl bonded trans to the amine nitrogen atom of bzdpa.

Crystal structure, DNA crosslinking and photo-induced cytotoxicity of oxovanadium(IV) conjugates of boron-dipyrromethene.

Cis-dichloro-oxovanadium(IV) complexes [VO(L/L)Cl], where L is N-(4-(5,5-difluoro-1,3,7,9-tetramethyl-5H-4ʎ,5ʎ-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-10-yl)benzyl)-1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)methanamine in 1 and L is N-(4-(5,5-difluoro-2,8-diiodo-1,3,7,9-tetramethyl-5H-4ʎ,5ʎ-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-10-yl)benzyl)-1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)methanamine in 2) having 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene as boron-dipyrromethene (BODIPY) appended dipicolylamine bases were prepared, characterized and their photocytotoxicity studied. X-ray crystal structure of 1 showed distorted octahedral geometry with a VONCl core having Cl-V-Cl angle of 91.93(4)°.

Correction: Impact of metal binding on the antitumor activity and cellular imaging of a metal chelator cationic imidazopyridine derivative.

Correction for 'Impact of metal binding on the antitumor activity and cellular imaging of a metal chelator cationic imidazopyridine derivative' by Mithun Roy et al., Dalton Trans., 2011, 40, 4855-4864.

Correction: Endoplasmic reticulum targeting tumour selective photocytotoxic oxovanadium(iv) complexes having vitamin-B6 and acridinyl moieties.

Correction for 'Endoplasmic reticulum targeting tumour selective photocytotoxic oxovanadium(iv) complexes having vitamin-B6 and acridinyl moieties' by Samya Banerjee et al., Dalton Trans., 2016, 45, 783-796.

Correction: Endoplasmic reticulum targeted chemotherapeutics: the remarkable photo-cytotoxicity of an oxovanadium(iv) vitamin-B6 complex in visible light.

Correction for 'Endoplasmic reticulum targeted chemotherapeutics: the remarkable photo-cytotoxicity of an oxovanadium(iv) vitamin-B6 complex in visible light' by Samya Banerjee et al., Chem. Commun.