Structurally Characterized BODIPY-Appended Oxidovanadium(IV) β‑Diketonates
for Mitochondria-Targeted Photocytotoxicity
Posted on 2020-02-24 - 13:49
Mixed-ligand
oxidovanadium(IV) β-diketonates having NNN-donor dipicolylamine-conjugated
to boron-dipyrromethene (BODIPY in L1) and diiodo-BODIPY
(in L2) moieties, namely, [VO(L1)(acac)]Cl (1), [VO(L2)(acac)]Cl (2), and [VO(L1)(dbm)]Cl (3), 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 1 and 2 were
structurally characterized as their PF6– salts (1a and 2a) by X-ray crystallography.
They showed VIVN3O3 six-coordinate
geometry with dipicolylamine base as the facial ligand. The non-iodinated
BODIPY complexes displayed absorption maxima at ∼501 nm, while
it is ∼535 nm for the di-iodinated 2 in 10% DMSO–PBS
buffer medium (pH = 7.2). Complexes 1 and 3 being green emissive (λem, ∼512 nm; λex, 470 nm; ΦF, ∼0.10) in 10% aqueous
DMSO were used for cellular imaging studies. Complex 3 localized primarily in the mitochondria of the cervical HeLa cells
with a co-localization coefficient value of 0.7. The non-emissive
diiodo-BODIPY complex 2 showed generation of singlet
oxygen (ΦΔ ≈ 0.47) on light activation.
Annexin-V assay showed singlet oxygen-mediated cellular apoptosis,
making this complex a targeted PDT agent.
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Bhattacharyya, Utso; Verma, Brijesh K.; Saha, Rupak; Mukherjee, Nandini; Raza, Md Kausar; Sahoo, Somarupa; et al. (2020). Structurally Characterized BODIPY-Appended Oxidovanadium(IV) β‑Diketonates
for Mitochondria-Targeted Photocytotoxicity. ACS Publications. Collection. https://doi.org/10.1021/acsomega.9b04204
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AUTHORS (8)
UB
Utso Bhattacharyya
BV
Brijesh K. Verma
RS
Rupak Saha
NM
Nandini Mukherjee
MR
Md Kausar Raza
SS
Somarupa Sahoo
PK
Paturu Kondaiah
AC
Akhil R. Chakravarty
KEYWORDS
dbmComplexes 1PDT agentΦ Fabsorption maximaphotoinduced anticancer activityNNN-donor dipicolylamine-conjugatedL 2L 1acacimaging studiesPFVOsinglet oxygen-mediatedComplex 3non-iodinated BODIPY complexesco-localization coefficient value470 nmAnnexin-V assaynon-emissive diiodo-BODIPYlight activationX-ray crystallographyV IV N 3 O 3 six-coordinate geometrydipicolylamine baseHeLa cellsdi-iodinated 2DMSO