Synthesis and Liposome Insertion of a New Poly(carboranylalkylthio)porphyrazine to Improve Potentiality in Multiple-Approach Cancer Therapy

Abstract

Liposome insertion of a newly synthesized octa-carboranylhexylthio-porphyrazine (H2HECASPz) with potentiality in anticancer multiple therapy was described at molecular and supramolecular level. Host−guest interactions between H2HECASPz and the liposome constituents were established and were confirmed by DFT calculations. An approach for the design of new porphyrin-like molecules to be carried by liposome is presented

Boron-Containing Phthalocyanines and Porphyrazines

“…[53][54][55][56] The synthesized highly hydrophobic porphyrazines were solubilized via loading into liposomes of different types and physicochemical properties of these lipids were studied. [54][55][56][57] To enchance water-solubility of the prepared porphyrazines the closo-carborane groups can be converted to the nido-carborane ones by the treatment with CsF followed by the Cs/K exchange to give the corresponding water-soluble boronated porphyrazines (Scheme 14). [53] More recently synthesis of the highly boronated porphyrazine 25 containing sixteen carborane fragments has been reported (Scheme 15).…”

Carboranylporphyrazines for anti-cancer therapies: synthesis and physicochemical properties

“…Both MgMCHESPz and H 2 MCHESPz gave more than satisfactory characterization data. It is worthwhile to point out that H 2 MCHESPz, just as the H 2 ACHESPz analog, exhibits a strong Q band at 712 nm (ε ~ 2.8 × 10 4 M -1 cm -1 ), with extremely weak fluorescence (φ F ~ 10 -4 ) and rapid -in the picosecond regime -radiationless decay of the photogenerated S 1 (Q) excited state [43]. Again, we have a case of tetrapyrrolic macrocycle for which the S 1 (Q) state decays non-radiatively even in the absence of a quenching coordinated metal.…”

“…Specifically, the loaded vectors were characterized by Dynamic Light Scattering (DLS), Zeta potential (ζ), Small Angle Neutron Scattering (SANS) and Synchrotron Small Angle X-Ray Scattering (SAXS), whereas valuable information on the host-guest interactions at molecular level were obtained by Density Functional Theory (DFT) calculations [43][44][45].…”

“…In the past three years, we focused on the porphyrazine (Pz) macrocycle -a small-ring tetrapyrrole relatively less studied than the porphyrin analog -as a potential carrier of highly boronated chemical functions [40][41][42][43][44][45]. Our aim was to design and synthesize Pzs bearing carboranylcontaining pendants, to deliver into cancerous cells, preferably with the help of liposomal vectors.…”

“…Several neutral and anionic o-carboranylporphyrazines have been synthesized in our laboratory [40][41][42][43][44][45]56]. In these nanosized molecules the C(1) atom of the o-carborane cage is linked to the Pz ring through a hexylthio-tail, whereas the C(2) atom bears ad hoc bonded chemical functions.…”