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Synthesis and physico-chemical properties of a H-cardanol triazole zinc porphyrin conjugate.

ABSTRACT: Although a large number of natural and non-natural metalloporphyrins are known, examples with fluorescence and fat-soluble properties are rare. We have achieved the synthesis of a fluorescent and fat-soluble zinc porphyrin incorporating four units of hydrogenated cardanol (H-cardanol). The synthesis is sustainable since the product is derived from cashew-nut shell liquid (CNSL), which is a renewable and bio-waste material. The H-cardanol triazole zinc porphyrin conjugate (HTZPC) was synthesized through applying a copper(i) catalyzed azide-alkyne cycloaddition (CuAAC) reaction between a H-cardanol derived azide and a tetraarylporphyrin derived alkyne. The absorption and emission properties of the hydrocarbon solvent soluble HTZPC were evaluated using UV-vis and fluorescence emission spectra obtained in various solvents. The results were compared with related molecules like a triazole-zinc porphyrin conjugate (TZPC), zinc tetra-C(4)-methoxyphenyl porphyrin (ZP), and a H-cardanol-triazole conjugate (HTC). The results showed that HTZPC undergoes J-type aggregation in both non-polar and highly polar solvents, which is dictated by van der Waals attractive forces between H-cardanol units in polar solvents (e.g. methanol and dimethylformamide) and π-π stacking interactions between porphyrin units in non-polar solvents (hexane). Moreover, the spectra indicated that the triazole units could stabilize the zinc porphyrin via intermolecular coordinate-complex formation. We anticipate that fat-soluble HTZPC could find applications in medical fields (e.g. in the photodynamic therapy of fat tissue).

SUBMITTER: Prakash Rao HS

PROVIDER: S-EPMC9060588 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Synthesis and physico-chemical properties of a H-cardanol triazole zinc porphyrin conjugate.

Prakash Rao H Surya HS Kamalraj M M Prabakaran M M

RSC advances 20190101 8

Although a large number of natural and non-natural metalloporphyrins are known, examples with fluorescence and fat-soluble properties are rare. We have achieved the synthesis of a fluorescent and fat-soluble zinc porphyrin incorporating four units of hydrogenated cardanol (H-cardanol). The synthesis is sustainable since the product is derived from cashew-nut shell liquid (CNSL), which is a renewable and bio-waste material. The H-cardanol triazole zinc porphyrin conjugate (HTZPC) was synthesized ...[more]

PMID: 35520169

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Project description:Oligonucleotide conjugates with boron clusters have found applications in different fields of molecular biology, biotechnology, and biomedicine as potential agents for boron neutron capture therapy, siRNA components, and antisense agents. Particularly, the closo-dodecaborate anion represents a high-boron-containing residue with remarkable chemical stability and low toxicity, and is suitable for the engineering of different constructs for biomedicine and molecular biology. In the present work, we synthesized novel oligonucleotide conjugates of closo-dodecaborate attached to the 5'-, 3'-, or both terminal positions of DNA, RNA, 2'-O-Me RNA, and 2'-F-Py RNA oligomers. For their synthesis, we employed click reaction with the azido derivative of closo-dodecaborate. The key physicochemical characteristics of the conjugates have been investigated using high-performance liquid chromatography, gel electrophoresis, UV thermal melting, and circular dichroism spectroscopy. Incorporation of closo-dodecaborate residues at the 3'-end of all oligomers stabilized their complementary complexes, whereas analogous 5'-modification decreased duplex stability. Two boron clusters attached to the opposite ends of the oligomer only slightly influence the stability of complementary complexes of RNA oligonucleotide and its 2'-O-methyl and 2'-fluoro analogs. On the contrary, the same modification of DNA oligonucleotides significantly destabilized the DNA/DNA duplex but gave a strong stabilization of the duplex with an RNA target. According to circular dichroism spectroscopy results, two terminal closo-dodecaborate residues cause a prominent structural rearrangement of complementary complexes with a substantial shift from the B-form to the A-form of the double helix. The revealed changes of key characteristics of oligonucleotides caused by incorporation of terminal boron clusters, such as the increase of hydrophobicity, change of duplex stability, and prominent structural changes for DNA conjugates, should be taken into account for the development of antisense oligonucleotides, siRNAs, or aptamers bearing boron clusters. These features may also be used for engineering of developing NA constructs with pre-defined properties.

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Synthesis and physico-chemical properties of a H-cardanol triazole zinc porphyrin conjugate.

Publications

Synthesis and physico-chemical properties of a H-cardanol triazole zinc porphyrin conjugate.

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