Icosahedral boron clusters as modifying entities for biomolecules

Abstract

Icosahedral boron clusters have unique properties useful in medicinal chemistry: rigidity, chemical stability, and three-dimensional aromaticity. Furthermore, these abiotic compounds have low toxicity and are stable in the biological environment. All these features ultimately give them the ability to interact with biological molecules in a different mode than organic compounds. Areas covered: In the present article, we aim to introduce boron clusters as a class of entities suitable for modifications of biomolecules to obtain a specific biological effect. We will focus on icosahedral boron clusters, as well as metallacarboranes, and their biological activity and interaction with the biological environment. Expert opinion: Boron clusters are suitable for altering structural and functional features of biomolecules and can be used in the development of new drugs and drug delivery systems. The high affinity of boron clusters, especially metallacarboranes, to albumin creates a new possibility to use them to optimize the pharmacokinetics of biologically active peptides. Boron clusters have high potential in biological and medicinal applications. Due to their peculiar properties, they can be used to optimize parameters critical for the biological activity of therapeutic substances and their affinity toward biological targets.

Design, Synthesis, and Evaluation of Novel 3-Carboranyl-1,8-Naphthalimide Derivatives as Potential Anticancer Agents

“…The biomedical application of carboranes (C 2 B 10 H 12 ) ( Figure 1 ) has been reviewed in several papers [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 ], particularly focusing on their properties that may be of importance in the design of biologically active compounds, which include the following: their ability of unique noncovalent interactions (ionic interaction, σ–hole interaction, dihydrogen bond formation); spherical or ellipsoidal geometry and rigid three-dimensional (3D) arrangement (which offer versatile platforms for 3D molecular construction); lipophilicity, amphiphilicity, or hydrophilicity (depending on the type of boron cluster used which allows modulating the pharmacokinetics and bioavailability); chemical stability as well as susceptibility to functionalization; bioorthogonality; stability in biological environments; abiotic origin; and high content of boron (important for boron neutron capture therapy, BNCT).…”

Novel Isoniazid-Carborane Hybrids Active In Vitro against Mycobacterium tuberculosis

“…The most famous is icosahedral dicarba- closo -dodecaborane (carborane, C 2 B 10 H 12 ) and its three isomeric forms: 1,2-C 2 B 10 H 12 ( ortho -), 1,7-C 2 B 10 H 12 ( meta -), and 1,12-C 2 B 10 H 12 ( para -), depending on the position of the carbon atoms within the carborane structure [ 13 ]. The biomedical application of carboranes has been discussed [ 14 , 15 , 16 , 17 , 18 ]. The properties of carborane clusters that can be used in medical chemistry include the following: inorganic nature and resistance to enzymatic degradation, susceptibility to orthogonal functionalization, the possibility of interactions with peptides, and tendency to self-assemble in an aqueous solution [ 18 ].…”

Face‐Fusion of Icosahedral Boron Hydride Increases Affinity to γ‐Cyclodextrin: closo,closo‐[B21H18]− as an Anion with Very Low Free Energy of Dehydration

“…Quantum‐chemical computations in the gas phase suggested dihydrogen bonds between the B−H vertices and the polar hydroxyl groups of CDs . Since the interaction of boron clusters with CDs in the aqueous solution phase might open novel avenues towards interactions with other water‐soluble biomolecules, we now extended our studies of B21 to the solution phase …”