Potential applications of the boron cluster compounds

Plešek, Jaromı́r

doi:10.1021/cr00010a005

Cited by 602 publications

(372 citation statements)

References 17 publications

(19 reference statements)

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“…[3] Their discovery in the 1960s led to numerous applications in medicinal chemistry and materials science, [4] among which their use in neutron capture therapy of cancer stands out as apractically relevant one. [5] Thehostguest chemistry of these hydrophilic cluster anions has not been previously described.…”

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confidence: 99%

Water Structure Recovery in Chaotropic Anion Recognition: High‐Affinity Binding of Dodecaborate Clusters to γ‐Cyclodextrin

et al. 2015

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Dodecaborate anions of the type B12X122− and B12X11Y2− (X=H, Cl, Br, I and Y=OH, SH, NH3+, NR3+) form strong (Ka up to 106 L mol−1, for B12Br122−) inclusion complexes with γ‐cyclodextrin (γ‐CD). The micromolar affinities reached are the highest known for this native CD. The complexation exhibits highly negative enthalpies (up to −25 kcal mol−1) and entropies (TΔS up to −18.4 kcal mol−1, both for B12I122−), which position these guests at the bottom end of the well‐known enthalpy‐entropy correlation for CDs. The high driving force can be traced back to a chaotropic effect, according to which chaotropic anions have an intrinsic affinity to hydrophobic cavities in aqueous solution. In line with this argument, salting‐in effects revealed dodecaborates as superchaotropic dianions.

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confidence: 99%

Water Structure Recovery in Chaotropic Anion Recognition: High‐Affinity Binding of Dodecaborate Clusters to γ‐Cyclodextrin

et al. 2015

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“…These properties are reflected in unique solution properties and ion-pairing behavior of this ion, which in turn led to its known applications in extraction chemistry (24,25) and in the development of lowest coordinating anions (26) and compounds for radioimaging (14). However, the metal bis(dicarbollides) have never been considered as biologically active compounds or pharmacophores.…”

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confidence: 99%

From nonpeptide toward noncarbon protease inhibitors: Metallacarboranes as specific and potent inhibitors of HIV protease

Cígler

Kožíšek

Řezáčová

et al. 2005

Proc. Natl. Acad. Sci. U.S.A.

285

273

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HIV protease (PR) represents a prime target for rational drug design, and protease inhibitors (PI) are powerful antiviral drugs. Most of the current PIs are pseudopeptide compounds with limited bioavailability and stability, and their use is compromised by high costs, side effects, and development of resistant strains. In our search for novel PI structures, we have identified a group of inorganic compounds, icosahedral metallacarboranes, as candidates for a novel class of nonpeptidic PIs. Here, we report the potent, specific, and selective competitive inhibition of HIV PR by substituted metallacarboranes. The most active compound, sodium hydrogen butylimino bis-8,8-[5-(3-oxa-pentoxy)-3-cobalt bis(1,2-dicarbollide)]di-ate, exhibited a Ki value of 2.2 nM and a submicromolar EC50 in antiviral tests, showed no toxicity in tissue culture, weakly inhibited human cathepsin D and pepsin, and was inactive against trypsin, papain, and amylase. The structure of the parent cobalt bis(1,2-dicarbollide) in complex with HIV PR was determined at 2.15 Å resolution by protein crystallography and represents the first carborane-protein complex structure determined. It shows the following mode of PR inhibition: two molecules of the parent compound bind to the hydrophobic pockets in the flap-proximal region of the S3 and S3 subsites of PR. We suggest, therefore, that these compounds block flap closure in addition to filling the corresponding binding pockets as conventional PIs. This type of binding and inhibition, chemical and biological stability, low toxicity, and the possibility to introduce various modifications make boron clusters attractive pharmacophores for potent and specific enzyme inhibition. rational drug design ͉ aspartic proteases ͉ carboranes ͉ x-ray structure analysis ͉ virostatics

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“…One direction of this field lies in the study of carborane cluster ligands (especially those based on o-carborane or closo-C 2 B 10 H 12 ) and their metal coordination compounds [1,2], utilizing the excellent thermal, oxidative and chemical stability and the many potential applications imparted by the carborane moieties [3,4]. Besides the well-known metallacarborane clusters [2], the ligand systems combining the o-carborane skeleton and functional groups such as cyclopentadienyls [5,6], phosphines [7 -11] and Si/Sn [12] or S/Se heteroatoms [13,14] etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure and Photoluminescence of 1,2-Bis(phenylselenyl)-1,2-dicarba-closo-dodecaborane(12)

Miao

Chen

et al. 2011

Zeitschrift Für Naturforschung B

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The reaction of dithio-o-carborane with diphenyldiselenide (PhSeSePh) affords the title compound, closo-1,2-(PhSe) 2 C 2 B 10 H 10 (1), which has been characterized by IR and NMR ( 1 H, 11 B) spectroscopy and by single-crystal X-ray diffraction. The phenylselenyl groups are bonded to the cage carbon atoms of the o-carborane cluster with a C cage -C cage distance of 1.751(6)Å and an Se-C cage -C cage -Se torsion angle of 10.1(3) • . Compound 1 displays a violet emission on excitation with UV light. For comparison the photoluminescence of the known analog closo-1,2-(PhS) 2 C 2 B 10 H 10 (2) was also studied.

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Potential applications of the boron cluster compounds

Cited by 602 publications

References 17 publications

Water Structure Recovery in Chaotropic Anion Recognition: High‐Affinity Binding of Dodecaborate Clusters to γ‐Cyclodextrin

Water Structure Recovery in Chaotropic Anion Recognition: High‐Affinity Binding of Dodecaborate Clusters to γ‐Cyclodextrin

From nonpeptide toward noncarbon protease inhibitors: Metallacarboranes as specific and potent inhibitors of HIV protease

Synthesis, Crystal Structure and Photoluminescence of 1,2-Bis(phenylselenyl)-1,2-dicarba-closo-dodecaborane(12)

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