A Kinetic Study of the Self-degradation of o-Carboranylalanine to nido-Carboranylalanine in Solution.

Svantesson, Eva; Pettersson, Jean; Olin, Åke; Markides, Karin E.; Sjöberg, Stefan

doi:10.3891/acta.chem.scand.53-0731

Cited by 23 publications

(13 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This study revealed that conjugate 15 , which contains meta ‐carborane 5 , is completely stable in aqueous solution after incubation for 24 hours at 37°C. Under the same conditions, a degradation product of conjugate 14 is slowly formed, and we suggest this to be most likely due to deboronation of the incorporated ortho ‐carborane 4 . Lützenburg et al also described that a meta ‐carborane‐modified peptide is completely stable after storage in aqueous solution for several weeks at −20°C .…”

Section: Discussionsupporting

confidence: 53%

“…Under the same conditions, a degradation product of conjugate 14 is slowly formed, and we suggest this to be most likely due to deboronation of the incorporated ortho-carborane 4. 51 Lützenburg et al also described that a meta-carborane-modified peptide is completely stable after storage in aqueous solution for several weeks at −20°C. 50 Overall, this experiment demonstrates that the stable meta-carborane with a mercaptoacetic acid linker at a boron atom is the preferred boron compound for application in BNCT.…”

Section: Modification Of Ghrr Agonists Ghrp-6 and Ipamorelin With Mmentioning

confidence: 99%

See 1 more Smart Citation

A stable meta‐carborane enables the generation of boron‐rich peptide agonists targeting the ghrelin receptor

Worm

Els‐Heindl

Kellert

et al. 2018

Journal of Peptide Science

View full text Add to dashboard Cite

Boron neutron capture therapy (BNCT) is a binary cancer therapy, which combines the biochemical targeting of a boron-containing drug with the regional localization of radiation treatment. Although the concept of BNCT has been known for decades, the selective delivery of boron into tumor cells remains challenging. G protein-coupled receptors that are overexpressed on cancer cells in combination with peptidic ligands can be potentially used as shuttle system for a tumor-directed boron uptake. In this study, we present the generation of short, boron-rich peptide conjugates that target the ghrelin receptor. Expression of the ghrelin receptor on various cancer cells makes it a viable target for BNCT. We designed a novel hexapeptide super-agonist that was modified with different specifically synthesized carborane monoclusters and tested for ghrelin receptor activation. A meta-carborane building block with a mercaptoacetic acid linker was found to be optimal for peptide modification, owing to its chemical stability and a suitable activation efficacy of the conjugate. The versatility of this carborane for the development of peptidic boron delivery agents was further demonstrated by the generation of highly potent, boron-loaded conjugates using the backbone of the known ghrelin receptor ligands growth hormone releasing peptide 6 and Ipamorelin.

show abstract

Section: Discussionsupporting

confidence: 53%

Section: Modification Of Ghrr Agonists Ghrp-6 and Ipamorelin With Mmentioning

confidence: 99%

A stable meta‐carborane enables the generation of boron‐rich peptide agonists targeting the ghrelin receptor

Worm

Els‐Heindl

Kellert

et al. 2018

Journal of Peptide Science

View full text Add to dashboard Cite

show abstract

“…It was found that the closo -carborane derivatives can be cleaved to nido -structure in solution. The spontaneous degradation was observed for racemic ortho -carboranylalanine and ortho -carboranyl-lactose conjugates in a water–methanol solution [ 25 ] and in water or methanol [ 26 ], respectively. 1,2-Bis(aminomethyl)-1,2-dicarba- closo -dodecaborane hydrochloride was also converted to an opened form in deuterated DMSO [ 27 ].…”

Section: Resultsmentioning

confidence: 99%

Novel Isoniazid-Carborane Hybrids Active In Vitro against Mycobacterium tuberculosis

et al. 2020

View full text Add to dashboard Cite

Tuberculosis (TB) is a severe infectious disease with high mortality and morbidity. The emergence of drug-resistant TB has increased the challenge to eliminate this disease. Isoniazid (INH) remains the key and effective component in the therapeutic regimen recommended by World Health Organization (WHO). A series of isoniazid-carborane derivatives containing 1,2-dicarba-closo-dodecaborane, 1,7-dicarba-closo-dodecaborane, 1,12-dicarba-closo-dodecaborane, or 7,8-dicarba-nido-undecaborate anion were synthesized for the first time. The compounds were tested in vitro against the Mycobacterium tuberculosis (Mtb) H37Rv strain and its mutant (ΔkatG) defective in the synthesis of catalase-peroxidase (KatG). N′-((7,8-dicarba-nido-undecaboranyl)methylidene)isonicotinohydrazide (16) showed the highest activity against the wild-type Mtb strain. All hybrids could inhibit the growth of the ΔkatG mutant in lower concentrations than INH. N′-([(1,12-dicarba-closo-dodecaboran-1yl)ethyl)isonicotinohydrazide (25) exhibited more than 60-fold increase in activity against Mtb ΔkatG as compared to INH. This compound was also found to be noncytotoxic up to a concentration four times higher than the minimum inhibitory concentration 99% (MIC99) value.

show abstract

“…It should be noted that it comes as a surprise that treatment of 3-aminocarborane derivative in strongly acidic medium results in its deboronation, since to our knowledge, the deboronation of closo-dodecaboranes has been described in the literature under neutral conditions [8] or basic conditions, in the presence of the powerful Lewis bases [9]. Thus, instead of the individual enantiomers of carborane 2 we obtained 7,8-dicarbanido-undecaborane derivative 7 as a result of acidic hydrolysis of amides 5 and 6.…”

Section: Resultsmentioning

confidence: 94%

Acidic hydrolysis of N-acyl-1-substituted 3-amino-1,2-dicarba-closo-dodecaboranes

Левит

Demin

Кодесс

et al. 2005

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

A Kinetic Study of the Self-degradation of o-Carboranylalanine to nido-Carboranylalanine in Solution.

Cited by 23 publications

References 0 publications

A stable meta‐carborane enables the generation of boron‐rich peptide agonists targeting the ghrelin receptor

A stable meta‐carborane enables the generation of boron‐rich peptide agonists targeting the ghrelin receptor

Novel Isoniazid-Carborane Hybrids Active In Vitro against Mycobacterium tuberculosis

Acidic hydrolysis of N-acyl-1-substituted 3-amino-1,2-dicarba-closo-dodecaboranes

Contact Info

Product

Resources

About