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Review
. 2013 Apr;5(6):653-76.
doi: 10.4155/fmc.13.38.

Boron chemicals in diagnosis and therapeutics

Bhaskar C Das  1 , Pritam Thapa, Radha Karki, Caroline Schinke, Sasmita Das, Suman Kambhampati, Sushanta K Banerjee, Peter Van Veldhuizen, Amit Verma, Louis M Weiss, Todd Evans
Affiliations
Review

Boron chemicals in diagnosis and therapeutics

Bhaskar C Das et al. Future Med Chem. 2013 Apr.

Abstract

Advances in the field of boron chemistry have expanded the application of boron from material use to medicine. Boron-based drugs represent a new class of molecules that possess several biomedical applications including use as imaging agents for both optical and nuclear imaging as well as therapeutic agents with anticancer, antiviral, antibacterial, antifungal and other disease-specific activities. For example, bortezomib (Velcade(®)), the only drug in clinical use with boron as an active element, was approved in 2003 as a proteasome inhibitor for the treatment of multiple myeloma and non-Hodgkin's lymphoma. Several other boron-based compounds are in various phases of clinical trials, which illustrates the promise of this approach for medicinal chemists working in the area of boron chemistry. It is expected that in the near future, several boron-containing drugs should become available in the market with better efficacy and potency than existing drugs. This article discusses the current status of the development of boron-based compounds as diagnostic and therapeutic agents in humans.

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Figures

Figure 1
Figure 1
Configurational modifications of boron.
Figure 2
Figure 2. Possible mechanism of action of boron-based compounds for enzyme inhibition
(A) General mechanism of action of serine protease. (B) Boronic acid forms a transition state analog thereby causing inactivation of enzyme.
Figure 3
Figure 3
Dipyrromethene boron difluoride-labeled fluorescent probes.
Figure 4
Figure 4. Probes for in vivo labeling of cysteine cathepsins
BODIPY: Dipyrromethene boron difluoride.
Figure 5
Figure 5
Conversion of the dipyrromethene boron difluoride-2′deoxyguanosine derivative to give strong fluorescence.
Figure 6
Figure 6
Synthesis of a highly stable boronate ester.
Figure 7
Figure 7
Process of diol–boronate complex formation.
Figure 8
Figure 8
Boronate-based probes give colored and fluorescent product in the presence of H2O2.
Figure 9
Figure 9
Monoboronate probes give colored and fluorescent product in the presence of H2O2.
Figure 10
Figure 10
Aryltrifluoroborates for 18F labeling.
Figure 11
Figure 11
Binding of bis-boronic acid rhodamine dye with tetraserine motifs.
Figure 12
Figure 12
Boronic acid-containing therapeutic agents.
Figure 13
Figure 13
Bortezomib and talabostat.
Figure 14
Figure 14
Bortezomib derivatives as second-generation proteasome inhibitors.
Figure 15
Figure 15
Tripeptide boronic acid derivatives as promising proteasome inhibitors.
Figure 16
Figure 16
Boron-based chalcone as an anticancer agent.
Figure 17
Figure 17
4-hydroxytamoxifen derivatives with boron substituents.
Figure 18
Figure 18
Potent HDAC inhibitors.
Figure 19
Figure 19
Boron-based thiazolidnediones.
Figure 20
Figure 20
Boronic acid derivatives of combretastatins.
Figure 21
Figure 21
Phenoxyacetanilide derivative is a HIF-1α inhibitor.
Figure 22
Figure 22. Boron-based reactive oxygen species activated pro-drugs
(A) Nitrogen mustard prodrugs and mechanism of activation. (B) Quinone methide prodrug.
Figure 23
Figure 23
Estrogen receptor modulators.
Figure 24
Figure 24
Clinically used drugs boronophenylalanine and sodium borocaptate.
Figure 25
Figure 25. Low-molecular-weight compounds for boron neutron capture therapy
DEQ-B: Dequalinium-B.
Figure 26
Figure 26
P2–P4 macrocyclic hepatitis C virus NS3/4A protease inhibitors.
Figure 27
Figure 27
Boron-based danoprevir ITMN-191 derivatives.
Figure 28
Figure 28
NS3 protease inhibitors based on telaprevir and boceprevir templates.
Figure 29
Figure 29
Boron-based compound as HIV-1 integrase inhibitor.
Figure 30
Figure 30
Antifungal agents in clinical trials.
Figure 31
Figure 31
Thiosemicarbazones as potential antifungal agents.
Figure 32
Figure 32
Boron-based compounds as antibacterial agents.
Figure 33
Figure 33
Clinical candidates for Type 2 diabetes (89), anticoagulation (90) and human African trypanosomiasis (91).
Figure 34
Figure 34
Organotrifluoroborate salts.
Figure 35
Figure 35
Boron nitride nanotubes as a drug-delivery and targeting system.
See this image and copyright information in PMC

References

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Websites

    1. Anacor Pharmaceutical company. website. www.anacor.com.
    1. BARDA bets on boron to bust bacteria. http://cenblog.org/the-haystack/2011/09/barda-boron-bacteria.

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