Home / Articles / Cyclic oxonium derivatives of cobalt and iron bis(dicarbollides) and their use in organic synthesis

Cyclic oxonium derivatives of cobalt and iron bis(dicarbollides) and their use in organic synthesis

Anna Aleksandrovna Druzina 1
Anna Aleksandrovna Druzina
, 
Akim Vladimirovich Shmalko 1
Akim Vladimirovich Shmalko
, 
Igor Borisovich Sivaev 1
Igor Borisovich Sivaev
, 
Vladimir Iosifovich Bregadze 1
Vladimir Iosifovich Bregadze
1 A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Moscow
10.1070/RCR5000
Published 30 November 2020
Review , RCR5000, Volume 90, Issue 7, 785-830
38
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Druzina A. A. et al. Cyclic oxonium derivatives of cobalt and iron bis(dicarbollides) and their use in organic synthesis // Russian Chemical Reviews. 2020. Vol. 90. No. 7. pp. 785-830.
GOST all authors (up to 50)
Copy cite
Druzina A. A., Shmalko A. V., Sivaev I. B., Bregadze V. I. Cyclic oxonium derivatives of cobalt and iron bis(dicarbollides) and their use in organic synthesis // Russian Chemical Reviews. 2020. Vol. 90. No. 7. pp. 785-830.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RCR5000
UR - https://rcr.colab.ws/publications/10.1070/RCR5000
TI - Cyclic oxonium derivatives of cobalt and iron bis(dicarbollides) and their use in organic synthesis
T2 - Russian Chemical Reviews
AU - Druzina, Anna Aleksandrovna
AU - Shmalko, Akim Vladimirovich
AU - Sivaev, Igor Borisovich
AU - Bregadze, Vladimir Iosifovich
PY - 2020
DA - 2020/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 785-830
IS - 7
VL - 90
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{2020_Druzina,
author = {Anna Aleksandrovna Druzina and Akim Vladimirovich Shmalko and Igor Borisovich Sivaev and Vladimir Iosifovich Bregadze},
title = {Cyclic oxonium derivatives of cobalt and iron bis(dicarbollides) and their use in organic synthesis},
journal = {Russian Chemical Reviews},
year = {2020},
volume = {90},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR5000},
number = {7},
pages = {785--830},
doi = {10.1070/RCR5000}
}
MLA
Cite this
MLA
Copy cite
Druzina, Anna Aleksandrovna, et al. “Cyclic oxonium derivatives of cobalt and iron bis(dicarbollides) and their use in organic synthesis.” Russian Chemical Reviews, vol. 90, no. 7, Nov. 2020, pp. 785-830. https://rcr.colab.ws/publications/10.1070/RCR5000.
Views / Visits / Downloads
27 / 27 / 7

Keywords

boron neutron capture therapy of cancer
cobalt and iron bis(dicarbollide)s
cyclic oxonium derivatives
nucleophilic ring-opening

Abstract

The rapid progress in the chemistry of carboranes and other polyhedral boron compounds makes the development of methods for the synthesis of their various functional derivatives a high priority. The formation of cyclic oxonium derivatives followed by the ring opening is one of the most efficient methods for the preparation of these compounds. This review addresses the data on the use of the nucleophilic ring opening of cyclic oxonium derivatives based on cobalt and iron bis(dicarbollides), which have been extensively studied in recent years. Reactions involving O-, N-, S-, P- and C-nucleophiles are considered as a route to the targeted synthesis of a wide range of organic boron derivatives, in particular various boron-containing biologically active compounds. Possible applications of the reaction products are discussed.

The bibliography includes 197 references.

Funders

Russian Foundation for Basic Research
19-13-50459 Экспансия
Ministry of Education and Science of the Russian Federation

References

1.
2  Highlights in inorganic chemistry over the last 100 years
McCleverty J.A.
Annual Reports Section A (Inorganic Chemistry) , 2004
4.
Hückel's Rule of Aromaticity Categorizes Aromatic closo Boron Hydride Clusters.
Poater J., Solà M., Viñas C., Teixidor F.
Chemistry - A European Journal , 2016
5.
Too Persistent to Give Up: Aromaticity in Boron Clusters Survives Radical Structural Changes
Poater J., Viñas C., Bennour I., Escayola S., Solà M., Teixidor F.
Journal of the American Chemical Society , 2020
6.
A Carbon-Free Sandwich Complex [(P 5 ) 2 Ti] 2−
Urne˙žius E., Brennessel W.W., Cramer C.J., Ellis J.E., Schleyer P.V.
Science , 2002
9.
Beyond organic chemistry: aromaticity in atomic clusters
Boldyrev A.I., Wang L.
Physical Chemistry Chemical Physics , 2016
10.
rcr_90_7_785bib10
Chattaraj
2011
11.
rcr_90_7_785bib11
Grimes
2016
13.
Sivaev I.B., Bregadze V.I., Sjöberg S.
Collection of Czechoslovak Chemical Communications , 2002
14.
Sivaev I.B., Bregadze V.I.
Collection of Czechoslovak Chemical Communications , 1999
15.
Cobalt bis(dicarbollide) anion and its derivatives
Dash B.P., Satapathy R., Swain B.R., Mahanta C.S., Jena B.B., Hosmane N.S.
Journal of Organometallic Chemistry , 2017
16.
rcr_90_7_785bib16
Sivaev
2009
17.
rcr_90_7_785bib17
Romanovsky
2011
18.
rcr_90_7_785bib18
Rais
2004
19.
rcr_90_7_785bib19
Grüner
2012
20.
rcr_90_7_785bib20
Bregadze
2012
21.
Synthesis of crown ethers with the incorporated cobalt bis(dicarbollide) fragment
Kazakov G.S., Stogniy M.Y., Sivaev I.B., Suponitsky K.Y., Godovikov I.A., Kirilin A.D., Bregadze V.I.
Journal of Organometallic Chemistry , 2015
22.
Metallacarborane-Based Metal–Organic Framework with a Complex Topology
Kennedy R.D., Clingerman D.J., Morris W., Wilmer C.E., Sarjeant A.A., Stern C.L., O’Keeffe M., Snurr R.Q., Hupp J.T., Farha O.K., Mirkin C.A.
Crystal Growth and Design , 2014
23.
Tetrathiafulvalene-based radical cation salts with transition metal bis(dicarbollide) anions
Bregadze V.I., Dyachenko O.A., Kazheva O.N., Kravchenko A.V., Sivaev I.B., Starodub V.A.
CrystEngComm , 2015
24.
Electroconducting Radical-Cation Salts Based on Tetrathiafulvalene Derivatives and Transition Metals Bis(dicarbollides)
Bregadze V.I., Dyachenko O.A., Kazheva O.N., Kosenko I.D., Kravchenko A.V., Sivaev I.B., Starodub V.A.
Russian Journal of General Chemistry , 2019
25.
How to get the desired reduction voltage in a single framework! Metallacarborane as an optimal probe for sequential voltage tuning
Tarrés M., Arderiu V.S., Zaulet A., Viñas C., Fabrizi de Biani F., Teixidor F.
Dalton Transactions , 2015
26.
Electron Accumulative Molecules
Buades A.B., Sanchez Arderiu V., Olid-Britos D., Viñas C., Sillanpää R., Haukka M., Fontrodona X., Paradinas M., Ocal C., Teixidor F.
Journal of the American Chemical Society , 2018
27.
rcr_90_7_785bib27
Pichaandi
2018
28.
rcr_90_7_785bib28
Sivaev
Int. Ed. , 2018
29.
Structural and dielectric properties of cobaltacarborane composite polybenzimidazole membranes as solid polymer electrolytes at high temperature
Fuentes I., Andrio A., García-Bernabé A., Escorihuela J., Viñas C., Teixidor F., Compañ V.
Physical Chemistry Chemical Physics , 2018
30.
Expanding the chemistry of single‐ion conducting poly(ionic liquid)s with polyhedral boron anions
Lozinskaya E.I., Cotessat M., Shmalko A.V., Ponkratov D.O., Gumileva L.V., Sivaev I.B., Shaplov A.S.
Polymer International , 2019
31.
rcr_90_7_785bib31
Řezačova
2012
32.
Metallacarborane Sulfamides: Unconventional, Specific, and Highly Selective Inhibitors of Carbonic Anhydrase IX
Grüner B., Brynda J., Das V., Šícha V., Štěpánková J., Nekvinda J., Holub J., Pospíšilová K., Fábry M., Pachl P., Král V., Kugler M., Mašek V., Medvedíková M., Matějková S., et. al.
Journal of Medicinal Chemistry , 2019
33.
A Highly Potent Antibacterial Agent Targeting Methicillin-Resistant Staphylococcus aureus Based on Cobalt Bis(1,2-Dicarbollide) Alkoxy Derivative
Zheng Y., Liu W., Chen Y., Jiang H., Yan H., Kosenko I., Chekulaeva L., Sivaev I., Bregadze V., Wang X.
Organometallics , 2017
34.
rcr_90_7_785bib34
Vakova
J. Organomet. Chem. , 2019
35.
DNA Modified with Boron–Metal Cluster Complexes [M(C2B9H11)2]—Synthesis, Properties, and Applications
Olejniczak A., Nawrot B., Leśnikowski Z.
International Journal of Molecular Sciences , 2018
36.
Metallacarboranes on the Road to Anticancer Therapies: Cellular Uptake, DNA Interaction, and Biological Evaluation of Cobaltabisdicarbollide [COSAN]−
Fuentes I., García-Mendiola T., Sato S., Pita M., Nakamura H., Lorenzo E., Teixidor F., Marques F., Viñas C.
Chemistry - A European Journal , 2018
37.
Fast flip–flop of halogenated cobalt bis(dicarbollide) anion in a lipid bilayer membrane
Rokitskaya T.I., Kosenko I.D., Sivaev I.B., Antonenko Y.N., Bregadze V.I.
Physical Chemistry Chemical Physics , 2017
38.
High-Affinity Binding of Metallacarborane Cobalt Bis(dicarbollide) Anions to Cyclodextrins and Application to Membrane Translocation
Assaf K.I., Begaj B., Frank A., Nilam M., Mougharbel A.S., Kortz U., Nekvinda J., Grüner B., Gabel D., Nau W.M.
Journal of Organic Chemistry , 2019
39.
rcr_90_7_785bib39
Sauerwein
2012
40.
Determination of boron by inductively coupled plasma atomic emission spectroscopy. Biodistribution of 10B in tumor-bearing mice
Tsygankova A.R., Kanygin V.V., Kasatova A.I., Zav’yalov E.L., Gusel’nikova T.Y., Kichigin A.I., Mukhamadiyarov R.A.
Russian Chemical Bulletin , 2020
42.
The Chemistry of Neutron Capture Therapy
Soloway A.H., Tjarks W., Barnum B.A., Rong F., Barth R.F., Codogni I.M., Wilson J.G.
Chemical Reviews , 1998
43.
rcr_90_7_785bib43
Sivaev
Ros. Khim. Zh. , 2004
44.
rcr_90_7_785bib44
Sivaev
2009
45.
Boron agents for neutron capture therapy
Hu K., Yang Z., Zhang L., Xie L., Wang L., Xu H., Josephson L., Liang S.H., Zhang M.
Coordination Chemistry Reviews , 2020
46.
rcr_90_7_785bib46
Semioshkin
2008
47.
rcr_90_7_785bib47
Sivaev
2012
49.
rcr_90_7_785bib49
Llop
2003
50.
Chameleonic Capacity of [3,3‘-Co(1,2-C2B9H11)2]- in Coordination. Generation of the Highly Uncommon S(thioether)−Na Bond
Teixidor F., Pedrajas J., Rojo I., Viñas C., Kivekäs R., Sillanpää R., Sivaev I., Bregadze V., Sjöberg S.
Organometallics , 2003
51.
Chemistry of nickel and iron bis(dicarbollides). A review
Sivaev I.B., Bregadze V.I.
Journal of Organometallic Chemistry , 2000
53.
Synthesis and the structure of 8-tetrahydrofuronium and 8-tetrahydropyronium derivatives of iron bis(dicarbollide)(-I) and their cleavage reactions
Lobanova I., Kosenko I., Laskova J., Ananyev I., Druzina A., Godovikov I., Bregadze V.I., Qi S., Leśnikowski Z.J., Semioshkin A.
Dalton Transactions , 2015
54.
rcr_90_7_785bib54
Tarrés
Chem. – Eur. J. , 2014
55.
Synthesis of functional derivatives of the [3,3′-Co(1,2-C2B9H11)2]− anion
Sivaev I.B., Starikova Z.A., Sjöberg S., Bregadze V.I.
Journal of Organometallic Chemistry , 2002
56.
Low-Melting Salts Based on a Glycolated Cobalt Bis(dicarbollide) Anion
Rak J., Jakubek M., Kaplánek R., Král V.
Inorganic Chemistry , 2012
57.
rcr_90_7_785bib57
Cígler
Proc. Natl. Acad. Sci. USA , 2005
59.
CMP(O) tripodands: synthesis, potentiometric studies and extractions
Reinoso-García M.M., Jańczewski D., Reinhoudt D.N., Verboom W., Malinowska E., Pietrzak M., Hill C., Báča J., Grüner B., Selucky P., Grüttner C.
New Journal of Chemistry , 2006
61.
On the Solubility and Lipophilicity of Metallacarborane Pharmacophores
Rak J., Dejlová B., Lampová H., Kaplánek R., Matějíček P., Cígler P., Král V.
Molecular Pharmaceutics , 2013
62.
Aqueous Self-Assembly and Cation Selectivity of Cobaltabisdicarbollide Dianionic Dumbbells
Tarrés M., Viñas C., González-Cardoso P., Hänninen M.M., Sillanpää R., Ďorďovič V., Uchman M., Teixidor F., Matějíček P.
Chemistry - A European Journal , 2014
63.
Synthesis of carboxylic acids based on the closo-decaborate anion
Prikaznov A.V., Shmal’ko A.V., Sivaev I.B., Petrovskii P.V., Bragin V.I., Kisin A.V., Bregadze V.V.
Polyhedron , 2011
65.
Crown ether substituted cobalta bis(dicarbollide) ions as selective extraction agents for removal of Cs+ and Sr2+ from nuclear waste
Grüner B., Plešek J., Báča J., Francois Dozol J., Lamare V., Císařová I., Bělohradský M., Čáslavský J.
New Journal of Chemistry , 2002
66.
rcr_90_7_785bib66
Teixidor
Chem. – Eur. J. , 2015
67.
rcr_90_7_785bib67
Teixidor
Chem. – Eur. J. , 2015
68.
“Chemical Ligation”: A Versatile Method for Nucleoside Modification with Boron Clusters
Wojtczak B., Andrysiak A., Grüner B., Lesnikowski Z.
Chemistry - A European Journal , 2008
69.
Druzina Anna Alexandrovna, Shmalko Akim Vladimirovich, Andreichuk Ekaterina Petrovna, Zhidkova Olga Borisovna, Kosenko Irina Dmitrievna, Semioshkin Andrey Anatol'evich, Sivaev Igor Borisovich, Mandal Swadhin, Shen Zheyu, Bregadze Vladimir Iosifovich
Mendeleev Communications , 2019
70.
rcr_90_7_785bib70
Kosenko
Int. Ed. , 2013
71.
Metallacarboranes as Building Blocks for Polyanionic Polyarmed Aryl-Ether Materials
Farràs P., Teixidor F., Kivekäs R., Sillanpää R., Viñas C., Grüner B., Cisarova I.
Inorganic Chemistry , 2008
72.
Decorating Poly(alkyl aryl-ether) Dendrimers with Metallacarboranes
Núñez R., Juárez-Pérez E.J., Teixidor F., Santillan R., Farfán N., Abreu A., Yépez R., Viñas C.
Inorganic Chemistry , 2010
74.
rcr_90_7_785bib74
Hao
2005
75.
New boron-containing bacteriochlorin p cycloimide conjugate
Grin M.A., Titeev R.A., Bakieva O.M., Brittal D.I., Lobanova I.A., Sivaev I.B., Bregadze V.I., Mironov A.F.
Russian Chemical Bulletin , 2008
76.
Redox-Active Metallacarborane-Decorated Octasilsesquioxanes. Electrochemical and Thermal Properties
Cabrera-González J., Sánchez-Arderiu V., Viñas C., Parella T., Teixidor F., Núñez R.
Inorganic Chemistry , 2016
77.
rcr_90_7_785bib77
Shmal’ko
Inorg. Lett. , 2015
78.
rcr_90_7_785bib78
Shmal’ko
2016
79.
Facile Synthetic Routes to Phenylene and Triazine Core Based Dendritic Cobaltabisdicarbollides
Dash B.P., Satapathy R., Maguire J.A., Hosmane N.S.
Organometallics , 2010
81.
Cobaltabisdicarbollide based metallodendrimers with cyclotriphosphazene core
Mahanta C.S., Bhavsar R., Dash B.P., Satapathy R.
Journal of Organometallic Chemistry , 2018
82.
rcr_90_7_785bib82
Mikulašek
2006
83.
rcr_90_7_785bib83
Mikulašek
2007
84.
rcr_90_7_785bib84
Grüner
2005
85.
Metallacarborane Assemblies as Effective Antimicrobial Agents, Including a Highly Potent Anti-MRSA Agent
Romero I., Martinez-Medina M., Camprubí-Font C., Bennour I., Moreno D., Martínez-Martínez L., Teixidor F., Fox M.A., Viñas C.
Organometallics , 2020
86.
Preparation, characterization, and the selective antimicrobial activity of N-alkylammonium 8-diethyleneglycol cobalt bis-dicarbollide derivatives
Kvasničková E., Masák J., Čejka J., Maťátková O., Šícha V.
Journal of Organometallic Chemistry , 2017
88.
Synthesis of naphthalimide-carborane and metallacarborane conjugates: Anticancer activity, DNA binding ability
Nekvinda J., Różycka D., Rykowski S., Wyszko E., Fedoruk-Wyszomirska A., Gurda D., Orlicka-Płocka M., Giel-Pietraszuk M., Kiliszek A., Rypniewski W., Bachorz R., Wojcieszak J., Grüner B., Olejniczak A.B.
Bioorganic Chemistry , 2020
89.
Reversibly Switchable Fluorescent Molecular Systems Based on Metallacarborane–Perylenediimide Conjugates
Parejo L., Chaari M., Santiago S., Guirado G., Teixidor F., Núñez R., Hernando J.
Chemistry - A European Journal , 2020
90.
Nitric Oxide Synthases Activation and Inhibition by Metallacarborane-Cluster-Based Isoform-Specific Affectors
Kaplánek R., Martásek P., Grüner B., Panda S., Rak J., Masters B.S., Král V., Roman L.J.
Journal of Medicinal Chemistry , 2012
91.
Cobalt bis(dicarbollide) ions with covalently bonded CMPO groups as selective extraction agents for lanthanide and actinide cations from highly acidic nuclear waste solutions
Grüner B., Plešek J., Báča J., Císařová I., Dozol J.F., Rouquette H., Viňas C., Selucký P., Rais J.
New Journal of Chemistry , 2002
92.
Lanthanide and actinide extractions with anionic ligands based on cobalt bis(dicarbollide) ions with covalently bonded CMPO functions
Selucký P., Rais J., Lučaníková M., Grüner B., Kvíčalová M., Fejfarová K., Císařová I.
Radiochimica Acta , 2008
93.
Grin Mikhail Alexandrovich, Titeev Rustam Anvarovich, Brittal Dmitry Igorevich, Ulybina Olga V, Tsiprovskiy Alexander Gennad'evich, Berzina Maria Yanovna, Lobanova Irina Anatol'evna, Sivaev Igor Borisovich, Bregadze Vladimir Iosifovich, Mironov Andrey Fedorovich
Mendeleev Communications , 2011
94.
Design of HIV Protease Inhibitors Based on Inorganic Polyhedral Metallacarboranes
Řezáčová P., Pokorná J., Brynda J., Kožíšek M., Cígler P., Lepšík M., Fanfrlík J., Řezáč J., Grantz Šašková K., Sieglová I., Plešek J., Šícha V., Grüner B., Oberwinkler H., Sedláček’ J., et. al.
Journal of Medicinal Chemistry , 2009
95.
Capturing a dynamically interacting inhibitor by paramagnetic NMR spectroscopy
Srb P., Svoboda M., Benda L., Lepšík M., Tarábek J., Šícha V., Grüner B., Grantz-Šašková K., Brynda J., Řezáčová P., Konvalinka J., Veverka V.
Physical Chemistry Chemical Physics , 2019
96.
rcr_90_7_785bib96
Druzina
2020
97.
Selective Host-Guest Binding of Anions without Auxiliary Hydrogen Bonds: Entropy as an Aid to Design
Ursu A., Schmidtchen F.P.
Angewandte Chemie - International Edition , 2011
98.
Controlling the Pirouetting Motion in Rotaxanes by Counterion Exchange
Farràs P., Escudero-Adán E.C., Viñas C., Teixidor F.
Inorganic Chemistry , 2014
99.
Lanthanide and actinide extractions with cobalt bis(dicarbollide) ion derivatives covalently bonded to diglycolyl diamide platform
Lučaníková M., Selucký P., Rais J., Grüner B., Kvíčalová M.
Proceedings in Radiochemistry , 2011
100.
Highly Dispersible and Stable Anionic Boron Cluster-Graphene Oxide Nanohybrids
Cabrera-González J., Cabana L., Ballesteros B., Tobias G., Núñez R.
Chemistry - A European Journal , 2016
101.
Grafting of Metallacarboranes onto Self-Assembled Monolayers Deposited on Silicon Wafers
Juárez-Pérez E.J., Granier M., Viñas C., Mutin P.H., Núñez R.
Chemistry - An Asian Journal , 2011
102.
rcr_90_7_785bib102
Kosenko
Vestn. Lobachevsk. Univ. Nizhni Novgorod , 2013
104.
Cyanide free contraction of disclosed 1,4-dioxane ring as a route to cobalt bis(dicarbollide) derivatives with short spacer between the boron cage and terminal functional group
Shmal'ko A.V., Stogniy M.Y., Kazakov G.S., Anufriev S.A., Sivaev I.B., Kovalenko L.V., Bregadze V.I.
Dalton Transactions , 2015
105.
On relative electronic effects of polyhedral boron hydrides
Sivaev I.B., Prikaznov A.V., Anufriev S.A.
Journal of Organometallic Chemistry , 2013
106.
Syntheses of C-substituted icosahedral dicarbaboranes bearing the 8-dioxane-cobalt bisdicarbollide moiety
Šícha V., Farràs P., Štíbr B., Teixidor F., Grüner B., Viñas C.
Journal of Organometallic Chemistry , 2009
107.
Targeting amino acid metabolism for cancer therapy
Lukey M.J., Katt W.P., Cerione R.A.
Drug Discovery Today , 2017
108.
Human L-type amino acid transporter 1 (LAT1): characterization of function and expression in tumor cell lines
Yanagida O., Kanai Y., Chairoungdua A., Kim D.K., Segawa H., Nii T., Cha S.H., Matsuo H., Fukushima J., Fukasawa Y., Tani Y., Taketani Y., Uchino H., Kim J.Y., Inatomi J., et. al.
Biochimica et Biophysica Acta - Biomembranes , 2001
109.
Zhao Y., Wang L., Pan J.
Intractable and Rare Diseases Research , 2015
110.
The L-Type Amino Acid Transporter LAT1—An Emerging Target in Cancer
Häfliger P., Charles R.
International Journal of Molecular Sciences , 2019
111.
The synthesis and use of boronated amino acids for boron neutron capture therapy.
Kabalka G.W., Yao M.
Anti-Cancer Agents in Medicinal Chemistry , 2006
113.
Biological evaluation of boronated unnatural amino acids as new boron carriers
Kabalka G.W., Yao M.-., Marepally S.R., Chandra S.
Applied Radiation and Isotopes , 2009
114.
Boron delivery for boron neutron capture therapy targeting a cancer-upregulated oligopeptide transporter
Miyabe J., Ohgaki R., Saito K., Wei L., Quan L., Jin C., Liu X., Okuda S., Nagamori S., Ohki H., Yoshino K., Inohara H., Kanai Y.
Journal of Pharmacological Sciences , 2019
115.
Synthesis of boron-containing tyrosine derivatives based on the closo-decaborate and closo-dodecaborate anions
Prikaznov A.V., Las’kova Y.N., Semioshkin A.A., Sivaev I.B., Kisin A.V., Bregadze V.I.
Russian Chemical Bulletin , 2011
116.
Synthesis of new carborane-based amino acids
Stogniy M.Y., Zakharova M.V., Sivaev I.B., Godovikov I.A., Chizov A.O., Bregadze V.I.
Polyhedron , 2013
117.
Biological evaluation of dodecaborate-containing L-amino acids for boron neutron capture therapy.
Hattori Y., Kusaka S., Mukumoto M., Uehara K., Asano T., Suzuki M., Masunaga S., Ono K., Tanimori S., Kirihata M.
Journal of Medicinal Chemistry , 2012
118.
Evaluation of a novel sodium borocaptate-containing unnatural amino acid as a boron delivery agent for neutron capture therapy of the F98 rat glioma
Futamura G., Kawabata S., Nonoguchi N., Hiramatsu R., Toho T., Tanaka H., Masunaga S., Hattori Y., Kirihata M., Ono K., Kuroiwa T., Miyatake S.
Radiation Oncology , 2017
120.
Synthesis of new acids based on bis(dicarbollide)cobalt
Shmal’ko A.V., Sivaev I.B., Bregadze V.I., Kovalenko L.V.
Russian Chemical Bulletin , 2014
121.
A novel approach to the synthesis of amino acids based on cobalt bis(dicarbollide)
Lobanova I.A., Berzina M.Y., Sivaev I.B., Petrovskii P.V., Bregadze V.I.
Russian Chemical Bulletin , 2010
122.
rcr_90_7_785bib122
Patel
J. Chem. Pharm. Res. , 2012
124.
Advances in the basic and clinical applications of thymosin β4
Goldstein A.L., Kleinman H.K.
Expert Opinion on Biological Therapy , 2015
125.
Myocardial regeneration: expanding the repertoire of thymosin β4 in the ischemic heart
Smart N., Bollini S., Dubé K.N., Vieira J.M., Zhou B., Riegler J., Price A.N., Lythgoe M.F., Davidson S., Yellon D., Pu W.T., Riley P.R.
Annals of the New York Academy of Sciences , 2012
126.
Thymosin β4 and Ac-SDKP: Tools to mend a broken heart
Rossdeutsch A., Smart N., Riley P.R.
Journal of Molecular Medicine , 2007
127.
Synthesis and Biological Activity of Thymosin β4-Anionic Boron Cluster Conjugates
Fink K., Kobak K., Kasztura M., Boratyński J., Goszczyński T.M.
Bioconjugate Chemistry , 2018
128.
Metallacarboranes as a tool for enhancing the activity of therapeutic peptides
Fink K., Boratyński J., Paprocka M., Goszczyński T.M.
Annals of the New York Academy of Sciences , 2019
129.
rcr_90_7_785bib129
Hamblin
2008
130.
The role of porphyrin chemistry in tumor imaging and photodynamic therapy
Ethirajan M., Chen Y., Joshi P., Pandey R.K.
Chemical Society Reviews , 2011
131.
rcr_90_7_785bib131
Liu
2017
132.
Polyhedral boron derivatives of porphyrins and phthalocyanines
BREGADZE V.I., SIVAEV I.B., GABEL D., WÖHRLE D.
Journal of Porphyrins and Phthalocyanines , 2002
133.
Recent Progress in the Syntheses and Biological Evaluation of Boronated Porphyrins for Boron Neutron-Capture Therapy
Renner M.W., Miura M., Easson M.W., Vicente M.G.
Anti-Cancer Agents in Medicinal Chemistry , 2006
135.
Boron-Containing Conjugates of Natural Chlorophylls
Grin M.A., Brittal D.I., Tsiprovskiy A.G., Bregadze V.I., Mironov A.F.
Macroheterocycles , 2010
136.
Boron-Containing Phthalocyanines and Porphyrazines
Sivaev I.B., Bregadze V.I., Gül A., Mironov A.F.
Macroheterocycles , 2012
137.
Carboranyl-porphyrazines and derivatives for boron neutron capture therapy: From synthesis to in vitro tests
Pietrangeli D., Rosa A., Ristori S., Salvati A., Altieri S., Ricciardi G.
Coordination Chemistry Reviews , 2013
138.
ÖZÇELİK Ş., GÜL A.
Turkish Journal of Chemistry , 2014
139.
rcr_90_7_785bib139
Ol’shevskaya
2018
140.
rcr_90_7_785bib140
Semioshkin
2014
142.
Cobaltacarborane–phthalocyanine conjugates: Syntheses and photophysical properties
Li H., Fronczek F.R., Vicente M.G.
Journal of Organometallic Chemistry , 2009
143.
rcr_90_7_785bib143
Nar
2018
145.
Synthesis and in vitro study of new highly boronated phthalocyanine
Shmal'ko A.V., Efremenko A.V., Ignatova A.A., Sivaev I.B., Feofanov A.V., Hamuryudan E., Gül A., Kovalenko L.V., Qi S., Bregadze V.I.
Journal of Porphyrins and Phthalocyanines , 2014
146.
Synthesis and Cellular Studies of Porphyrin−Cobaltacarborane Conjugates
Hao E., Jensen T.J., Courtney B.H., Vicente M.G.
Bioconjugate Chemistry , 2005
147.
Synthesis and Spectroelectrochemistry of N-Cobaltacarborane Porphyrin Conjugates
Hao E., Zhang M., E W., Kadish K.M., Fronczek F.R., Courtney B.H., Vicente M.G.
Bioconjugate Chemistry , 2008
148.
Tetraphenylporphyrin-cobalt(III) Bis(1,2-dicarbollide) Conjugates:  From the Solution Characteristics to Inhibition of HIV Protease
Kubát P., Lang K., Cígler P., Kožíšek M., Matějíček P., Janda P., Zelinger Z., Procházka K., Král V.
Journal of Physical Chemistry B , 2007
149.
Enhanced Cellular Uptake with a Cobaltacarborane−Porphyrin−HIV-1 Tat 48−60 Conjugate
Sibrian-Vazquez M., Hao E., Jensen T.J., Vicente M.G.
Bioconjugate Chemistry , 2006
150.
Synthesis, Aggregation and Cellular Investigations of Porphyrin–Cobaltacarborane Conjugates
Hao E., Sibrian-Vazquez M., Serem W., Garno J., Fronczek F., Vicente M. .
Chemistry - A European Journal , 2007
151.
Novel types of boronated chlorine6conjugates via ‘click chemistry’
Bregadze V.I., Semioshkin A.A., Las'kova J.N., Berzina M.Y., Lobanova I.A., Sivaev I.B., Grin M.A., Titeev R.A., Brittal D.I., Ulybina O.V., Chestnova A.V., Ignatova A.A., Feofanov A.V., Mironov A.F.
Applied Organometallic Chemistry , 2009
152.
Synthesis of cobalt bis(dicarbollide) conjugates with natural chlorins by the Sonogashira reaction
Grin M.A., Titeev R.A., Brittal D.I., Chestnova A.V., Feofanov A.V., Lobanova I.A., Sivaev I.B., Bregadze V.I., Mironov A.F.
Russian Chemical Bulletin , 2010
153.
Cobalt bis(dicarbollide) versus closo-dodecaborate in boronated chlorin e(6) conjugates: implications for photodynamic and boron-neutron capture therapy.
Efremenko A.V., Ignatova A.A., Borsheva A.A., Grin M.A., Bregadze V.I., Sivaev I.B., Mironov A.F., Feofanov A.V.
Photochemical and Photobiological Sciences , 2012
154.
Chlorin e6fused with a cobalt-bis(dicarbollide) nanoparticle provides efficient boron delivery and photoinduced cytotoxicity in cancer cells
Efremenko A.V., Ignatova A.A., Grin M.A., Sivaev I.B., Mironov A.F., Bregadze V.I., Feofanov A.V.
Photochemical and Photobiological Sciences , 2013
155.
rcr_90_7_785bib155
Volovetsky
Modern Technol. Med. , 2016
156.
Pharmacokinetics of Chlorin e6-Cobalt Bis(Dicarbollide) Conjugate in Balb/c Mice with Engrafted Carcinoma
Volovetsky A., Sukhov V., Balalaeva I., Dudenkova V., Shilyagina N., Feofanov А., Efremenko A., Grin M., Mironov A., Sivaev I., Bregadze V., Maslennikova A.
International Journal of Molecular Sciences , 2017
157.
Conjugate of chlorin е6 with iron bis(dicarbollide) nanocluster: synthesis and biological properties
Ignatova A.A., Korostey Y.S., Fedotova M.K., Sivaev I.B., Bregadze V.I., Mironov A.F., Grin M.A., Feofanov A.V.
Future Medicinal Chemistry , 2020
158.
Boron and nucleic acid chemistries: merging the best of both worlds
Martin A.R., Vasseur J., Smietana M.
Chemical Society Reviews , 2013
159.
rcr_90_7_785bib159
Lesnikowski
2003
160.
Lesnikowski Z.J.
Collection of Czechoslovak Chemical Communications , 2008
162.
Synthesis of conjugates of polyhedral boron hydrides with nucleosides
Druzina A.A., Bregadze V.I., Mironov A.F., Semioshkin A.A.
Russian Chemical Reviews , 2016
163.
rcr_90_7_785bib163
Nakamura
2012
164.
3-Carboranyl Thymidine Analogues (3CTAs) and Other Boronated Nucleosides for Boron Neutron Capture Therapy
Byun Y., Narayanasamy S., Johnsamuel J., Bandyopadhyaya A.K., Tiwari R., Al-Madhoun A.S., Barth R.F., Eriksson S., Tjarks W.
Anti-Cancer Agents in Medicinal Chemistry , 2006
165.
Nucleoside and Oligonucleoside Boranophosphates:  Chemistry and Properties
Li P., Sergueeva Z.A., Dobrikov M., Shaw B.R.
Chemical Reviews , 2007
166.
N3-substituted thymidine bioconjugates for cancer therapy and imaging
Khalil A., Ishita K., Ali T., Tjarks W.
Future Medicinal Chemistry , 2013
167.
A Nucleoside Conjugate Containing a Metallacarborane Group and Its Incorporation into a DNA Oligonucleotide
Olejniczak A.B., Plešek J., Křiž O., Lesnikowski Z.J.
Angewandte Chemie - International Edition , 2003
168.
Nucleoside-metallacarborane conjugates for base-specific metal labeling of DNA.
Olejniczak A.B., Plešek J., Leśnikowski Z.J.
Chemistry - A European Journal , 2006
169.
DNA-Dinucleotides Bearing a 3‘,3‘-Cobalt- or 3‘,3‘-Iron-1,2,1‘,2‘-dicarbollide Complex
Olejniczak A.B., Mucha P., Grüner B., Lesnikowski Z.J.
Organometallics , 2007
171.
Click Chemistry: Diverse Chemical Function from a Few Good Reactions
Kolb H.C., Finn M.G., Sharpless K.B.
Angewandte Chemie - International Edition , 2001
172.
rcr_90_7_785bib172
Ebenryter-Olbin’ska
Chem. – Eur. J. , 2017
173.
Metallacarborane Complex Boosts the Rate of DNA Oligonucleotide Hydrolysis in the Reaction Catalyzed by Snake Venom Phosphodiesterase
Kaniowski D., Kulik K., Ebenryter-Olbińska K., Wielgus E., Lesnikowski Z., Nawrot B.
Biomolecules , 2020
174.
DNA probe modified with 3-iron bis(dicarbollide) for electrochemical determination of DNA sequence of Avian Influenza Virus H5N1
Grabowska I., Stachyra A., Góra-Sochacka A., Sirko A., Olejniczak A.B., Leśnikowski Z.J., Radecki J., Radecka H.
Biosensors and Bioelectronics , 2014
175.
A convenient approach towards boron cluster modifications with adenosine and 2′-deoxyadenosine
Semioshkin A., Bregadze V., Godovikov I., Ilinova A., Lesnikowski Z.J., Lobanova I.
Journal of Organometallic Chemistry , 2011
176.
New boron-containing 2′-deoxyadenosines
Ilinova A.A., Bregadze V.I., Bogomazova A.N., Lobanova I.A., Mironov A.F., Semioshkin A.A.
Russian Chemical Bulletin , 2013
177.
Molecular Recognition of Modified Adenine Nucleotides by the P2Y1-Receptor. 1. A Synthetic, Biochemical, and NMR Approach
Halbfinger E., Major D.T., Ritzmann M., Ubl J., Reiser G., Boyer J.L., Harden K.T., Fischer B.
Journal of Medicinal Chemistry , 1999
178.
Synthesis of the first conjugates of 5-ethynyl-2′-deoxyuridine with closo-dodecaborate and cobalt-bis-dicarbollide boron clusters
Semioshkin A., Ilinova A., Lobanova I., Bregadze V., Paradowska E., Studzińska M., Jabłońska A., Lesnikowski Z.J.
Tetrahedron , 2013
179.
Synthesis, cytotoxicity and antiviral activity studies of the conjugates of cobalt bis(1,2-dicarbollide)(-I) with 5-ethynyl-2′-deoxyuridine and its cyclic derivatives
Ilinova A., Semioshkin A., Lobanova I., Bregadze V.I., Mironov A.F., Paradowska E., Studzińska M., Jabłońska A., Białek-Pietras M., Leśnikowski Z.J.
Tetrahedron , 2014
180.
rcr_90_7_785bib180
Korshun
Russ. J. Bioorg. Chem. , 1997
183.
Advances in Tumor Targeted Liposomes
Jain A., Jain S.K.
Current Molecular Medicine , 2018
184.
rcr_90_7_785bib184
Nakamura
2012
185.
rcr_90_7_785bib185
Schaffran
2008
186.
Dodecaborate cluster lipids with variable headgroups for boron neutron capture therapy: Synthesis, physical–chemical properties and toxicity
Schaffran T., Lissel F., Samatanga B., Karlsson G., Burghardt A., Edwards K., Winterhalter M., Peschka-Süss R., Schubert R., Gabel D.
Journal of Organometallic Chemistry , 2009
187.
Synthesis of conjugates of closo-dodecaborate dianion with cholesterol using a “click” reaction
Druzina A.A., Zhidkova O.B., Kosenko I.D.
Russian Chemical Bulletin , 2020
189.
Synthesis of dodecaborate-conjugated cholesterols for efficient boron delivery in neutron capture therapy
Nakamura H., Ueno M., Lee J., Ban H.S., Justus E., Fan P., Gabel D.
Tetrahedron Letters , 2007
190.
Boron-Containing Lipids and Liposomes: New Conjugates of Cholesterol with Polyhedral Boron Hydrides.
Bregadze V.I., Sivaev I.B., Dubey R.D., Semioshkin A., Shmal'ko A.V., Kosenko I.D., Lebedeva K.V., Mandal S., Sreejyothi P., Sarkar A., Shen Z., Wu A., Hosmane N.S.
Chemistry - A European Journal , 2020
191.
rcr_90_7_785bib191
Shmal’ko
Usp. Khim. Khim. Tekhnol. , 2013
192.
Interaction of Fluorescently Substituted Metallacarboranes with Cyclodextrins and Phospholipid Bilayers: Fluorescence and Light Scattering Study
Uchman M., Jurkiewicz P., Cígler P., Grüner B., Hof M., Procházka K., Matějíček P.
Langmuir , 2010
193.
Fluorescent BODIPY-Anionic Boron Cluster Conjugates as Potential Agents for Cell Tracking.
Chaari M., Gaztelumendi N., Cabrera-González J., Peixoto-Moledo P., Viñas C., Xochitiotzi-Flores E., Farfán N., Ben Salah A., Nogués C., Núñez R.
Bioconjugate Chemistry , 2018
194.
Organotin Dyes Bearing Anionic Boron Clusters as Cell-Staining Fluorescent Probes
Muñoz-Flores B.M., Cabrera-González J., Viñas C., Chávez-Reyes A., Dias H.V., Jiménez-Pérez V.M., Núñez R.
Chemistry - A European Journal , 2018
195.
Small-Molecule Kinase-Inhibitors-Loaded Boron Cluster as Hybrid Agents for Glioma-Cell-Targeting Therapy.
Couto M., Mastandrea I., Cabrera M., Cabral P., Teixidor F., Cerecetto H., Viñas C.
Chemistry - A European Journal , 2017
196.
Closo-Carboranyl- and Metallacarboranyl [1,2,3]triazolyl-Decorated Lapatinib-Scaffold for Cancer Therapy Combining Tyrosine Kinase Inhibition and Boron Neutron Capture Therapy
Couto M., Alamón C., García M., Kovacs M., Trias E., Nievas S., Pozzi E., Curotto P., Thorp S., Dagrosa M., Teixidor F., Viñas C., Cerecetto H.
Cells , 2020
197.
Bimodal Therapeutic Agents Against Glioblastoma, One of the Most Lethal Forms of Cancer
Couto M., Alamón C., Nievas S., Perona M., Dagrosa M.A., Teixidor F., Cabral P., Viñas C., Cerecetto H.
Chemistry - A European Journal , 2020