Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


IMPACT FACTOR 2018: 2.350
5-year IMPACT FACTOR: 4.037

CiteScore 2018: 4.66

SCImago Journal Rank (SJR) 2018: 1.240
Source Normalized Impact per Paper (SNIP) 2018: 1.826

Online
ISSN
1365-3075
See all formats and pricing
More options …
Volume 91, Issue 4

Issues

Half- and mixed-sandwich metallacarboranes for potential applications in medicine

Marta GozziORCID iD: https://orcid.org/0000-0001-5170-9085 / Benedikt SchwarzeORCID iD: https://orcid.org/0000-0002-5815-8703 / Evamarie Hey-HawkinsORCID iD: https://orcid.org/0000-0003-4267-0603
Published Online: 2019-01-25 | DOI: https://doi.org/10.1515/pac-2018-0806

Abstract

Today, medicinal chemistry is still clearly dominated by organic chemistry, and commercially available boron-based drugs are rare. In contrast to hydrocarbons, boranes prefer the formation of polyhedral clusters via delocalized 3c2e bonds, such as polyhedral dicarba-closo-dodecaborane(12) (closo-C2B10H12). These clusters have remarkable biological stability, and the three isomers, 1,2- (ortho), 1,7- (meta), and 1,12-dicarba-closo-dodecaborane(12) (para), have attracted much interest due to their unique structural features. Furthermore, anionic nido clusters ([7,8-C2B9H11]2−), derived from the neutral icosahedral closo cluster 1,2-dicarba-closo-dodecaborane(12) by deboronation followed by deprotonation are suitable ligands for transition metals and offer the possibility to form metallacarboranes, for example via coordination through the upper pentagonal face of the cluster. The isolobal analogy between the cyclopentadienyl(–1) ligand (Cp) and [C2B9H11]2− clusters (dicarbollide anion, Cb2−) is the motivation in using Cb2− as ligand for coordination to a metal center to design compounds for various applications. This review focuses on potential applications of half- and mixed-sandwich-type transition metal complexes in medicine.

Keywords: biomedical applications; carboranes; Distinguished Women in Chemistry and Chemical Engineering; medicinal chemistry; metallacarboranes

References

  • [1]

    B. Jones, S. Adams, G. T. Miller, M. I. Jesson, T. Watanabe, B. P. Wallner. Blood 102, 1641 (2003).CrossrefGoogle Scholar

  • [2]

    Bortezomib: B. A. Teicher, G. Ara, R. Herbst, V. J. Palombella, J. Adams. Clin. Cancer Res. 5, 2638 (1999).Google Scholar

  • [3]

    Bortezomib: E. S. Lightcap, T. A. McCormack, C. S. Pien, V. Chau, J. Adams, P. J. Elliott. Clin. Chem. 46, 673 (2000).Google Scholar

  • [4]

    Bortezomib: T. Hideshima, P. Richardson, D. Chauhan, V. J. Palombella, P. J. Elliott, J. Adams, K. C. Anderson. Cancer Res. 61, 3071 (2001).Google Scholar

  • [5]

    Bortezomib: J. Adams, M. Behnke, S. W. Chen, A. A. Cruickshank, L. R. Dick, L. Grenier, J. M. Klunder, Y. T. Ma, L. Plamondon, R. L. Stein. Bioorg. Med. Chem. Lett. 8, 333 (2016).Google Scholar

  • [6]

    Tavaborole (AN2690): S. J. Baker, Y.-K. Zhang, T. Akama, A. Lau, H. Zhou, V. Hernandez, W. Mao, M. R. K. Alley, V. Sanders, J. J. Plattner. J. Med. Chem. 49, 4447 (2006).CrossrefGoogle Scholar

  • [7]

    Tavaborole (AN2690): F. L. Rock, W. Mao, A. Yaremchuk, M. Tukalo, T. Crepin, H. Zhou, Y. K. Zhang, V. Hernandez, T. Akama, S. J. Baker, J. J. Plattner, L. Shapiro, S. A. Martinis, S. J. Benkovic, S. Cusack, M. R. Alley. Science 316, 1759 (2007).CrossrefGoogle Scholar

  • [8]

    Crisaborole (AN2728): Anacor Pharmaceuticals. Crisaborole, https://www.anacor.com/R-and-D/crisaborole (20.10.2016).

  • [9]

    Crisaborole (AN2728): G. B. Bolger. Cell Signal. 7, 706 (2016).Google Scholar

  • [10]

    Crisaborole (AN2728): Z. D. Draelos, L. F. Stein Gold, D. F. Murrell, M. H. Hughes, L. T. Zane. J. Drugs Dermatol. 15, 172 (2016).Google Scholar

  • [11]

    Epetraborole (AN3365): S. J. Baker, V. S. Hernandez, R. Sharma, J. A. Nieman, T. Akama, Y.-K. Zhang, J. J. Plattner, M. R. K. Alley, R. Singh, F. Rock. PCT Int. Appl. WO 2008157726 A1 20081224, Filed 15 October 2008, Issued 22 April 2010; SCYX-7158 (AN5568).Google Scholar

  • [12]

    Epetraborole (AN3365): R. T. Jacobs, B. Nare, S. A. Wring, M. D. Orr, D. Chen, J. M. Sligar, M. X. Jenks, R. A. Noe, T. S. Bowling, L. T. Mercer, C. Rewerts, E. Gaukel, J. Owens, R. Parham, R. Randolph, B. Beaudet, C. J. Bacchi, N. Yarlett, J. J. Plattner, Y. Freund, C. Ding, T. Akama, Y.-K. Zhang, R. Brun, M. Kaiser, I. Scandale, R. Don. PLoS Neglect. Trop. Dis. 5, 1151 (2011).CrossrefGoogle Scholar

  • [13]

    Epetraborole (AN3365): S. Wring, E. Gaukel, B. Nare, R. Jacobs, B. Beaudet, T. Bowling, L. Mercer, C. Bacchi, N. Yarlett, R. Randolph, R. Parham, C. Rewerts, J. Platner, R. Don. Parasitology 141, 104 (2014).CrossrefGoogle Scholar

  • [14]

    R. F. Barth, J. A. Coderre, M. G. Vicente, T. E. Blue. Clin. Cancer Res. 11, 3987 (2005).CrossrefGoogle Scholar

  • [15]

    R. F. Barth, P. Mi, W. Yang. Cancer Commun. 38, 35 (2018).CrossrefGoogle Scholar

  • [16]

    K. Yokoyama, S.-I. Miyatake, Y. Kajimoto, S. Kawabata, A. Doi, T. Yoshida, T. Asano, M. Kirihata, K. Ono, T. Kuroiwa. J. Neurooncol. 78, 227 (2006).CrossrefGoogle Scholar

  • [17]

    R. F. Barth. Appl. Radiat. Isot. 67, S3–S6 (2009).Google Scholar

  • [18]

    M. Driess, H. Nöth. Molecular Clusters of the Main Group Elements, Wiley-VCH Verlag GmbH & Co. KgaA, Weinheim (2004).Google Scholar

  • [19]

    E. D. Jemmis, E. G. Jayasree, P. Parameswaran. Chem. Soc. Rev. 35, 157 (2006).CrossrefGoogle Scholar

  • [20]

    A. M. Spokoyny, C. W. Machan, D. J. Clingerman, M. S. Rosen, M. J. Wiester, R. D. Kennedy, C. L. Stern, A. A. Sarjeant, C. A. Mirkin. Nature Chem. 3, 590 (2011).CrossrefGoogle Scholar

  • [21]

    W. A. G. Sauerwein, A. Wittig, R. Moss, Y. Nakagawa. Neutron Capture Therapy, Principles and Applications, Springer, Berlin (2012).Google Scholar

  • [22]

    N. S. Hosmane. Boron Science: New Technologies and Applications, 1st ed., CRC Press, Boca Raton, FL, USA (2012).Google Scholar

  • [23]

    R. L. Moss. Appl. Radiat. Isot. 88, 2 (2014).CrossrefGoogle Scholar

  • [24]

    V. M. Ahrens, R. Frank, S. Boehnke, C. L. Schütz, G. Hampel, D. S. Iffland, N. H. Bings, E. Hey-Hawkins, A. G. Beck-Sickinger. ChemMedChem 10, 164 (2015).CrossrefGoogle Scholar

  • [25]

    R. Frank, V. M. Ahrens, S. Boehnke, A. G. Beck-Sickinger, E. Hey-Hawkins. ChemBioChem 17, 308 (2016).CrossrefGoogle Scholar

  • [26]

    V. M. Ahrens, R. Frank, S. Stadlbauer, A. G. Beck-Sickinger, E. Hey-Hawkins. J. Med. Chem. 54, 2368 (2011).CrossrefGoogle Scholar

  • [27]

    R. Frank, E. Hey-Hawkins. J. Organomet. Chem. 798, 46 (2016).Google Scholar

  • [28]

    R. Frank, V. M. Ahrens, S. Boehnke, S. Hofmann, M. Kellert, S. Saretz, S. Pandey, M. B. Sárosi, Á. Bartók, A. G. Beck-Sickinger, E. Hey-Hawkins. Pure Appl. Chem. 87, 163 (2015).CrossrefGoogle Scholar

  • [29]

    A. F. Armstrong, J. F. Valliant. Dalton Trans. 4240 (2007).Google Scholar

  • [30]

    C. G. Wermuth, C. R. Ganellin, P. Lindberg, L. A. Mitscher. Pure Appl. Chem. 70, 1129 (1998).CrossrefGoogle Scholar

  • [31]

    F. Issa, M. Kassiou, L. M. Rendina. Chem. Rev. 111, 5701 (2011).CrossrefGoogle Scholar

  • [32]

    Z. J. Leśnikowski. J. Med. Chem. 59, 7738 (2016).CrossrefGoogle Scholar

  • [33]

    W. Neumann, R. Frank, E. Hey-Hawkins. Dalton Trans. 44, 1748 (2015).CrossrefGoogle Scholar

  • [34]

    M. Laube, W. Neumann, M. Scholz, P. Lönnecke, B. Crews, L. J. Marnett, J. Pietzsch, T. Kniess, E. Hey-Hawkins. ChemMedChem 8, 329 (2011).Google Scholar

  • [35]

    W. Neumann, R. Frank, E. Hey-Hawkins. Dalton Trans. 44, 1748 (2015).CrossrefGoogle Scholar

  • [36]

    W. Neumann, S. Xu, M. B. Sárosi, M. S. Scholz, B. C. Crews, K. Ghebreselasie, S. Banerjee, L. J. Marnett, E. Hey-Hawkins. ChemMedChem 11, 175 (2016).CrossrefGoogle Scholar

  • [37]

    S. Fujii, A. Yamada, E. Nakano, Y. Takeuchi, S. Mori, H. Masuno, H. Kagechika. Eur. J. Med. Chem. 84, 264 (2014).CrossrefGoogle Scholar

  • [38]

    V. Gómez-Vallejo, N. Vázquez, K. Babu Gona, M. Puigivila, M. González, E. San Sebastián, A. Martin, J. Llop. J. Label Compd. Radiopharm. 57, 209 (2014).CrossrefGoogle Scholar

  • [39]

    M. Scholz, E. Hey-Hawkins. Chem. Rev. 111, 7035 (2011).CrossrefGoogle Scholar

  • [40]

    M. S. Scholz, G. N. Kaluđerović, H. Kommera, R. Paschke, J. Will, W. S. Sheldrick, E. Hey-Hawkins. Eur. J. Med. Chem. 46, 1131 (2011).CrossrefGoogle Scholar

  • [41]

    M. F. Hawthorne, D. C. Young, T. D. Andrews, D. V. Howe, R. L. Pilling, A. D. Pitts, M. Reintjes, L. F. Warren Jr., P. A. Wegner. J. Am. Chem. Soc. 90, 879 (1968).CrossrefGoogle Scholar

  • [42]

    M. Gozzi, B. Schwarze, E. Hey-Hawkins. “Half- and Mixed-Sandwich Metallacarboranes in Catalysis”, in Boron Chemistry in Organometallics, Catalysis, Materials and Medicine, N. S. Hosmane and R. Eagling (Eds.), pp. 27–80, Imperial College Press/World Scientific Publishing (UK) Ltd. (2018).Google Scholar

  • [43]

    B. Schwarze, M. Gozzi, E. Hey-Hawkins. “Half- and Mixed-Sandwich Transition Metal Dicarbollides and nido-Carboranes(–1) for Medicinal Applications”, in Boron-Based Compounds: Potential and Emerging Applications in Medicine, E. Hey-Hawkins and C. Viñas Teixidor (Eds.), pp. 60–108, John Wiley & Sons Ltd., Hoboken, NJ, USA (2018).Google Scholar

  • [44]

    D. A. Brown, M. O. Fanning, N. J. Fitzpatrick. Inorg. Chem. 17, 1620 (1978).CrossrefGoogle Scholar

  • [45]

    R. Hoffmann. Angew. Chem. Int. Ed. 21, 711 (1982).Google Scholar

  • [46]

    R. Grimes. “Metallacarboranes of the Transition and Lanthanide Elements”, in Carboranes, pp. 711–903, Elsevier, Heidelberg (2016).Google Scholar

  • [47]

    M. Corsini, F. Fabrizi de Biani, P. Zanello. Coord. Chem. Rev. 250, 1351 (2006).CrossrefGoogle Scholar

  • [48]

    R. N. Grimes. Dalton Trans. 44, 5939 (2015).CrossrefGoogle Scholar

  • [49]

    S. M. Gao, N. S. Hosmane. Russ. Chem. Bull. Int. Ed. 63, 788 (2014).CrossrefGoogle Scholar

  • [50]

    B. Dash, R. Satapathy, B. R. Swain, C. S. Mahanta, B. B. Jena, N. S. Hosmane. J. Organomet. Chem. 849–850, 170 (2017).Google Scholar

  • [51]

    P. Farràs, E. J. Juárez-Pérez, M. Lepšík, R. Luque, R. Núñez, F. Teixidor. Chem. Soc. Rev. 41, 3445 (2012).CrossrefGoogle Scholar

  • [52]

    M. Bühl, J. Holub, D. Hnyk, J. Macháček. Organometallics 25, 2173 (2006).CrossrefGoogle Scholar

  • [53]

    M. F. Hawthorne, D. C. Young, P. M. Garrett, D. A. Owen, S. G. Schwerin, F. N. Tebbe, P. A. Wegner. J. Am. Chem. Soc. 90, 862 (1968).CrossrefGoogle Scholar

  • [54]

    M. A. Fox, A. K. Huges, A. L. Johnson, M. A. J. Paterson. Dalton Trans. 2009 (2002).Google Scholar

  • [55]

    M. J. Manning, C. B. Knobler, M. F. Hawthorne. Inorg. Chem. 30, 3598 (1991).Google Scholar

  • [56]

    R. Grimes. “Eleven-Vertex Clusters”, in Carboranes, pp. 184–203, Elsevier, Heidelberg (2016).Google Scholar

  • [57]

    A. R. Genady, J. Tan, M. E. El-Zaria, A. Zlitni, N. Janzen, J. F. Valliant. J. Organomet. Chem. 791, 204 (2015).CrossrefGoogle Scholar

  • [58]

    A. S. Louie, L. E. Harrington, J. F. Valliant. Inorg. Chim. Acta 389, 159 (2012).CrossrefGoogle Scholar

  • [59]

    A. Adamska, A. Rumijowska-Galewicz, A. Ruszczynska, M. Studzinska, A. Jablonska, E. Paradowska, E. Bulska, H. Munier-Lehmann, J. Dziadek, Z. J. Lesnikowski, A. B. Olejniczak. Eur. J. Med. Chem. 121, 71 (2016).CrossrefGoogle Scholar

  • [60]

    A. S. Louie, N. Vasdev, J. F. Valliant. J. Med. Chem. 54, 3360 (2011).CrossrefGoogle Scholar

  • [61]

    M. E. El-Zaria, N. Janzen, M. Blacker, J. F. Valliant. Chem. Eur. J. 18, 11071 (2012).CrossrefGoogle Scholar

  • [62]

    I. Maulana, P. Lönnecke, E. Hey-Hawkins. Inorg. Chem. 48, 8638 (2009).CrossrefGoogle Scholar

  • [63]

    C. Viñas, M. Mar Abad, F. Teixidor, R. Sillanpää, R. Kivekäs. J. Organomet. Chem. 555, 17 (1998).CrossrefGoogle Scholar

  • [64]

    F. Teixidor, C. Viñas, M. Mar Abad, M. Lopez, J. Casabó. Organometallics 12, 3766 (1993).CrossrefGoogle Scholar

  • [65]

    O. Crespo, M. Concepcion Gimeno, P. G. Jones, A. Laguna. J. Chem. Soc. Dalton Trans. 4583 (1996).Google Scholar

  • [66]

    F. Teixidor, C. Viñas, R. Sillanpää, R. Kivekäs, J. Casabó. Inorg. Chem. 33, 2645 (1994).CrossrefGoogle Scholar

  • [67]

    C. Viñas, R. Nuñez, I. Rojo, F. Teixidor, R. Kivekäs, R. Sillanpää. Inorg. Chem. 40, 3259 (2001).CrossrefGoogle Scholar

  • [68]

    A. V. Safronov, F. M. Dolgushin, P. V. Petrovskii, I. T. Chizhevsky. Organometallics 24, 2964 (2005).CrossrefGoogle Scholar

  • [69]

    R. Kaplánek, P. Martásek, B. Grüner, S. Panda, J. Rak, B. S. Siler Masters, V. Král, L. J. Roman. J. Med. Chem. 55, 9541 (2012).CrossrefGoogle Scholar

  • [70]

    P. M. Hawkins, P. A. Jelliss, N. Nonaka, X. Shi, W. A. Banks. JPET 329, 608 (2009).CrossrefGoogle Scholar

  • [71]

    D. G. Pruitt, S. M. Baumann, G. J. Place, A. N. Oyeamalu, E. Sinn, P. A. Jelliss. J. Organomet. Chem. 798, 60 (2015).CrossrefGoogle Scholar

  • [72]

    B. Štíbr, J. Holub, I. Císar̈ová, F. Teixidor, C. Viñas. Inorg. Chim. Acta 245, 129 (1996).CrossrefGoogle Scholar

  • [73]

    R. Grimes. “Carboranes in Medicine”, in Carboranes, pp. 945–951, Elsevier, Heidelberg (2016).Google Scholar

  • [74]

    R. C. Reynolds, S. R. Campbell, R. G. Fairchild, R. L. Kisliuk, P. L. Micca, S. F. Queener, J. M. Riordan, W. D. Sedwick, W. R. Waud, A. K. W. Leung, R. W. Dixon, W. J. Suling, D. W. Borhani. J. Med. Chem. 50, 3283 (2007).CrossrefGoogle Scholar

  • [75]

    V. A. Ol’shevskaya, A. V. Zaitsev, V. N. Luzgina, T. T. Kondratieva, O. G. Ivanov, E. G. Kononova, P. V. Petrovskii, A. F. Mironov, V. N. Kalinin, J. Hofmann, A. A. Shtil. Bioorg. Med. Chem. 14, 109 (2006).CrossrefGoogle Scholar

  • [76]

    W. Tjarks, R. Tiwari, Y. Byun, S. Narayanasamy, R. F. Barth. Chem. Commun. 4978 (2007).Google Scholar

  • [77]

    B. A. Wojtczak, A. B. Olejniczak, L. Wang, S. Eriksson, Z. J. Lesnikowski. Nucleosides Nucleotides Nucleic Acids 32, 571 (2013).CrossrefGoogle Scholar

  • [78]

    Z. Yinghuai, A. T. Peng, K. Carpenter, J. A. Maguire, N. S. Hosmane, M. Takagaki. J. Am. Chem. Soc. 127, 9875 (2005).CrossrefGoogle Scholar

  • [79]

    C. Viñas, F. Teixidor, A. J. Harwood. “Cobaltabisdicarbollide‐based Synthetic Vesicles: From Biological Interaction to in vivo Imaging”, in Boron-Based Compounds: Potential and Emerging Applications in Medicine, E. Hey-Hawkins and C. Viñas Teixidor (Eds.), pp. 159–173, John Wiley & Sons Ltd., Hoboken, NJ, USA (2018).Google Scholar

  • [80]

    R. Grimes. “Carboranes in Medicine”, in Carboranes, pp. 953–957, Elsevier, Heidelberg (2016).Google Scholar

  • [81]

    P. Cígler, M. Kožíšek, P. Řezáčová, J. Brynda, Z. Otwinowski, J. Pokorná, J. Plešek, B. Grüner, L. Dolečková-Marešová, M. Máša, J. Sedláček, J. Bodem, H.-G. Kräusslich, V. Král, J. Konvalinka. PNAS 102, 15394 (2005).CrossrefGoogle Scholar

  • [82]

    I. H. Hall, C. E. Tolmie, B. J. Barnes, M. A. Curtis, J. M. Russell, M. G. Finn, R. N. Grimes. Appl. Organomet. Chem. 14, 108 (2000).CrossrefGoogle Scholar

  • [83]

    W. K. Alderton, C. E. Cooper, R. G. Knowles. Biochem. J. 357, 593 (2001).CrossrefGoogle Scholar

  • [84]

    U. Förstermann, W. C. Sessa. Eur. Heart J. 33, 829 (2012).CrossrefGoogle Scholar

  • [85]

    E. P. Erdal, E. A. Litzinger, J. Seo, Y. Zhu, H. Ji, R. B. Silverman. Curr. Top. Med. Chem. 5, 603 (2005).CrossrefGoogle Scholar

  • [86]

    M. Gozzi, B. Schwarze, M.-B. Sárosi, P. Lönnecke, D. Drača, D. Maksimovi-Ivanić, S. Mihatović, E. Hey-Hawkins. Dalton Trans. 46, 12067 (2017).CrossrefGoogle Scholar

  • [87]

    G. Süss-Fink. Dalton Trans. 39, 1673 (2010).CrossrefGoogle Scholar

  • [88]

    S. H. Van Rijt, P. J. Sadler. Drug. Discov. Today 14, 1089 (2010).Google Scholar

  • [89]

    L. S. Micallef, B. T. Loughrey, P. C. Parsons, M. L. Williams. Organometallics 29, 6237 (2010).CrossrefGoogle Scholar

  • [90]

    K. Chen, X. Chen. Curr. Top. Med. Chem. 10, 1227 (2010).CrossrefGoogle Scholar

  • [91]

    G. J. Kelloff, K. A. Krohn, S. M. Larson, R. Weissleder, D. A. Mankoff, J. M. Hoffman, J. M. Link, K. Z. Guyton, W. C. Eckelman, H. I. Scher, J. O’Shaughnessy, B. D. Cheson, C. C. Sigman, J. L. Tatum, G. Q. Mills, D. C. Sullivan, J. Woodcock. Clin. Cancer Res. 11, 7967 (2005).CrossrefGoogle Scholar

  • [92]

    G. Jaouen, M. Salmain, eds. Bioorganometallic Chemistry: Applications in Drug Discovery, Biocatalysis, and Imaging. Wiley-VCH, Weinheim, Germany (2015).Google Scholar

  • [93]

    N. A. Meanwell. J. Med. Chem. 54, 2529 (2011).CrossrefGoogle Scholar

  • [94]

    R. Grimes. “Carboranes in Medicine”, in Carboranes, pp. 968–972, Elsevier, Heidelberg (2016).Google Scholar

  • [95]

    P. W. Causey, T. R. Besanger, J. F. Valliant. J. Med. Chem. 51, 2833 (2008).CrossrefGoogle Scholar

  • [96]

    M. E. El-Zaria, N. Janzen, J. F. Valliant. Organometallics 31, 5940 (2012).CrossrefGoogle Scholar

  • [97]

    I. Heimbold, A. Drews, R. Syhre, M. Kretzschmar, H.-J. Pietzsch, B. Johannsen. Eur. J. Nucl. Med. 29, 82 (2002).CrossrefGoogle Scholar

  • [98]

    S. S. Jurisson, J. D. Lydon. Chem. Rev. 99, 2205 (1999).CrossrefGoogle Scholar

  • [99]

    K. Schlotter, F. Boeckler, H. Hübner, P. Gmeiner. J. Med. Chem. 48, 3696 (2005).CrossrefGoogle Scholar

  • [100]

    D.-H. Wu, C.-H. Wu, Y.-Z. Li, D.-D. Guo, X.-M. Wang, H. Yan. Dalton Trans. 285 (2009).Google Scholar

  • [101]

    V. W. Pike. Trends Pharmacol. Sci. 30, 431 (2009).CrossrefGoogle Scholar

  • [102]

    E. A. Forster, I. A. Cliffe, D. J. Bill, G. M. Dover, D. Jones, Y. Reilly, A. Fletcher. Eur. J. Pharmacol. 281, 81 (1995).CrossrefGoogle Scholar

About the article

Contributed equally.


Published Online: 2019-01-25

Published in Print: 2019-04-24


Funding Source: Verband der Chemischen Industrie

Award identifier / Grant number: 197021

Funding Source: Sächsisches Staatsministerium für Wissenschaft und Kunst

Award identifier / Grant number: LAU-R-N-11-2-0615

Verband der Chemischen Industrie, Funder Id: 10.13039/100007215, Grant Number: 197021 doctoral grant B.S., Sächsisches Staatsministerium für Wissenschaft und Kunst, Funder Id: 10.13039/501100006114, Grant Number: LAU-R-N-11-2-0615 doctoral grant M.G.


Citation Information: Pure and Applied Chemistry, Volume 91, Issue 4, Pages 563–573, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2018-0806.

Export Citation

©2019 IUPAC & De Gruyter. This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. For more information, please visit: http://creativecommons.org/licenses/by-nc-nd/4.0/.Get Permission

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Amr A. A. Attia, Alexandru Lupan, Radu Silaghi-Dumitrescu, and R. Bruce King
Molecules, 2019, Volume 25, Number 1, Page 110
[2]
Marta Gozzi, Benedikt Schwarze, Peter Coburger, and Evamarie Hey-Hawkins
Inorganics, 2019, Volume 7, Number 7, Page 91

Comments (0)

Please log in or register to comment.
Log in