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Author: Grafiati

Published: 10 December 2022

Last updated: 20 February 2023

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1

Alessio, Enzo, and Luigi Messori. "NAMI-A and KP1019/1339, Two Iconic Ruthenium Anticancer Drug Candidates Face-to-Face: A Case Story in Medicinal Inorganic Chemistry." Molecules 24, no. 10 (May 24, 2019): 1995. http://dx.doi.org/10.3390/molecules24101995.

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NAMI-A ((ImH)[trans-RuCl4(dmso-S)(Im)], Im = imidazole) and KP1019/1339 (KP1019 = (IndH)[trans-RuCl4(Ind)2], Ind = indazole; KP1339 = Na[trans-RuCl4(Ind)2]) are two structurally related ruthenium(III) coordination compounds that have attracted a lot of attention in the medicinal inorganic chemistry scientific community as promising anticancer drug candidates. This has led to a considerable amount of studies on their respective chemico-biological features and to the eventual admission of both to clinical trials. The encouraging pharmacological performances qualified KP1019 mainly as a cytotoxic agent for the treatment of platinum-resistant colorectal cancers, whereas the non-cytotoxic NAMI-A has gained the reputation of being a very effective antimetastatic drug. A critical and strictly comparative analysis of the studies conducted so far on NAMI-A and KP1019 allows us to define the state of the art of these experimental ruthenium drugs in terms of the respective pharmacological profiles and potential clinical applications, and to gain some insight into the inherent molecular mechanisms. Despite their evident structural relatedness, deeply distinct biological and pharmacological profiles do emerge. Overall, these two iconic ruthenium complexes form an exemplary and unique case in the field of medicinal inorganic chemistry.

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2

Heffeter, Petra, Katharina Böck, Bihter Atil, Mir Ali Reza Hoda, Wilfried Körner, Caroline Bartel, Ute Jungwirth, et al. "Intracellular protein binding patterns of the anticancer ruthenium drugs KP1019 and KP1339." JBIC Journal of Biological Inorganic Chemistry 15, no. 5 (March 11, 2010): 737–48. http://dx.doi.org/10.1007/s00775-010-0642-1.

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3

Stultz, Laura K., Alexandra Hunsucker, Sydney Middleton, Evan Grovenstein, Jacob O’Leary, Eliot Blatt, Mary Miller, James Mobley, and Pamela K. Hanson. "Proteomic analysis of the S. cerevisiae response to the anticancer ruthenium complex KP1019." Metallomics 12, no. 6 (2020): 876–90. http://dx.doi.org/10.1039/d0mt00008f.

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4

Bergamo, A., A. Masi, M. A. Jakupec, B. K. Keppler, and G. Sava. "Inhibitory Effects of the Ruthenium Complex KP1019 in Models of Mammary Cancer Cell Migration and Invasion." Metal-Based Drugs 2009 (September 17, 2009): 1–9. http://dx.doi.org/10.1155/2009/681270.

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The effects of indazolium trans-[tetrachlorobis(1H-indazole)ruthenate(III)] (KP1019, or FFC14A), the second ruthenium compound that entered clinical trials, in an in vitro model of tumour invasion and metastasis show that the antitumour effects of this compound might include also the modulation of cell behaviour although its cytotoxicity appears to be predominant over these effects. The comparison with its imidazole analogue KP418 shows however its superiority, being able to control in vitro cell growth and in some instances also in vivo tumour development. These results suggest that the activity of KP1019 is predominantly due to direct cytotoxic effects for tumour cells, evident also in vivo on primary tumour growth and that the effects on modulation of the biological behaviour of the cancer cell can be present but might have only a partial role.

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5

Kuhn, P. S., V. Pichler, A. Roller, M. Hejl, M. A. Jakupec, W. Kandioller, and B. K. Keppler. "Improved reaction conditions for the synthesis of new NKP-1339 derivatives and preliminary investigations on their anticancer potential." Dalton Transactions 44, no. 2 (2015): 659–68. http://dx.doi.org/10.1039/c4dt01645a.

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NKP-1339 and KP1019 derivatives were synthesized under mild reaction settings in high yields. The characterization and influence of the N-alkyl substitution on the aqueous stability, redox potentials, in vitro cytotoxicity and cellular accumulation are discussed.

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6

Cirri, Damiano, Tiziano Marzo, Iogann Tolbatov, Alessandro Marrone, Francesco Saladini, Ilaria Vicenti, Filippo Dragoni, Adele Boccuto, and Luigi Messori. "In Vitro Anti-SARS-CoV-2 Activity of Selected Metal Compounds and Potential Molecular Basis for Their Actions Based on Computational Study." Biomolecules 11, no. 12 (December 10, 2021): 1858. http://dx.doi.org/10.3390/biom11121858.

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Metal-based drugs represent a rich source of chemical substances of potential interest for the treatment of COVID-19. To this end, we have developed a small but representative panel of nine metal compounds, including both synthesized and commercially available complexes, suitable for medical application and tested them in vitro against the SARS-CoV-2 virus. The screening revealed that three compounds from the panel, i.e., the organogold(III) compound Aubipyc, the ruthenium(III) complex KP1019, and antimony trichloride (SbCl3), are endowed with notable antiviral properties and an acceptable cytotoxicity profile. These initial findings prompted us to perform a computational study to unveil the likely molecular basis of their antiviral actions. Calculations evidenced that the metalation of nucleophile sites in SARS-CoV-2 proteins or nucleobase strands, induced by Aubipyc, SbCl3, and KP1019, is likely to occur. Remarkably, we found that only the deprotonated forms of Cys and Sec residues can react favorably with these metallodrugs. The mechanistic implications of these findings are discussed.

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7

Levina, Aviva, Anthony R. M. Chetcuti, and Peter A. Lay. "Controversial Role of Transferrin in the Transport of Ruthenium Anticancer Drugs." Biomolecules 12, no. 9 (September 18, 2022): 1319. http://dx.doi.org/10.3390/biom12091319.

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Ruthenium complexes are at the forefront of developments in metal-based anticancer drugs, but many questions remain open regarding their reactivity in biological media, including the role of transferrin (Tf) in their transport and cellular uptake. A well-known anticancer drug, KP1019 ((IndH)[RuIIICl4(Ind)2], where Ind = indazole) and a reference complex, [RuIII(nta)2]3− (nta = nitrilotriacetato(3−)) interacted differently with human apoTf, monoFeTf, or Fe2Tf. These reactions were studied by biolayer interferometry (BLI) measurements of Ru–Fe–Tf binding to recombinant human transferrin receptor 1 (TfR1) in conjunction with UV-vis spectroscopy and particle size analysis. Cellular Ru uptake in human hepatoma (HepG2) cells was measured under the conditions of the BLI assays. The mode of Tf binding and cellular Ru uptake were critically dependent on the nature of Ru complex, availability of Fe(III) binding sites of Tf, and the presence of proteins that competed for metal binding, particularly serum albumin. Cellular uptake of KP1019 was not Tf-mediated and occurred mostly by passive diffusion, which may also be suitable for treatments of inoperable cancers by intratumoral injections. High cellular Ru uptake from a combination of [RuIII(nta)2]3− and Fe2Tf in the absence of significant Ru–Tf binding was likely to be due to trapping of Ru(III) species into the endosome during TfR1-mediated endocytosis of Fe2Tf.

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8

Juszczak, Michał, Magdalena Kluska, Daniel Wysokiński, and Katarzyna Woźniak. "Anti-cancer properties of ruthenium compounds: NAMI-A and KP1019." Postępy Higieny i Medycyny Doświadczalnej 74 (February 19, 2020): 12–19. http://dx.doi.org/10.5604/01.3001.0013.8549.

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Cancer research is among the key challenges in current medicine and biology. Many decades of investigations have brought measurable benefits in both areas with regard to expanding the knowledge of the molecular mechanism of cancer and developing treatment strategies. Despite that cancers are still among diseases with the highest mortality rate, and cancer treatment is often unsuccessful and connected with severe side effects. The development of therapeutic strategies in both targeting the primary tumor origin and preventing metastasis is largely based on testing newly synthesized chemical agents, including a group of metal-containing complexes. It seems that ruthenium-containing complexes are of high potential in cancer therapy, and our work presents the current data about the application of ruthenium-based complexes − NAMI-A and KP1019 in cancer therapy.

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9

Gransbury, Gemma K., Peter Kappen, Chris J. Glover, James N. Hughes, Aviva Levina, Peter A. Lay, Ian F. Musgrave, and Hugh H. Harris. "Comparison of KP1019 and NAMI-A in tumour-mimetic environments." Metallomics 8, no. 8 (2016): 762–73. http://dx.doi.org/10.1039/c6mt00145a.

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10

Heffeter, P., M. A. Jakupec, M. Pongratz, P. Chiba, M. Micksche, W. Körner, M. Hauses, B. Marian, B. K. Keppler, and W. Berger. "630 Molecular mechanisms of resistance against the ruthenium compound KP1019." European Journal of Cancer Supplements 2, no. 8 (September 2004): 190–91. http://dx.doi.org/10.1016/s1359-6349(04)80638-4.

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11

Heffeter, P., A. Riabtseva, Y. Senkiv, C. R. Kowol, W. Körner, U. Jungwith, N. Mitina, et al. "Nanoformulation Improves Activity of the (pre)Clinical Anticancer Ruthenium Complex KP1019." Journal of Biomedical Nanotechnology 10, no. 5 (May 1, 2014): 877–84. http://dx.doi.org/10.1166/jbn.2014.1763.

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12

Dömötör, Orsolya, Christian G. Hartinger, Anna K. Bytzek, Tamás Kiss, Bernhard K. Keppler, and Eva A. Enyedy. "Characterization of the binding sites of the anticancer ruthenium(III) complexes KP1019 and KP1339 on human serum albumin via competition studies." JBIC Journal of Biological Inorganic Chemistry 18, no. 1 (October 18, 2012): 9–17. http://dx.doi.org/10.1007/s00775-012-0944-6.

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13

Dwyer, Brendan G., Emily Johnson, Efren Cazares, Karen L. McFarlane Holman, and Sarah R. Kirk. "Ruthenium anticancer agent KP1019 binds more tightly than NAMI-A to tRNAPhe." Journal of Inorganic Biochemistry 182 (May 2018): 177–83. http://dx.doi.org/10.1016/j.jinorgbio.2018.02.019.

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14

Jones, Michael R., Changhua Mu, Michael C. P. Wang, Michael I. Webb, Charles J. Walsby, and Tim Storr. "Modulation of the Aβ peptide aggregation pathway by KP1019 limits Aβ-associated neurotoxicity." Metallomics 7, no. 1 (2015): 129–35. http://dx.doi.org/10.1039/c4mt00252k.

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15

Bartel, Caroline, Alexander E. Egger, Michael A. Jakupec, Petra Heffeter, Markus Galanski, Walter Berger, and Bernhard K. Keppler. "Influence of ascorbic acid on the activity of the investigational anticancer drug KP1019." JBIC Journal of Biological Inorganic Chemistry 16, no. 8 (June 26, 2011): 1205–15. http://dx.doi.org/10.1007/s00775-011-0809-4.

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16

Singh, Vikash, Gajendra Kumar Azad, Amarendar Reddy M., Shivani Baranwal, and Raghuvir S. Tomar. "Anti-cancer drug KP1019 induces Hog1 phosphorylation and protein ubiquitylation in Saccharomyces cerevisiae." European Journal of Pharmacology 736 (August 2014): 77–85. http://dx.doi.org/10.1016/j.ejphar.2014.04.032.

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17

Jakupec, M. A., V. B. Arion, S. Kapitza, E. Reisner, A. Eichinger, M. Pongratz, B. Marian, N. Graf v. Keyserlingk, and B. K. Keppler. "KP1019 (FFC14A) from bench to bedside: preclinical and early clinical development ? an overview." Int. Journal of Clinical Pharmacology and Therapeutics 43, no. 12 (December 1, 2005): 595–96. http://dx.doi.org/10.5414/cpp43595.

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18

Singh, Vikash, Gajendra Kumar Azad, Papita Mandal, M. Amarendar Reddy, and Raghuvir S. Tomar. "Anti-cancer drug KP1019 modulates epigenetics and induces DNA damage response inSaccharomyces cerevisiae." FEBS Letters 588, no. 6 (February 20, 2014): 1044–52. http://dx.doi.org/10.1016/j.febslet.2014.02.017.

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19

Cetinbas, Naniye, Michael I. Webb, Joshua A. Dubland, and Charles J. Walsby. "Serum-protein interactions with anticancer Ru(III) complexes KP1019 and KP418 characterized by EPR." JBIC Journal of Biological Inorganic Chemistry 15, no. 2 (August 26, 2009): 131–45. http://dx.doi.org/10.1007/s00775-009-0578-5.

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20

Śpiewak, Klaudyna, Sylwia Świątek, Barbara Jachimska, and Małgorzata Brindell. "Induction of transferrin aggregation by indazolium [tetrachlorobis(1H-indazole)ruthenate(iii)] (KP1019) and its biological function." New Journal of Chemistry 43, no. 28 (2019): 11296–306. http://dx.doi.org/10.1039/c9nj01342c.

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21

Fischer, Britta, Petra Heffeter, Kushtrim Kryeziu, Lars Gille, Samuel M. Meier, Walter Berger, Christian R. Kowol, and Bernhard K. Keppler. "Poly(lactic acid) nanoparticles of the lead anticancer ruthenium compound KP1019 and its surfactant-mediated activation." Dalton Trans. 43, no. 3 (2014): 1096–104. http://dx.doi.org/10.1039/c3dt52388h.

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22

Lentz, Frederike, Anne Drescher, Andreas Lindauer, Magdalena Henke, Ralf A. Hilger, Christian G. Hartinger, Max E. Scheulen, Christian Dittrich, Bernhard K. Keppler, and Ulrich Jaehde. "Pharmacokinetics of a novel anticancer ruthenium complex (KP1019, FFC14A) in a phase I dose-escalation study." Anti-Cancer Drugs 20, no. 2 (February 2009): 97–103. http://dx.doi.org/10.1097/cad.0b013e328322fbc5.

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23

Bierle, Lindsey A., Kira L. Reich, Braden E. Taylor, Eliot B. Blatt, Sydney M. Middleton, Shawnecca D. Burke, Laura K. Stultz, Pamela K. Hanson, Janet F. Partridge, and Mary E. Miller. "DNA Damage Response Checkpoint Activation Drives KP1019 Dependent Pre-Anaphase Cell Cycle Delay in S. cerevisiae." PLOS ONE 10, no. 9 (September 16, 2015): e0138085. http://dx.doi.org/10.1371/journal.pone.0138085.

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24

Golla, Upendarrao, Swati Swagatika, Sakshi Chauhan, and Raghuvir Singh Tomar. "A systematic assessment of chemical, genetic, and epigenetic factors influencing the activity of anticancer drug KP1019 (FFC14A)." Oncotarget 8, no. 58 (September 30, 2017): 98426–54. http://dx.doi.org/10.18632/oncotarget.21416.

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25

Richert, Monika, Grzegorz Trykowski, Mariusz Walczyk, Marcin J. Cieślak, Julia Kaźmierczak-Barańska, Karolina Królewska-Golińska, Janusz W. Sobczak, and Stanisław Biniak. "Modification of multiwalled carbon nanotubes with a ruthenium drug candidate—indazolium[tetrachlorobis(1H-indazole)ruthenate(iii)] (KP1019 )." Dalton Transactions 49, no. 46 (2020): 16791–800. http://dx.doi.org/10.1039/d0dt03528a.

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26

Aitken, Jade B., Sumy Antony, Claire M. Weekley, Barry Lai, Leone Spiccia, and Hugh H. Harris. "Distinct cellular fates for KP1019 and NAMI-A determined by X-ray fluorescence imaging of single cells." Metallomics 4, no. 10 (2012): 1051. http://dx.doi.org/10.1039/c2mt20072d.

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27

Kapitza, Susanne, Michael A. Jakupec, Maria Uhl, Bernhard K. Keppler, and Brigitte Marian. "The heterocyclic ruthenium(III) complex KP1019 (FFC14A) causes DNA damage and oxidative stress in colorectal tumor cells." Cancer Letters 226, no. 2 (August 2005): 115–21. http://dx.doi.org/10.1016/j.canlet.2005.01.002.

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28

Shah, Pramod Kumar, and P. K. Shukla. "A DFT study of reactions of Ru(III) anticancer drug KP1019 with 8-oxoguanine and 8-oxoadenine." Structural Chemistry 31, no. 5 (June 16, 2020): 2087–92. http://dx.doi.org/10.1007/s11224-020-01563-3.

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29

Büchel, Gabriel E., Iryna N. Stepanenko, Michaela Hejl, Michael A. Jakupec, Bernhard K. Keppler, and Vladimir B. Arion. "En Route to Osmium Analogues of KP1019: Synthesis, Structure, Spectroscopic Properties and Antiproliferative Activity oftrans-[OsIVCl4(Hazole)2]." Inorganic Chemistry 50, no. 16 (August 15, 2011): 7690–97. http://dx.doi.org/10.1021/ic200728b.

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30

Hartinger, C. G., S. Hann, G. Koellensperger, M. Sulyok, M. Groessl, A. R. Timerbaev, A. V. Rudnev, G. Stingeder, and B. K. Keppler. "Interactions of a novel ruthenium-based anticancer drug (KP1019 or FFC14a) with serum proteins ? significance for the patient." Int. Journal of Clinical Pharmacology and Therapeutics 43, no. 12 (December 1, 2005): 583–85. http://dx.doi.org/10.5414/cpp43583.

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31

Motswainyana, William M., and Peter A. Ajibade. "Anticancer Activities of Mononuclear Ruthenium(II) Coordination Complexes." Advances in Chemistry 2015 (February 19, 2015): 1–21. http://dx.doi.org/10.1155/2015/859730.

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Ruthenium compounds are highly regarded as potential drug candidates. The compounds offer the potential of reduced toxicity and can be tolerated in vivo. The various oxidation states, different mechanism of action, and the ligand substitution kinetics of ruthenium compounds give them advantages over platinum-based complexes, thereby making them suitable for use in biological applications. Several studies have focused attention on the interaction between active ruthenium complexes and their possible biological targets. In this paper, we review several ruthenium compounds which reportedly possess promising cytotoxic profiles: from the discovery of highly active compounds imidazolium [trans-tetrachloro(dmso)(imidazole)ruthenate(III)] (NAMI-A), indazolium [trans-tetrachlorobis(1H-indazole)ruthenate(III)](KP1019), and sodium trans-[tetrachloridobis(1H-indazole)ruthenate(III)] (NKP-1339) to the recent work based on both inorganic and organometallic ruthenium(II) compounds. Half-sandwich organometallic ruthenium complexes offer the opportunity of derivatization at the arene moiety, while the three remaining coordination sites on the metal centre can be functionalised with various coordination groups of various monoligands. It is clear from the review that these mononuclear ruthenium(II) compounds represent a strongly emerging field of research that will soon culminate into several ruthenium based antitumor agents.

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32

Stevens, Shannon K., Amy P. Strehle, Rebecca L. Miller, Sarah H. Gammons, Kyle J. Hoffman, John T. McCarty, Mary E. Miller, Laura K. Stultz, and Pamela K. Hanson. "The Anticancer Ruthenium Complex KP1019 Induces DNA Damage, Leading to Cell Cycle Delay and Cell Death in Saccharomyces cerevisiae." Molecular Pharmacology 83, no. 1 (October 22, 2012): 225–34. http://dx.doi.org/10.1124/mol.112.079657.

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33

Kuhn, Paul-Steffen, Gabriel E. Büchel, Katarina K. Jovanović, Lana Filipović, Siniša Radulović, Peter Rapta, and Vladimir B. Arion. "Osmium(III) Analogues of KP1019: Electrochemical and Chemical Synthesis, Spectroscopic Characterization, X-ray Crystallography, Hydrolytic Stability, and Antiproliferative Activity." Inorganic Chemistry 53, no. 20 (October 7, 2014): 11130–39. http://dx.doi.org/10.1021/ic501710k.

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34

Heffeter, P., M. Pongratz, E. Steiner, P. Chiba, M. A. Jakupec, L. Elbling, B. Marian, et al. "Intrinsic and Acquired Forms of Resistance against the Anticancer Ruthenium Compound KP1019 [Indazolium trans-[tetrachlorobis(1H-indazole)ruthenate (III)] (FFC14A)." Journal of Pharmacology and Experimental Therapeutics 312, no. 1 (August 26, 2004): 281–89. http://dx.doi.org/10.1124/jpet.104.073395.

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35

Hartinger, Christian G, Michael A Jakupec, Stefanie Zorbas-Seifried, Michael Groessl, Alexander Egger, Walter Berger, Haralabos Zorbas, Paul J Dyson, and Bernhard K Keppler. "KP1019, A New Redox-Active Anticancer Agent - Preclinical Development and Results of a Clinical Phase I Study in Tumor Patients." Chemistry & Biodiversity 5, no. 10 (October 2008): 2140–55. http://dx.doi.org/10.1002/cbdv.200890195.

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36

Avramovic, Natasa, Nikola Ignjatovic, and Aleksandar Savic. "Platinum and ruthenium complexes as promising molecules in cancer therapy." Srpski arhiv za celokupno lekarstvo 147, no. 1-2 (2019): 105–9. http://dx.doi.org/10.2298/sarh180706075a.

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Cancer is one of the most common fatal diseases in humans nowadays. About 20 million new cancer cases are expected in the next two decades worldwide. The development of new chemotherapeutic agents with improved properties is presently the main challenge in the medicinal chemistry. Cisplatin was introduced to oncology in 1978 as first chemotherapeutic agent regarding its specific interaction with DNA, leading to its damage and causing the cell death. Since the first application of cisplatin in cancer therapy, there has been a growing interest in new metal-based compounds, in particular platinum and ruthenium complexes, with better anticancer activity and less side-effects compared to cisplatin. Carboplatin and oxaliplatin have shown promising action against some types of cancer, which are resistant to cisplatin. With the aim to overcome cross-resistance to these Pt(II) drugs, bioavailable platinum complexes (satraplatin and picoplatin) firstly found application as orally administered drugs, as well as some combined therapies of Pt(II) drugs (cisplatin, picoplatin) with specific resistant modulators. In recent years, novel polymer and liposomal formulations of platinum drugs (prolindac, lipoplatin, lipoxal, aroplatin) have been designed with strategy to improve drug delivery to target cancer cells and reduce toxicity. Complexes based on ruthenium have great potential to become leading candidates for the medical use in anticancer therapy. Some of these compounds have shown good anticancer activity, both in vitro and in vivo and two of them (KP1019 and NAMI-A) have passed clinical trials and given promising results.

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37

Ferraro, Maria Grazia, Marialuisa Piccolo, Gabriella Misso, Francesco Maione, Daniela Montesarchio, Michele Caraglia, Luigi Paduano, Rita Santamaria, and Carlo Irace. "Breast Cancer Chemotherapeutic Options: A General Overview on the Preclinical Validation of a Multi-Target Ruthenium(III) Complex Lodged in Nucleolipid Nanosystems." Cells 9, no. 6 (June 5, 2020): 1412. http://dx.doi.org/10.3390/cells9061412.

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In this review we have showcased the preclinical development of original amphiphilic nanomaterials designed for ruthenium-based anticancer treatments, to be placed within the current metallodrugs approach leading over the past decade to advanced multitarget agents endowed with limited toxicity and resistance. This strategy could allow for new options for breast cancer (BC) interventions, including the triple-negative subtype (TNBC) with poor therapeutic alternatives. BC is currently the second most widespread cancer and the primary cause of cancer death in women. Hence, the availability of novel chemotherapeutic weapons is a basic requirement to fight BC subtypes. Anticancer drugs based on ruthenium are among the most explored and advanced next-generation metallotherapeutics, with NAMI-A and KP1019 as two iconic ruthenium complexes having undergone clinical trials. In addition, many nanomaterial Ru complexes have been recently conceived and developed into anticancer drugs demonstrating attractive properties. In this field, we focused on the evaluation of a Ru(III) complex—named AziRu—incorporated into a suite of both zwitterionic and cationic nucleolipid nanosystems, which proved to be very effective for the in vivo targeting of breast cancer cells (BBC). Mechanisms of action have been widely explored in the context of preclinical evaluations in vitro, highlighting a multitarget action on cell death pathways which are typically deregulated in neoplasms onset and progression. Moreover, being AziRu inspired by the well-known NAMI-A complex, information on non-nanostructured Ru-based anticancer agents have been included in a precise manner.

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38

Chang, Stephanie W., Andrew R. Lewis, Kathleen E. Prosser, John R. Thompson, Margarita Gladkikh, Marcel B. Bally, Jeffrey J. Warren, and Charles J. Walsby. "CF3Derivatives of the Anticancer Ru(III) Complexes KP1019, NKP-1339, and Their Imidazole and Pyridine Analogues Show Enhanced Lipophilicity, Albumin Interactions, and Cytotoxicity." Inorganic Chemistry 55, no. 10 (May 4, 2016): 4850–63. http://dx.doi.org/10.1021/acs.inorgchem.6b00359.

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39

Hartinger, Christian G., Stefanie Zorbas-Seifried, Michael A. Jakupec, Bernd Kynast, Haralabos Zorbas, and Bernhard K. Keppler. "From bench to bedside – preclinical and early clinical development of the anticancer agent indazolium trans-[tetrachlorobis(1H-indazole)ruthenate(III)] (KP1019 or FFC14A)." Journal of Inorganic Biochemistry 100, no. 5-6 (May 2006): 891–904. http://dx.doi.org/10.1016/j.jinorgbio.2006.02.013.

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40

Pongratz, Martina, Petra Schluga, Michael A. Jakupec, Vladimir B. Arion, Christian G. Hartinger, G�nter Allmaier, and Bernhard K. Keppler. "Transferrin binding and transferrin-mediated cellular uptake of the ruthenium coordination compound KP1019, studied by means of AAS, ESI-MS and CD spectroscopy." Journal of Analytical Atomic Spectrometry 19, no. 1 (2004): 46. http://dx.doi.org/10.1039/b309160k.

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41

Hummer, Alfred A., Petra Heffeter, Walter Berger, Martin Filipits, David Batchelor, Gabriel E. Büchel, Michael A. Jakupec, Bernhard K. Keppler, and Annette Rompel. "X-ray Absorption Near Edge Structure Spectroscopy to Resolve the in Vivo Chemistry of the Redox-Active Indazolium trans-[Tetrachlorobis(1H-indazole)ruthenate(III)] (KP1019)." Journal of Medicinal Chemistry 56, no. 3 (January 31, 2013): 1182–96. http://dx.doi.org/10.1021/jm301648f.

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42

Bučinský, Lukas, Gabriel E. Büchel, Robert Ponec, Peter Rapta, Martin Breza, Jozef Kožíšek, Marian Gall, et al. "On the Electronic Structure ofmer,trans-[RuCl3(1H-indazole)2(NO)], a Hypothetical Metabolite of the Antitumor Drug Candidate KP1019: An Experimental and DFT Study." European Journal of Inorganic Chemistry 2013, no. 14 (April 4, 2013): 2505–19. http://dx.doi.org/10.1002/ejic.201201526.

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Büchel, Gabriel E., Susanne Kossatz, Ahmad Sadique, Peter Rapta, Michal Zalibera, Lukas Bucinsky, Stanislav Komorovsky, et al. "cis-Tetrachlorido-bis(indazole)osmium(iv) and its osmium(iii) analogues: paving the way towards the cis-isomer of the ruthenium anticancer drugs KP1019 and/or NKP1339." Dalton Transactions 46, no. 35 (2017): 11925–41. http://dx.doi.org/10.1039/c7dt02194a.

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Bijelic, Aleksandar, Sarah Theiner, Bernhard K. Keppler, and Annette Rompel. "X-ray Structure Analysis of Indazoliumtrans-[Tetrachlorobis(1H-indazole)ruthenate(III)] (KP1019) Bound to Human Serum Albumin Reveals Two Ruthenium Binding Sites and Provides Insights into the Drug Binding Mechanism." Journal of Medicinal Chemistry 59, no. 12 (June 7, 2016): 5894–903. http://dx.doi.org/10.1021/acs.jmedchem.6b00600.

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Peng, Chunte Sam, Bogdan I. Fedeles, Vipender Singh, Deyu Li, Tiffany Amariuta, John M. Essigmann, and Andrei Tokmakoff. "Two-dimensional IR spectroscopy of the anti-HIV agent KP1212 reveals protonated and neutral tautomers that influence pH-dependent mutagenicity." Proceedings of the National Academy of Sciences 112, no. 11 (March 2, 2015): 3229–34. http://dx.doi.org/10.1073/pnas.1415974112.

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Antiviral drugs designed to accelerate viral mutation rates can drive a viral population to extinction in a process called lethal mutagenesis. One such molecule is 5,6-dihydro-5-aza-2′-deoxycytidine (KP1212), a selective mutagen that induces A-to-G and G-to-A mutations in the genome of replicating HIV. The mutagenic property of KP1212 was hypothesized to originate from its amino–imino tautomerism, which would explain its ability to base pair with either G or A. To test the multiple tautomer hypothesis, we used 2D IR spectroscopy, which offers subpicosecond time resolution and structural sensitivity to distinguish among rapidly interconverting tautomers. We identified several KP1212 tautomers and found that >60% of neutral KP1212 is present in the enol–imino form. The abundant proportion of this traditionally rare tautomer offers a compelling structure-based mechanism for pairing with adenine. Additionally, the pKa of KP1212 was measured to be 7.0, meaning a substantial population of KP1212 is protonated at physiological pH. Furthermore, the mutagenicity of KP1212 was found to increase dramatically at pH <7, suggesting a significant biological role for the protonated KP1212 molecules. Overall, our data reveal that the bimodal mutagenic properties of KP1212 result from its unique shape shifting ability that utilizes both tautomerization and protonation.

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Díaz, Daniel Barón, Anke Neumann, and Habibu Aliyu. "Thermophilic Water Gas Shift Reaction at High Carbon Monoxide and Hydrogen Partial Pressures in Parageobacillus thermoglucosidasius KP1013." Fermentation 8, no. 11 (November 1, 2022): 596. http://dx.doi.org/10.3390/fermentation8110596.

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The facultatively anaerobic Parageobacillus thermoglucosidasius oxidizes carbon monoxide to produce hydrogen via the water gas shift (WGS) reaction. In the current work, we examined the influence of carbon monoxide (CO) and hydrogen (H2) on the WGS reaction in the thermophilic P. thermoglucosidasius by cultivating two hydrogenogenic strains under varying CO and H2 compositions. Microbial growth and dynamics of the WGS reaction were monitored by evaluating parameters such as pressure, headspace composition, metabolic intermediates, pH, and optical density. Our analyses revealed that compared to the previously studied P. thermoglucosidasius strains, the strain KP1013 demonstrated higher CO tolerance and improved WGS reaction kinetics. Under anaerobic conditions, the lag phase before the WGS reaction shortened to 8 h, with KP1013 showing no hydrogen-induced product inhibition at hydrogen partial pressures up to 1.25 bar. The observed lack of product inhibition and the reduced lag phase of the WGS reaction support the possibility of establishing an industrial process for biohydrogen production with P. thermoglucosidasius.

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Egger, Alexander E., Sarah Theiner, Christoph Kornauth, Petra Heffeter, Walter Berger, Bernhard K. Keppler, and Christian G. Hartinger. "Quantitative bioimaging by LA-ICP-MS: a methodological study on the distribution of Pt and Ru in viscera originating from cisplatin- and KP1339-treated mice." Metallomics 6, no. 9 (2014): 1616–25. http://dx.doi.org/10.1039/c4mt00072b.

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Hu, Hui-Chao, Xin-Sheng Chai, Chun-Yun Zhang, Li-Min Fu, Donald Barnes, Liulian Huang, and Lihui Chen. "Experimental data and kinetic models in terms of methanol formation during oxygen delignification processes of alkaline pulps." Holzforschung 69, no. 8 (October 1, 2015): 933–42. http://dx.doi.org/10.1515/hf-2014-0246.

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Abstract This paper reports on the formation of methanol (MeOH) during conventional oxygen delignification (OD) of four typical alkaline pulps, namely, southern pine kraft pulp (SP-KP), wheat straw soda pulp (WS-SP), and eucalyptus kraft pulp (E-KP) with κ numbers (KN) of 32.8 and 16.9 (E-KP32.8 and E-KP16.9). Based on the mass transfer effect of MeOH and a proposed demethoxylation reaction pathway of lignin, two kinds of kinetic models were proposed to predict MeOH formation. The results show that the two-stage pseudo kinetic model with a first-order rate equation is adequate, which was further modified to a first-order kinetic model by means of which MeOH formation during OD of the pulps can be effectively predicted. Finally, the single set of kinetic parameters for the WS-SP, E-KP32.8, and E-KP16.9 pulps was calculated. The proposed kinetic model is considered as a valuable tool for the prediction and control of MeOH formation during OD of various alkaline pulps.

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Komadel, P., J. Hrobáriková, L’ Smrčok, and B. Koppelhuber-Bitschnau. "Hydration of reduced-charge montmorillonite." Clay Minerals 37, no. 3 (September 2002): 543–50. http://dx.doi.org/10.1180/0009855023730057.

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AbstractA series of reduced-charge montmorillonites with cation exchange capacities of 89, 73, 49 and 29% of the starting mineral was prepared from a Li-saturated smectite (Kriva Palanka, Republic of Macedonia) by heating at 110, 130, 160 and 300°C for 24 h (samples KP110 – KP300, respectively). Hydration properties of this series were investigated gravimetrically and by in situ XRD at different relative humidities (RHs). In the gravimetric experiments, higher water contents were observed for desorption than for sorption and hysteresis was present over the whole range of RHs for all the samples. The parent montmorillonite and the samples KP110 and KP130 retained similar amounts of water under the same conditions, thus showing that the decreased negative charge on the layers had minor effect on the water uptake at all investigated RHs. Significantly decreased water content was retained by KP160 while KP300 contained only 8% water at 100% RH. The d001 values of the parent montmorillonite and the samples KP110 and KP130 increased with RH, while those of KP160 and KP300 were independent of RH and remained at ∼10.4 and ∼9.6 Å, respectively.

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Bailey, Victoria N., Jennifer L. Sones, Caroline M. Camp, and Erin L. Oberhaus. "72 Endocrine and ovarian responses to combined estradiol benzoate-sulpiride in anestrous mares treated with kisspeptin." Journal of Animal Science 98, Supplement_2 (November 1, 2020): 36. http://dx.doi.org/10.1093/jas/skz397.082.

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Abstract The objective of this study was to determine if incorporation of kisspeptin 10 (Kp10) into an estradiol benzoate (EB)-sulpiride treatment would result in greater endocrine responses, and a greater number of mares ovulating within 28 days of treatment compared to EB-sulpiride alone. Eighteen anestrous mares were blocked by horse type (light horse and pony crosses), body condition, and age, then randomly assigned to treatment or control. On day 0, all mares received 50 mg EB. On day 1, mini osmotic pumps containing saline (n = 9) or Kp10 (50 mg/hour; n = 9) were inserted subcutaneously in the neck and remained for 7 days. Serial blood sampling occurred for 24 hours after pump placement. On day 2, all mares received 3 g sulpiride. Serial blood sampling continued for 36 hours and daily for 28 days. Transrectal ultrasounds were performed regularly for detection of ovulation. Plasma was assayed for prolactin, luteinizing hormone (LH) and progesterone. Data were analyzed by ANOVA with repeated measures. Plasma prolactin increased (P < .001) in response to sulpiride in all mares and remained stimulated for 7 days. Prolactin responses tended to be greater (P = .09) in Kp10- treated mares compared to controls. No differences were detected in plasma LH during the first 24 hours after pump placement; however, LH increased in all mares beginning 5 days after sulpiride and were greater (P < .05) in Kp10-mares from day 7 to day 21. Eleven of 18 (61%) mares ovulated within 18 days of sulpiride treatment; however, no differences in ovulation dates were detected between Kp10 treated- and control- mares. No differences were detected in plasma progesterone during the first 5 days post ovulation. In conclusion, incorporation of Kp10 potentiated the prolactin and LH responses to EB-sulpiride, but did not further advance first ovulation in treated-mares.

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