Colchitaxel, a coupled compound made from microtubule inhibitors colchicine and paclitaxel

Karunananda Bombuwala, Thomas Kinstle, Vladimir Popik, Sonal O. Uppal, James B. Olesen, Jose Viña and Carol A. Heckman
Beilstein J. Org. Chem. 2006, 2, No. 13. https://doi.org/10.1186/1860-5397-2-13

Supporting Information

Supporting Information File 1: Attached Proton Test: Spectrum of Attached Proton Test.
Format: JPEG Size: 1.3 MB Download
Supporting Information File 2: Mass Spectrum: Spectrum from Electron Spray Ionization Mass Spectrometry.
Format: JPEG Size: 1.4 MB Download
Supporting Information File 3: Proton NMR: Spectrum from Proton Nuclear Magnetic Resonance.
Format: JPEG Size: 1.2 MB Download
Supporting Information File 4: VRO showing microtubule + ends localized by antibody against EB1 in a control cell. Part of the VRO is rendered in a two-dimensional form in Figure 2. Control cells were treated with solvent vehicle only. Note that + ends of microtubules at the cell edge are elongated and point downward toward the substratum. The frame is 74 μm wide.
Format: MOV Size: 8.9 MB Download
Supporting Information File 5: VRO showing microtubule + ends localized by antibody against EB1 in a colchitaxel-treated cell. Part of the VRO is rendered in the two-dimensional form in Figure 3. Note that + ends of microtubules at the cell edge appear blunt and rough, and EB1 distribution is occasionally discontinuous. The frame is 63 μm wide.
Format: MOV Size: 9.3 MB Download
Supporting Information File 6: High-resolution MS of colchicine.
Format: PDF Size: 11.3 KB Download
Supporting Information File 7: High-resolution MS of paclitaxel. (Top) Spectrum of starting material. (Bottom) Theoretical spectrum of paclitaxel sodium salt
Format: PDF Size: 13.0 KB Download
Supporting Information File 8: Experimental data (DOC) containing all experimental data
Format: DOC Size: 43.5 KB Download

Cite the Following Article

Colchitaxel, a coupled compound made from microtubule inhibitors colchicine and paclitaxel
Karunananda Bombuwala, Thomas Kinstle, Vladimir Popik, Sonal O. Uppal, James B. Olesen, Jose Viña and Carol A. Heckman
Beilstein J. Org. Chem. 2006, 2, No. 13. https://doi.org/10.1186/1860-5397-2-13

How to Cite

Bombuwala, K.; Kinstle, T.; Popik, V.; Uppal, S. O.; Olesen, J. B.; Viña, J.; Heckman, C. A. Beilstein J. Org. Chem. 2006, 2, No. 13. doi:10.1186/1860-5397-2-13

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Kesel, A. J. Novel Antineoplastic Inducers of Mitochondrial Apoptosis in Human Cancer Cells. Molecules (Basel, Switzerland) 2024, 29, 914. doi:10.3390/molecules29040914
  • Nudelman, A. Mutual Prodrugs - Codrugs. Current medicinal chemistry 2023, 30, 4283–4339. doi:10.2174/0929867330666221209102650
  • Zefirov, N. A.; Mamaeva, A. V.; Radchenko, E.; Milaeva, E. R.; Kuznetsov, S. A.; Zefirova, O. N. Conjugate of podophyllotoxin with chlorambucil: synthesis, biological testing and molecular modeling. Biomeditsinskaia khimiia 2021, 67, 289–294. doi:10.18097/pbmc20216703289
  • Škubník, J.; Pavlíčková, V.; Ruml, T.; Rimpelová, S. Current Perspectives on Taxanes: Focus on Their Bioactivity, Delivery and Combination Therapy. Plants (Basel, Switzerland) 2021, 10, 569. doi:10.3390/plants10030569
  • Girola, N.; Resende-Lara, P. T.; Figueiredo, C. R.; Massaoka, M. H.; Azevedo, R. A.; Cunha, R. L. O. R.; Polonelli, L.; Travassos, L. R. Molecular, Biological and Structural Features of VL CDR-1 Rb44 Peptide, Which Targets the Microtubule Network in Melanoma Cells. Frontiers in oncology 2019, 9, 25. doi:10.3389/fonc.2019.00025
  • Kurek, J. Cytotoxic Colchicine Alkaloids: From Plants to Drugs. Cytotoxicity; InTech, 2018. doi:10.5772/intechopen.72622
  • Ghawanmeh, A. A.; Chong, K. F.; Sarkar, S. M.; Abu Bakar, M.; Othaman, R.; Khalid, R. M. Colchicine prodrugs and codrugs: Chemistry and bioactivities. European journal of medicinal chemistry 2017, 144, 229–242. doi:10.1016/j.ejmech.2017.12.029
  • Dubey, K. K.; Kumar, P.; Labrou, N. E.; Shukla, P. Biotherapeutic potential and mechanisms of action of colchicine. Critical reviews in biotechnology 2017, 37, 1038–1047. doi:10.1080/07388551.2017.1303804
  • Liu, J.; Pang, Y.; Bhattacharyya, J.; Liu, W.; Weitzhandler, I.; Li, X.; Chilkoti, A. Developing Precisely Defined Drug-Loaded Nanoparticles by Ring-Opening Polymerization of a Paclitaxel Prodrug. Advanced healthcare materials 2016, 5, 1868–1873. doi:10.1002/adhm.201600230
  • Bhattacharyya, J.; Bellucci, J. J.; Weitzhandler, I.; McDaniel, J. R.; Spasojevic, I.; Li, X.; Lin, C.-C.; Ashley, J.-T.; Chilkoti, A. A paclitaxel-loaded recombinant polypeptide nanoparticle outperforms Abraxane in multiple murine cancer models. Nature communications 2015, 6, 7939. doi:10.1038/ncomms8939
  • Vilanova, C.; Díaz-Oltra, S.; Murga, J.; Falomir, E.; Carda, M.; Redondo-Horcajo, M.; Díaz, J. F.; Barasoain, I.; Marco, J. A. Design and synthesis of pironetin analogue/colchicine hybrids and study of their cytotoxic activity and mechanisms of interaction with tubulin. Journal of medicinal chemistry 2014, 57, 10391–10403. doi:10.1021/jm501112q
  • Erfani, M.; Shamsaei, M.; Mohammadbaghery, F.; Shirmardi, S. P. Synthesis and evaluation of a 99mTc-labeled tubulin-binding agent for tumor imaging. Journal of labelled compounds & radiopharmaceuticals 2014, 57, 419–424. doi:10.1002/jlcr.3200
  • Oltra, D.; Clausell, M.; Ventura, F.; Horcajo, R.; Díaz, F.; Barasoain, I.; Marco, A.
  • Nacoulma, A. P.; Megalizzi, V.; Pottier, L.; De Lorenzi, M.; Thoret, S.; Dubois, J.; Vandeputte, O. M.; Duez, P.; Vereecke, D.; Jaziri, M. E. Potent Antiproliferative Cembrenoids Accumulate in Tobacco upon Infection with Rhodococcus fascians and Trigger Unusual Microtubule Dynamics in Human Glioblastoma Cells. PloS one 2013, 8, e77529. doi:10.1371/journal.pone.0077529
  • Lin, P.-C.; Shen, C.-C.; Liao, C.-K.; Jow, G.-M.; Chiu, C.-T.; Chung, T.-H.; Wu, J. C. HYS-32, a novel analogue of combretastatin A-4, enhances connexin43 expression and gap junction intercellular communication in rat astrocytes. Neurochemistry international 2013, 62, 881–892. doi:10.1016/j.neuint.2013.02.027
  • Lourenço, A.; Ferreira, L. M.; Branco, P. S. Molecules of Natural Origin, Semi-synthesis and Synthesis with Anti-Inflammatory and Anticancer Utilities. Current pharmaceutical design 2012, 18, 3979–4046. doi:10.2174/138161212802083644
  • Malysheva, Y. B.; Combes, S.; Allegro, D.; Peyrot, V.; Knochel, P.; Gavryushin, A.; Fedorov, A. Y. Synthesis and biological evaluation of novel anticancer bivalent colchicine-tubulizine hybrids. Bioorganic & medicinal chemistry 2012, 20, 4271–4278. doi:10.1016/j.bmc.2012.05.072
  • Crielaard, B. J.; van der Wal, S.; Le, H. T.; Bode, A.; Lammers, T.; Hennink, W. E.; Schiffelers, R. M.; Fens, M. H.; Storm, G. Liposomes as carriers for colchicine-derived prodrugs: Vascular disrupting nanomedicines with tailorable drug release kinetics. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 2011, 45, 429–435. doi:10.1016/j.ejps.2011.08.027
  • Wardle, N. J.; Kalber, T. L.; Bell, J. D.; Bligh, S. W. A. Synthesis and characterisation of a novel tubulin-directed DO3A-colchicine conjugate with potential theranostic features. Bioorganic & medicinal chemistry letters 2011, 21, 3346–3348. doi:10.1016/j.bmcl.2011.04.014
  • Nicolaus, N.; Zapke, J.; Riesterer, P.; Neudörfl, J.-M.; Prokop, A.; Oschkinat, H.; Schmalz, H.-G. Azides derived from colchicine and their use in library synthesis: A practical entry to new bioactive derivatives of an old natural drug. ChemMedChem 2010, 5, 661–665. doi:10.1002/cmdc.201000063

Patents

  • GELLERMAN GARY; GILAD YOSI; TUCHINSKY HELENA. Anticancer drug conjugates. US 11007271 B2, May 18, 2021.
  • GELLERMAN GARY; GILAD YOSI; TUCHINSKY HELENA. ANTICANCER DRUG CONJUGATES. WO 2017216791 A1, Dec 21, 2017.
  • MALAKHOV MICHAEL P; LI TIEJUN. Microparticle formulations for delivery to the lower and central respiratory tract and methods of manufacture. US 9700602 B2, July 11, 2017.
  • DAVIS MATTHEW W. Colchicine compositions and methods. US 7964647 B2, June 21, 2011.
Other Beilstein-Institut Open Science Activities