Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

• Jorge de Lima Neto and
• Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

• formation of microtubules, which are important structures in the constitution of eukaryotic cells [74]. All tested compounds interfered with the polymerization of tubulin, and when compared to colchicine, classified as a destabilizing agent which prevents the microtubule assembly [55], the tested

• derivatives of compound 2 favor to various degrees the formation of microtubules, suggesting that the mechanism of this class of compound interacts with tubulin in a way to allow the microtubule assembly. The authors also observed that the introduction of higher polarity groups at the position of the double

• . After binding to tubulin, they act as stabilizing agents, allowing the formation of microtubules in the early stages, but preventing their disassembly in the final stages of cell division, thus leading to apoptosis [15][55][74] in a mechanism similar to taxol® [76]. However, it is worth to note that

Using multiple self-sorting for switching functions in discrete multicomponent systems

• Amit Ghosh and
• Michael Schmittel

Beilstein J. Org. Chem. 2020, 16, 2831–2853, doi:10.3762/bjoc.16.233

• cytosine (C) [2]. Similarly, proteins, like microtubules and actin filaments, are self-sorted on the molecular level in living cells [3]. Furthermore, the smaller molecules of life such as sugars [4], peptides, and fatty acids [5] undergo self-sorting in the construction of a cell [6][7]. The above

Recent synthesis of thietanes

• Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

• (Taxotere®) both are anticancer drugs of the taxoid series. They inhibit cell growth through the interaction with microtubules. In order to study the structure–activity relationships, the D-ring-modified deoxythiataxoid 154a was synthesized. For this, the iodomethyloxirane derivative 152 was first treated

Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo

• Alexander Sailer,
• Franziska Ermer,
• Yvonne Kraus,
• Rebekkah Bingham,
• Ferdinand H. Lutter,
• Julia Ahlfeld and
• Oliver Thorn-Seshold

Beilstein J. Org. Chem. 2020, 16, 125–134, doi:10.3762/bjoc.16.14

• microtubules (MTs), which play a pivotal role as a dynamic scaffold for a multitude of cellular processes. These include mechanostasis, the completion of mitosis, cell motility, and cargo trafficking in all cell types, as well as cell-type-specific roles, such as polarization, cargo sorting, and trafficking in

A toolbox of molecular photoswitches to modulate the CXCR3 chemokine receptor with light

• Xavier Gómez-Santacana,
• Sabrina M. de Munnik,
• Tamara A. M. Mocking,
• Niels J. Hauwert,
• Shanliang Sun,
• Prashanna Vijayachandran,
• Iwan J. P. de Esch,
• Henry F. Vischer,
• Maikel Wijtmans and
• Rob Leurs

Beilstein J. Org. Chem. 2019, 15, 2509–2523, doi:10.3762/bjoc.15.244

• activity and physiological events with light. A number of protein targets have been explored with photochromic small-molecule ligands, such as ion channels, microtubules, enzymes and GPCRs (G protein-coupled receptors) [1][10]. We focus our photopharmacology research on GPCRs [3][7][11], which constitute a

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

• Eirinaios I. Vrettos,
• Gábor Mező and
• Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

• utilization of paclitaxel are its high hydrophobicity, requiring suitable vehicles to effectively deliver it to tumor tissues, and the development of multidrug resistance due to the P-glycoprotein-mediated efflux [85][92]. Paclitaxel stabilizes microtubules by binding specifically to the beta-tubulin subunit

• , promoting mitotic halt and consequently cell death [93]. The difference with other known drugs that act on microtubules (vinca alkaloids) is that paclitaxel does not induce the disassembly of microtubules but boosts the polymerization of tubulin [94]. Sites available in PTX for the formation of PDCs are

SF002-96-1, a new drimane sesquiterpene lactone from an Aspergillus species, inhibits survivin expression

• Silke Felix,
• Louis P. Sandjo,
• Till Opatz and
• Gerhard Erkel

Beilstein J. Org. Chem. 2013, 9, 2866–2876, doi:10.3762/bjoc.9.323

• centromere protein (INCENP) and Borealin/Dasra-B. In this complex, survivin promotes mitosis by mediating the segregation of sister chromatids, stabilization of microtubules in late mitosis and acting as an interphase between the centromere/central spindle and the CPC [8][9]. Furthermore, survivin shuttles

Efficient syntheses of 25,26-dihydrodictyostatin and 25,26-dihydro-6-epi-dictyostatin, two potent new microtubule-stabilizing agents

• María Jiménez,
• Wei Zhu,
• Andreas Vogt,
• Billy W. Day and
• Dennis P. Curran

Beilstein J. Org. Chem. 2011, 7, 1372–1378, doi:10.3762/bjoc.7.161

• ; microtubules; NHK; Introduction The discovery of compounds that function as anticancer agents by altering the dynamics of microtubules continues to be an important goal in medicinal chemistry. Such agents can force the cell to exit mitosis aberrantly, leading to apoptosis [1][2]. Important classes of

• paclitaxel, and these data have recently been reported in detail [30]. Briefly, both compounds were potent microtubule-perturbing agents that induced mitotic arrest and microtubule assembly in vitro and in intact cells. Each displaced [3H]paclitaxel and [14C]epothilone B from microtubules with potencies

Self-assembled ordered structures in thin films of HAT5 discotic liquid crystal

• Piero Morales,
• Jan Lagerwall,
• Paolo Vacca,
• Sabine Laschat and
• Giusy Scalia

Beilstein J. Org. Chem. 2010, 6, No. 51, doi:10.3762/bjoc.6.51

• important observation is that the large-scale order is retained. The increase in the temperature range of the ordered state is an effect of the confinement of the molecules into a very thin structure, analogous to the observations made in liquid crystal confined in electrospun polymeric microtubules [14

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, doi:10.1186/1860-5397-2-13

• , colchitaxel (1), had some of the same effects on microtubules as the combination of starting compounds. It also caused shortening and fragmentation of the + end protein cap. Conclusion Since microtubule inhibitor combinations give results unlike those obtained with either inhibitor alone, it is important to

• therefore important for lateral binding between tubulin dimers [11]. The anti-tumor activity of microtubule inhibitors is often attributed to their ability to inhibit cell division. When the cell starts to divide, microtubules are organized into two arrays, each having the - ends associated with one of two

• microtubule organizing centers located near the cell periphery and the + ends located towards the chromosomes. This enables the microtubules to pull the daughter chromosomes apart during mitotic division. However, microtubules also play important roles in organelle transport, cell shape maintenance, and