macrocyclic compounds

Summary

Summary: Cyclic compounds with a ring size of approximately 1-4 dozen atoms.

Top Publications

  1. David S, Barros V, Passos Guerra K, Delgado R. Exploring Mycobacterium avium inhibition by macrocyclic compounds. Res Microbiol. 2005;156:904-10 pubmed
    Derivatives of synthetic macrocyclic compounds, MCC, 12- and 14-membered tetraazamacrocycles with N-pendant arms, such as N-methyl (Mepy14), N-acetate (DOTA, TETA and ac3py14) and N-methylphosphonate (DOTP) groups, were investigated in ..
  2. Anderson C, Wadas T, Wong E, Weisman G. Cross-bridged macrocyclic chelators for stable complexation of copper radionuclides for PET imaging. Q J Nucl Med Mol Imaging. 2008;52:185-92 pubmed
    ..This review describes the coordination chemistry and biological behavior of (64)Cu-labeled CB complexes. ..
  3. Harrowven D, Kostiuk S. Macrocylic bisbibenzyl natural products and their chemical synthesis. Nat Prod Rep. 2012;29:223-42 pubmed publisher
    ..Prod. Rep. 1995, 12, 69-75) and largely focuses on new additions to the family and the strategies used to effect their chemical synthesis. ..
  4. Poordad F, Hezode C, Trinh R, Kowdley K, Zeuzem S, Agarwal K, et al. ABT-450/r-ombitasvir and dasabuvir with ribavirin for hepatitis C with cirrhosis. N Engl J Med. 2014;370:1973-82 pubmed publisher
  5. Feld J, Kowdley K, Coakley E, Sigal S, Nelson D, Crawford D, et al. Treatment of HCV with ABT-450/r-ombitasvir and dasabuvir with ribavirin. N Engl J Med. 2014;370:1594-603 pubmed publisher
    ..In this phase 3 trial, we evaluated this regimen in previously untreated patients with HCV genotype 1 infection and no cirrhosis...
  6. Blankson G, Pilch D, Liu A, Liu L, Rice J, LaVoie E. Macrocyclic biphenyl tetraoxazoles: synthesis, evaluation as G-quadruplex stabilizers and cytotoxic activity. Bioorg Med Chem. 2013;21:4511-20 pubmed publisher
    ..These studies provide useful insights into the conformational requirements for the development of selective and more potent G-quadruplex ligands. ..
  7. Ferenci P, Bernstein D, Lalezari J, Cohen D, Luo Y, Cooper C, et al. ABT-450/r-ombitasvir and dasabuvir with or without ribavirin for HCV. N Engl J Med. 2014;370:1983-92 pubmed publisher
    ..We conducted two phase 3 trials to examine the efficacy and safety of this regimen in previously untreated patients with HCV genotype 1 infection and no cirrhosis...
  8. Kowdley K, Lawitz E, Poordad F, Cohen D, Nelson D, Zeuzem S, et al. Phase 2b trial of interferon-free therapy for hepatitis C virus genotype 1. N Engl J Med. 2014;370:222-32 pubmed publisher
  9. Jordan T, Jiang H, Li H, DiMario J. Regulation of skeletal muscle fiber type and slow myosin heavy chain 2 gene expression by inositol trisphosphate receptor 1. J Cell Sci. 2005;118:2295-302 pubmed
    ..The results indicate that IP3R1 activity regulates muscle fiber type-specific gene expression in innervated muscle fibers. ..

More Information

Publications62

  1. Marcaurelle L, Comer E, Dandapani S, Duvall J, Gerard B, Kesavan S, et al. An aldol-based build/couple/pair strategy for the synthesis of medium- and large-sized rings: discovery of macrocyclic histone deacetylase inhibitors. J Am Chem Soc. 2010;132:16962-76 pubmed publisher
    ..The development of stereo-structure/activity relationships was made possible by screening all 16 stereoisomers of the macrolactams produced through the aldol-based B/C/P strategy. ..
  2. Ozaki H, Hori M, Kim Y, Kwon S, Ahn D, Nakazawa H, et al. Inhibitory mechanism of xestospongin-C on contraction and ion channels in the intestinal smooth muscle. Br J Pharmacol. 2002;137:1207-12 pubmed
    ..Xestospongin-C is a selective blocker of the IP(3) receptor in permeabilised cells but not in cells with intact plasma membrane. ..
  3. Minhas G, Pilch D, Kerrigan J, LaVoie E, Rice J. Synthesis and G-quadruplex stabilizing properties of a series of oxazole-containing macrocycles. Bioorg Med Chem Lett. 2006;16:3891-5 pubmed
    ..An unexpected oxidative cleavage reaction afforded a macrocyclic imide that was also evaluated for G-quadruplex stabilizing and cytotoxic activity. ..
  4. Zhao G, Adebiyi A, Blaskova E, Xi Q, Jaggar J. Type 1 inositol 1,4,5-trisphosphate receptors mediate UTP-induced cation currents, Ca2+ signals, and vasoconstriction in cerebral arteries. Am J Physiol Cell Physiol. 2008;295:C1376-84 pubmed publisher
    ..In addition, IP(3)R1 activation constricts cerebral arteries in the absence of SR Ca(2+) release by stimulating plasma membrane I(cat). ..
  5. Montes Navajas P, Corma A, Garcia H. Complexation and fluorescence of tricyclic basic dyes encapsulated in cucurbiturils. Chemphyschem. 2008;9:713-20 pubmed publisher
  6. Jaimovich E, Mattei C, Liberona J, Cardenas C, Estrada M, Barbier J, et al. Xestospongin B, a competitive inhibitor of IP3-mediated Ca2+ signalling in cultured rat myotubes, isolated myonuclei, and neuroblastoma (NG108-15) cells. FEBS Lett. 2005;579:2051-7 pubmed
    ..It is concluded that xestospongin B is an effective cell-permeant, competitive inhibitor of IP(3) receptors in cultured rat myotubes, isolated myonuclei, and neuroblastoma (NG108-15) cells. ..
  7. Johnson J, Kuang S, Misler S, Polonsky K. Ryanodine receptors in human pancreatic beta cells: localization and effects on insulin secretion. FASEB J. 2004;18:878-80 pubmed
  8. Ishima T, Nishimura T, Iyo M, Hashimoto K. Potentiation of nerve growth factor-induced neurite outgrowth in PC12 cells by donepezil: role of sigma-1 receptors and IP3 receptors. Prog Neuropsychopharmacol Biol Psychiatry. 2008;32:1656-9 pubmed publisher
    ..These findings suggest that sigma-1 receptors and interaction with IP3 receptors may be involved in the pharmacological action of donepezil. ..
  9. Monchaud D, Teulade Fichou M. A hitchhiker's guide to G-quadruplex ligands. Org Biomol Chem. 2008;6:627-36 pubmed publisher
    ..The present article aims to help researchers enter this exciting research field, and to highlight recent advances in the design of G-quadruplex ligands. ..
  10. Rzuczek S, Pilch D, Liu A, Liu L, LaVoie E, Rice J. Macrocyclic pyridyl polyoxazoles: selective RNA and DNA G-quadruplex ligands as antitumor agents. J Med Chem. 2010;53:3632-44 pubmed publisher
    ..Compound 19 has significant in vivo anticancer activity against a human breast cancer xenograft (MDA-MB-435) in athymic nude mice. ..
  11. Plaza A, Keffer J, Bifulco G, Lloyd J, Bewley C. Chrysophaentins A-H, antibacterial bisdiarylbutene macrocycles that inhibit the bacterial cell division protein FtsZ. J Am Chem Soc. 2010;132:9069-77 pubmed publisher
  12. Tsai Y, Qi H, Lin C, Lin R, Kerrigan J, Rzuczek S, et al. A G-quadruplex stabilizer induces M-phase cell cycle arrest. J Biol Chem. 2009;284:22535-43 pubmed publisher
    ..In the aggregate, our results suggest that HXDV, which exhibits anti-proliferative and apoptotic activities, is also a novel M-phase blocker, with a mode of action dependent on its G-quadruplex binding activity. ..
  13. Lasseter K, Shaughnessy L, Cummings D, Pezzullo J, Wargin W, Gagnon R, et al. Ghrelin agonist (TZP-101): safety, pharmacokinetics and pharmacodynamic evaluation in healthy volunteers: a phase I, first-in-human study. J Clin Pharmacol. 2008;48:193-202 pubmed publisher
    ..TZP-101 displayed a promising pharmacokinetic, pharmacodynamic, and safety profile for use in gastrointestinal motility disorders. ..
  14. Rzuczek S, Pilch D, LaVoie E, Rice J. Lysinyl macrocyclic hexaoxazoles: synthesis and selective G-quadruplex stabilizing properties. Bioorg Med Chem Lett. 2008;18:913-7 pubmed publisher
    ..Compounds with one valine and one lysine residue display the best combination of G-quadruplex stabilizing ability with no detectable stabilization of duplex DNA. ..
  15. Gregoliński J, Starynowicz P, Hua K, Lunkley J, Muller G, Lisowski J. Helical lanthanide(III) complexes with chiral nonaaza macrocycle. J Am Chem Soc. 2008;130:17761-73 pubmed publisher
  16. Arai M, Ishida S, Setiawan A, Kobayashi M. Haliclonacyclamines, tetracyclic alkylpiperidine alkaloids, as anti-dormant mycobacterial substances from a marine sponge of Haliclona sp. Chem Pharm Bull (Tokyo). 2009;57:1136-8 pubmed
    ..The 22-hydroxy group in 1 was found to reduce anti-mycobacterial activity, because 22-hydroxyhaliclonacyclamine B (1) exhibited weaker anti-microbial activities against Mycobacterium bacilli with MICs in the ranges of 12.5-50 microg/ml. ..
  17. Johnson J, Misler S. Nicotinic acid-adenine dinucleotide phosphate-sensitive calcium stores initiate insulin signaling in human beta cells. Proc Natl Acad Sci U S A. 2002;99:14566-71 pubmed
    ..These data reveal the complexity of insulin signal transduction and function in human beta cells and demonstrate functional NAADP-sensitive Ca(2+) stores in a human primary cultured cell type. ..
  18. Morita H, Tomizawa Y, Tsuchiya T, Hirasawa Y, Hashimoto T, Asakawa Y. Antimitotic activity of two macrocyclic bis(bibenzyls), isoplagiochins A and B from the Liverwort Plagiochila fruticosa. Bioorg Med Chem Lett. 2009;19:493-6 pubmed publisher
    ..The presence of two aromatic rings which can be connected through two atoms bridge spacer of double bond may serve to maintain the backbone conformation...
  19. Khakshoor O, Demeler B, Nowick J. Macrocyclic beta-sheet peptides that mimic protein quaternary structure through intermolecular beta-sheet interactions. J Am Chem Soc. 2007;129:5558-69 pubmed
  20. Tse B, Snyder T, Shen Y, Liu D. Translation of DNA into a library of 13,000 synthetic small-molecule macrocycles suitable for in vitro selection. J Am Chem Soc. 2008;130:15611-26 pubmed publisher
    ..The quality and structural diversity of this expanded DNA-templated library provides a rich starting point for the discovery of functional synthetic small-molecule macrocycles. ..
  21. Shirude P, Gillies E, Ladame S, Godde F, Shin ya K, Huc I, et al. Macrocyclic and helical oligoamides as a new class of G-quadruplex ligands. J Am Chem Soc. 2007;129:11890-1 pubmed
  22. Zheng J, Liu C, Sawaya M, Vadla B, Khan S, Woods R, et al. Macrocyclic ?-sheet peptides that inhibit the aggregation of a tau-protein-derived hexapeptide. J Am Chem Soc. 2011;133:3144-57 pubmed publisher
    ..This model provides a provocative and appealing target for future inhibitor design. ..
  23. Liu C, Sawaya M, Cheng P, Zheng J, Nowick J, Eisenberg D. Characteristics of amyloid-related oligomers revealed by crystal structures of macrocyclic ?-sheet mimics. J Am Chem Soc. 2011;133:6736-44 pubmed publisher
  24. Tsuboi T, Da Silva Xavier G, Holz G, Jouaville L, Thomas A, Rutter G. Glucagon-like peptide-1 mobilizes intracellular Ca2+ and stimulates mitochondrial ATP synthesis in pancreatic MIN6 beta-cells. Biochem J. 2003;369:287-99 pubmed
    ..Taken together, these results demonstrate that GLP-1 potentiates glucose-stimulated insulin release in part via the mobilization of intracellular Ca(2+), and the stimulation of mitochondrial ATP synthesis. ..
  25. Popescu I, Fleshner P, Pezzullo J, Charlton P, Kosutic G, Senagore A. The Ghrelin agonist TZP-101 for management of postoperative ileus after partial colectomy: a randomized, dose-ranging, placebo-controlled clinical trial. Dis Colon Rectum. 2010;53:126-34 pubmed publisher
  26. Eltit J, Hidalgo J, Liberona J, Jaimovich E. Slow calcium signals after tetanic electrical stimulation in skeletal myotubes. Biophys J. 2004;86:3042-51 pubmed
    ..Long-lasting, IP(3)-generated slow calcium signals appear to be a physiological response to activity-related fluctuations in membrane potential sensed by the DHPR. ..
  27. Gordienko D, Bolton T. Crosstalk between ryanodine receptors and IP(3) receptors as a factor shaping spontaneous Ca(2+)-release events in rabbit portal vein myocytes. J Physiol. 2002;542:743-62 pubmed
  28. Fraser G, Venkova K, Hoveyda H, Thomas H, Greenwood Van Meerveld B. Effect of the ghrelin receptor agonist TZP-101 on colonic transit in a rat model of postoperative ileus. Eur J Pharmacol. 2009;604:132-7 pubmed publisher
  29. Driggers E, Hale S, Lee J, Terrett N. The exploration of macrocycles for drug discovery--an underexploited structural class. Nat Rev Drug Discov. 2008;7:608-24 pubmed publisher
  30. Yan H, Li Z, Guo Z, Lu Z, Wang F, Wu L. Effective and reversible DNA condensation induced by bifunctional molecules containing macrocyclic polyamines and naphthyl moieties. Bioorg Med Chem. 2012;20:801-8 pubmed publisher
    ..Cytotoxicity assay showed that the presence of triazole moieties can result in lower toxicity. ..
  31. Jiang J, Sun B, Wang Y, Cui M, Zhang L, Cui C, et al. Synthesis of macrocyclic bisbibenzyl derivatives and their anticancer effects as anti-tubulin agents. Bioorg Med Chem. 2012;20:2382-91 pubmed publisher
    ..The remarkable biological profile and novel structure of these bisbibenzyl derivatives make them possible as promising candidates for clinical development as chemotherapeutic agents. ..
  32. Wang C, Yu M, Kyle A, Jakubec P, Dixon D, Schrock R, et al. Efficient and selective formation of macrocyclic disubstituted Z alkenes by ring-closing metathesis (RCM) reactions catalyzed by Mo- or W-based monoaryloxide pyrrolide (MAP) complexes: applications to total syntheses of epilachnene, yuzu lactone, amb. Chemistry. 2013;19:2726-40 pubmed publisher
    ..3) Polycyclic structures can be accessed without significant isomerization at the existing Z alkenes within the molecule. ..
  33. Kennedy R, Machan C, McGuirk C, Rosen M, Stern C, Sarjeant A, et al. General strategy for the synthesis of rigid weak-link approach platinum(II) complexes: tweezers, triple-layer complexes, and macrocycles. Inorg Chem. 2013;52:5876-88 pubmed publisher
    ..The structures of the complexes may be toggled between semiopen (with only one chelating ligand) and fully closed (with both ligands chelating) via the abstraction and addition of chloride. ..
  34. Ma X, Zhao Y. Biomedical Applications of Supramolecular Systems Based on Host-Guest Interactions. Chem Rev. 2015;115:7794-839 pubmed publisher
  35. Jiang M, Ferdani R, Shokeen M, Anderson C. Comparison of two cross-bridged macrocyclic chelators for the evaluation of 64Cu-labeled-LLP2A, a peptidomimetic ligand targeting VLA-4-positive tumors. Nucl Med Biol. 2013;40:245-51 pubmed publisher
  36. Niess F, Sauvage J. Synthesis of a metal-free coordinating ring via formation of a cleavable [2]catenane. Chem Commun (Camb). 2013;49:10790-2 pubmed publisher
    ..Release of the cleavable ring leads to the formation of the target macrocycle in quantitative yield. ..
  37. Mulla K, Shaik H, Thompson D, Zhao Y. TTFV-based molecular tweezers and macrocycles as receptors for fullerenes. Org Lett. 2013;15:4532-5 pubmed publisher
    ..These compounds were investigated as receptors for fullerenes (C60 and C70) by UV-vis absorption and fluorescence spectroscopy. ..
  38. Chen H, Jiao W, Jones M, Coxon J, Morton J, Bickerstaffe R, et al. New tripeptide-based macrocyclic calpain inhibitors formed by N-alkylation of histidine. Chem Biodivers. 2012;9:2473-84 pubmed publisher
    ..The relative activities are linked to the ability of the component macrocycles to mimic a ?-strand geometry that is known to favor active-site binding. This ability is defined by conformational searches and docking studies with calpain. ..
  39. Fan Q, Lin Y, Hahn F, Jin G. Host-guest capability of a three-dimensional heterometallic macrocycle. Dalton Trans. 2018;47:2240-2246 pubmed publisher
    ..However, macrocyclic compounds with larger cavity sizes, which form 1 : 1 stoichiometry assemblies with a naphthalene ..
  40. Walsh C, O Brien R, Khosla C. Nonproteinogenic amino acid building blocks for nonribosomal peptide and hybrid polyketide scaffolds. Angew Chem Int Ed Engl. 2013;52:7098-124 pubmed publisher
  41. Lee J, Heo S, Lee S, Ko J, Kim H, Kim H. Probing conformational changes of ubiquitin by host-guest chemistry using electrospray ionization mass spectrometry. J Am Soc Mass Spectrom. 2013;24:21-9 pubmed publisher
    ..Furthermore, this provides a direction for designing function-controllable supramolecular system comprising proteins and synthetic host molecules. ..
  42. Gonçalves S, Fernandes A, Oliveira N, Marques J, Costa J, Cabral M, et al. Cytotoxic effects of cadmium in mammary epithelial cells: protective role of the macrocycle [15]pyN5. Food Chem Toxicol. 2012;50:2180-7 pubmed publisher
    ..Protective effects were observed in terms of cell viability, cell proliferation and morphological alterations, being the protection mostly attributed to a chelating-based mechanism. ..
  43. Collins J, Farley K, Limberakis C, Liras S, Price D, James K. Macrocyclizations for medicinal chemistry: synthesis of druglike macrocycles by high-concentration Ullmann coupling. J Org Chem. 2012;77:11079-90 pubmed publisher
    ..A range of substitution patterns and ring sizes are tolerated, and the method has been exemplified by the synthesis of a set of druglike macrocycles. ..
  44. Leventer Roberts M, Hammerman A, Brufman I, Hoshen M, Braun M, Ashur Y, et al. Effectiveness of dasabuvir/ombitasvir/paritaprevir/ritonavir for hepatitis C virus in clinical practice: A population-based observational study. PLoS ONE. 2017;12:e0176858 pubmed publisher
    ..8% among those tested. Treatment with dasabuvir/ombitasvir/paritaprevir/ritonavir demonstrated a near universal effectiveness in achieving a sustained virological response among HCV patients in a large cohort. ..
  45. Rose T, Lawson K, Harran P. Large ring-forming alkylations provide facile access to composite macrocycles. Chem Sci. 2015;6:2219-2223 pubmed publisher
    b>Macrocyclic compounds have potential to enable drug discovery for protein targets with extended, solvent-exposed binding sites...
  46. Dorazio S, Tsitovich P, Siters K, Spernyak J, Morrow J. Iron(II) PARACEST MRI contrast agents. J Am Chem Soc. 2011;133:14154-6 pubmed publisher
    ..CEST imaging using a MRI scanner shows that the CEST effect can be observed in solutions containing low millimolar concentrations of complex at neutral pH, 100 mM NaCl, 20 mM buffer at 25 °C or 37 °C. ..
  47. Devarajan A, Grijalva V, Bourquard N, Meriwether D, Imaizumi S, Shin B, et al. Macrophage paraoxonase 2 regulates calcium homeostasis and cell survival under endoplasmic reticulum stress conditions and is sufficient to prevent the development of aggravated atherosclerosis in paraoxonase 2 deficiency/apoE-/- mice on a Western di. Mol Genet Metab. 2012;107:416-27 pubmed publisher
    ..Our data suggest that macrophage PON2 modulates mechanisms that link ER stress, mitochondrial dysfunction and the development of atherosclerosis. ..
  48. Vinay Kumar B, Bhojya Naik H, Girija D, Sharath N, Pradeepa S, Joy Hoskeri H, et al. Synthesis, DNA-binding, DNA-photonuclease profiling and antimicrobial activity of novel tetra-aza macrocyclic Ni(II), Co(II) and Cu(II) complexes constrained by thiadiazole. Spectrochim Acta A Mol Biomol Spectrosc. 2012;94:192-9 pubmed publisher
    ..The photo induced cleavage studies revealed that the complexes possess photonuclease property against pUC19 DNA under UV-visible irradiation. ..
  49. Ganapati S, Zavalij P, Eikermann M, Isaacs L. In Vitro selectivity of an acyclic cucurbit[n]uril molecular container towards neuromuscular blocking agents relative to commonly used drugs. Org Biomol Chem. 2016;14:1277-87 pubmed publisher
  50. Wintgens V, Le Coeur C, Amiel C, Guigner J, Harangozó J, Miskolczy Z, et al. 4-Sulfonatocalix[6]arene-induced aggregation of ionic liquids. Langmuir. 2013;29:7682-8 pubmed publisher
    ..Cryo-TEM experiments showed dense particles generally with spherical shape and multilayered structure, which has been confirmed by small-angle neutron scattering. ..
  51. Wang X, Ma X, Yang Z, Zhang Z, Wen J, Geng Z, et al. An NBD-armed tetraaza macrocyclic lysosomal-targeted fluorescent probe for imaging copper(II) ions. Chem Commun (Camb). 2013;49:11263-5 pubmed publisher
    ..The probe was specifically localized in lysosomes and successfully applied to visualize Cu(2+) as well as to monitor Cu(2+) level changes in the lysosomes of living cells. ..
  52. Badri P, Dutta S, Wang H, Podsadecki T, Polepally A, Khatri A, et al. Drug Interactions with the Direct-Acting Antiviral Combination of Ombitasvir and Paritaprevir-Ritonavir. Antimicrob Agents Chemother. 2016;60:105-14 pubmed publisher
    ..Ketoconazole, digoxin, pravastatin, and rosuvastatin require lower doses, and omeprazole may require a higher dose. No dose adjustment is required for the 2D regimen. ..
  53. Dow M, Marchetti F, Abrahams K, Vaz L, Besra G, Warriner S, et al. Modular Synthesis of Diverse Natural Product-Like Macrocycles: Discovery of Hits with Antimycobacterial Activity. Chemistry. 2017;23:7207-7211 pubmed publisher
    ..The biological relevance of the chemical space explored was demonstrated through the discovery of a series of macrocycles with significant antimycobacterial activity. ..