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Search for "targeting" in Full Text gives 219 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Synthesis and photophysical studies of a multivalent photoreactive RuII-calix[4]arene complex bearing RGD-containing cyclopentapeptides

  • Sofia Kajouj,
  • Lionel Marcelis,
  • Alice Mattiuzzi,
  • Adrien Grassin,
  • Damien Dufour,
  • Pierre Van Antwerpen,
  • Didier Boturyn,
  • Eric Defrancq,
  • Mathieu Surin,
  • Julien De Winter,
  • Pascal Gerbaux,
  • Ivan Jabin and
  • Cécile Moucheron

Beilstein J. Org. Chem. 2018, 14, 1758–1768, doi:10.3762/bjoc.14.150

Graphical Abstract
  • is also faced by complexes anchored on cell-penetrating peptides. In order to provide a selective cell targeting, we developed a multivalent system composed of a photoreactive ruthenium(II) complex tethered to a calix[4]arene platform bearing multiple RGD-containing cyclopentapeptides. Extensive
  • , once incorporated into targeted cancer cells thanks to the multivalent platform. Keywords: anticancer drug; calixarene; cell targeting; RGD peptide; ruthenium complex; Introduction Long-living luminescent polyazaaromatic ruthenium(II) complexes are intensively studied in a biological context, in
  • of the complex [38]. It should be noted that modifications of ligands to make the resulting complexes more lipophilic or the conjugation of a complex to a CPP do not provide any control on the way these complexes will be internalized by cells and prevent thus any targeting of malignant cells over
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Published 16 Jul 2018

Natural and redesigned wasp venom peptides with selective antitumoral activity

  • Marcelo D. T. Torres,
  • Gislaine P. Andrade,
  • Roseli H. Sato,
  • Cibele N. Pedron,
  • Tania M. Manieri,
  • Giselle Cerchiaro,
  • Anderson O. Ribeiro,
  • Cesar de la Fuente-Nunez and
  • Vani X. Oliveira Jr.

Beilstein J. Org. Chem. 2018, 14, 1693–1703, doi:10.3762/bjoc.14.144

Graphical Abstract
  • low as 12.5 μmol L−1 for the selective targeting of MCF-7 breast cancer cells. Flow cytometry assays further revealed that treatment with wild-type (WT) peptide Dec-NH2 led to necrosis of MCF-7 cells. Additional atomic force microscopy (AFM) measurements indicated that the roughness of cancer cell
  • therapies because of their potential for selectively targeting cancer cells without harm to normal counterparts [37][38][39]. Membrane phospholipids confer permeability to the cell and regulate the flux of metabolites between the extracellular environment and the intracellular content [40]. The membrane of
  • cancer cells is typically negatively charged due to a higher expression of anionic molecules such as phosphatidylserines, and negatively charged glycoproteins and glycosaminoglycans [22][23]. Here, we devised a strategy to exploit the negatively charged environment of cancer cells by targeting it with
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Published 06 Jul 2018

Drug targeting to decrease cardiotoxicity – determination of the cytotoxic effect of GnRH-based conjugates containing doxorubicin, daunorubicin and methotrexate on human cardiomyocytes and endothelial cells

  • Livia Polgár,
  • Eszter Lajkó,
  • Pál Soós,
  • Orsolya Láng,
  • Marilena Manea,
  • Béla Merkely,
  • Gábor Mező and
  • László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 1583–1594, doi:10.3762/bjoc.14.136

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  • Chemistry, Pázmány P. stny 1/A, Hungarian Academy of Science, Budapest, 1117, Hungary 10.3762/bjoc.14.136 Abstract Background: Cardiomyopathy induced by the chemotherapeutic agents doxorubicin and daunorubicin is a major limiting factor for their application in cancer therapy. Chemotactic drug targeting
  • : cardiotoxicity; drug targeting; GnRH-conjugates; HCM; HUVEC; impedimetry; Introduction Gonadotropin-releasing hormone (GnRH) is a peptide hormone secreted by the hypothalamus, which stimulates the release of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the pituitary. Thus, it represents
  • . Small peptides that recognize target receptors on tumor cells might be suitable targeting moieties for this purpose. Hormone peptides, in particular, GnRH and somatostatin derivatives that possess antiproliferative effect on their own, are among the best candidates as homing peptides [10]. A.V. Schally
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Published 28 Jun 2018

Design and biological characterization of novel cell-penetrating peptides preferentially targeting cell nuclei and subnuclear regions

  • Anja Gronewold,
  • Mareike Horn and
  • Ines Neundorf

Beilstein J. Org. Chem. 2018, 14, 1378–1388, doi:10.3762/bjoc.14.116

Graphical Abstract
  • ) with selective suborganelle-targeting properties. The nuclear localization sequence N50, as well as the nucleoli-targeting sequence NrTP, respectively, were fused to a shortened version of the cell-penetrating peptide sC18. We examined cellular uptake, subcellular fate and cytotoxicity of these novel
  • excluded. However, initial drug delivery studies demonstrated the high versatility of these new peptides as efficient transport vectors targeting specifically nuclei and nucleoli. In future, they could be further explored as parts of newly created peptide–drug conjugates. Keywords: anticancer drugs; cell
  • nuclei; cell-penetrating peptides; nucleoli; subcellular targeting; Introduction Various drugs act on targets that are located within the nucleus, the control center of the eukaryotic cell. A lipid bilayer membrane, which is perforated with nuclear pore complex structures through which the transfer of
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Published 07 Jun 2018

Acyl-group specificity of AHL synthases involved in quorum-sensing in Roseobacter group bacteria

  • Lisa Ziesche,
  • Jan Rinkel,
  • Jeroen S. Dickschat and
  • Stefan Schulz

Beilstein J. Org. Chem. 2018, 14, 1309–1316, doi:10.3762/bjoc.14.112

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  • enzyme PgaI2 from P. inhibens, competition experiments were performed. Targeting the optimal chain length of the fully saturated substrates first, a mixture with equal molar concentrations of the substrates 10a–h was offered to the recombinant protein. GC/MS analysis of the resulting extract (Figure 2A
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Published 05 Jun 2018

Novel unit B cryptophycin analogues as payloads for targeted therapy

  • Eduard Figueras,
  • Adina Borbély,
  • Mohamed Ismail,
  • Marcel Frese and
  • Norbert Sewald

Beilstein J. Org. Chem. 2018, 14, 1281–1286, doi:10.3762/bjoc.14.109

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  • glycol spacer with a terminal azide results in a complete loss of activity. Docking studies of the novel cryptophycin analogues to β-tubulin provided a rationale for the observed cytotoxicities. Keywords: cryptophycin; cytotoxic agents; novel payloads; tubulin inhibitors; tumour targeting; Introduction
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Published 01 Jun 2018

Synthetic avenues towards a tetrasaccharide related to Streptococcus pneumonia of serotype 6A

  • Aritra Chaudhury,
  • Mana Mohan Mukherjee and
  • Rina Ghosh

Beilstein J. Org. Chem. 2018, 14, 1095–1102, doi:10.3762/bjoc.14.95

Graphical Abstract
  • conjugate in proper amounts for future vaccine development can only be met via chemical synthesis. Therefore, a number of syntheses targeting the SPn 6A tetrasaccharide has been reported in literature. Initial reports of a linear synthesis were made by Vliegenthart et al. in the nineties [17][18][19][20][21
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Published 17 May 2018

An overview of recent advances in duplex DNA recognition by small molecules

  • Sayantan Bhaduri,
  • Nihar Ranjan and
  • Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

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  • phase synthetic approach for the syntheses of cyclic Py/Im polyamides [84]. This group previously optimized and reported a machine-assisted Fmoc solid phase synthesis of simpler polyamides to afford high step-wise coupling yield [85]. A seven-member library of cyclic polyamides targeting androgen
  • response element (ARE) and the estrogen response element (ERE) was synthesized in 12–17% overall yield. Selective modifications could also be done on the GABA turn units, which showed improved cellular uptake properties. Sugiyama et al. designed and synthesized a series of telomere-targeting synthetically
  • telomere foci clearly because of their fluorescent nature. Later on, the authors successfully designed tandem tetramer Py–Im polyamides with 4 hairpins and 3 hinges targeting 24 bp of the human telomere sequences [88]. Thus, the authors set the new record for the longest binding site of synthetic, non
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Published 16 May 2018

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

Graphical Abstract
  • intervention, radiation and chemotherapy. Drugs used for this purpose are inevitably cytotoxic in order to eliminate cancer cells, but they lack selectivity that could be developed through targeting malignant cells (Figure 1). Due to the uncontrolled peripheral toxicity, anticancer drugs usually kill healthy
  • prodrug with enhanced plasma stability and/or cell permeability [27] and in the same time diminished toxicity for normal cells; c) covalent attachment of a drug on a tumor-targeting element (small molecule, peptide or antibody) able to selectively target and permeate cancer cells. The conjugation is being
  • conducted via a rationally designed linker able to release the drug inside the cancer microenvironment [19]. The ideal targeting molecular device would consist of the following modules: a) the cytotoxic agent (drug), b) the transporting - drug delivery vehicle (i.e., lipid, mannan [28][29][30]), c) the
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Published 26 Apr 2018

Development of novel cyclic NGR peptide–daunomycin conjugates with dual targeting property

  • Andrea Angelo Pierluigi Tripodi,
  • Szilárd Tóth,
  • Kata Nóra Enyedi,
  • Gitta Schlosser,
  • Gergely Szakács and
  • Gábor Mező

Beilstein J. Org. Chem. 2018, 14, 911–918, doi:10.3762/bjoc.14.78

Graphical Abstract
  • selectivity to CD13+ cells. However, the cellular uptake and cytotoxic effect of Dau=Aoa-GFLGK(c[NleNGRE]-GG-)-NH2 was higher in comparison to the control especially on HT-29 cells. Therefore, this conjugate is more suitable for drug targeting with dual targeting property. Keywords: antitumor activity; drug
  • [NleNGRE]-GG)-NH2 conjugate is more suitable for drug targeting with dual acting propensity than our control lead compound. Experimental Synthesis of the novel peptide–drug conjugates Linear precursor peptides were prepared on Rink-Amide MBHA resin by SPPS. Standard Fmoc protected amino acids (Iris Biotech
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Published 25 Apr 2018

Synthesis and in vitro biochemical evaluation of oxime bond-linked daunorubicin–GnRH-III conjugates developed for targeted drug delivery

  • Sabine Schuster,
  • Beáta Biri-Kovács,
  • Bálint Szeder,
  • Viktor Farkas,
  • László Buday,
  • Zsuzsanna Szabó,
  • Gábor Halmos and
  • Gábor Mező

Beilstein J. Org. Chem. 2018, 14, 756–771, doi:10.3762/bjoc.14.64

Graphical Abstract
  • Debrecen, 4032 Debrecen, Hungary 10.3762/bjoc.14.64 Abstract Gonadotropin releasing hormone-III (GnRH-III), a native isoform of the human GnRH isolated from sea lamprey, specifically binds to GnRH receptors on cancer cells enabling its application as targeting moieties for anticancer drugs. Recently, we
  • cellular uptake of the bioconjugates were strongly affected by the amino acid exchange which in turn had an impact on the antitumor activity of the bioconjugates. Keywords: cytostatic effect; daunorubicin; drug-targeting; GnRH derivatives; oxime linkage; Introduction Cancer is one of the most serious
  • receptors (GnRH-R) [1]. Therefore, these peptides are suitable for specific drug targeting to tumor cells. The native ligand of this receptor is GnRH-I (
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Published 04 Apr 2018

Investigations towards the stereoselective organocatalyzed Michael addition of dimethyl malonate to a racemic nitroalkene: possible route to the 4-methylpregabalin core structure

  • Denisa Vargová,
  • Rastislav Baran and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2018, 14, 553–559, doi:10.3762/bjoc.14.42

Graphical Abstract
  • stereoselective synthesis of bioactive compounds [1][2][3]. In particular, stereoselective conversions of nitro compounds served in many syntheses of pharmaceuticals [4]. Derivatives of γ-aminobutyric acid are an important class of medicines targeting problems with the central nervous system, such as pains
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Published 05 Mar 2018

Stimuli-responsive oligonucleotides in prodrug-based approaches for gene silencing

  • Françoise Debart,
  • Christelle Dupouy and
  • Jean-Jacques Vasseur

Beilstein J. Org. Chem. 2018, 14, 436–469, doi:10.3762/bjoc.14.32

Graphical Abstract
  • enzymolabile phosphotriester groups, namely, t-Bu-SATE, OH-SATE and a conjugable aldehyde A-SATE for conjugation to delivery and targeting domains, have been selected for complete evaluation (Scheme 9A, 9B, and 9C, respectively). The optimum phosphotriester placement and number of phosphotriester groups were
  • noncytotoxic fashion. Next, the authors prepared conjugates of the siRNNs via one A-SATE phosphotriester with a hepatocyte-specific tris-N-acetylgalactosamine targeting domain and demonstrated a stronger RNAi response in mouse liver (following subcutaneous or intravenous administration) than the same
  • targeting the nuclease resistance of the ON prodrug. On the other hand, the thermosensitive groups are more suitable for the protection of the thiophosphates flanking the CpG motif of DNA prodrugs to provide both lipophilicity (better cellular uptake) and hydrophilicity (better solubility once groups are
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Published 19 Feb 2018

Synthesis and biological evaluation of RGD and isoDGR peptidomimetic-α-amanitin conjugates for tumor-targeting

  • Lizeth Bodero,
  • Paula López Rivas,
  • Barbara Korsak,
  • Torsten Hechler,
  • Andreas Pahl,
  • Christoph Müller,
  • Daniela Arosio,
  • Luca Pignataro,
  • Cesare Gennari and
  • Umberto Piarulli

Beilstein J. Org. Chem. 2018, 14, 407–415, doi:10.3762/bjoc.14.29

Graphical Abstract
  • , cyclo[DKP-RGD]-Val-Ala-PTX 5 and cyclo[DKP-isoDGR]-Val-Ala-PTX 6). Their tumor targeting ability was assessed in vitro in antiproliferative assays comparing an αVβ3 positive with an αVβ3 negative cell line [29][30]. The cyclo[DKP-isoDGR]-Val-Ala-PTX conjugate 6 displayed a remarkable targeting index (TI
  • antibody α-amanitin conjugates for which the increase of cytotoxicity is 100–100000 times [5]. Therefore, despite the remarkable progresses that have been realized in recent years, integrin targeting SMDCs are still far from the clinic. Experimental Functionalized ligands H2NCH2-cyclo[DKP-RGD] (2) and
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Published 14 Feb 2018

Fluorogenic PNA probes

  • Tirayut Vilaivan

Beilstein J. Org. Chem. 2018, 14, 253–281, doi:10.3762/bjoc.14.17

Graphical Abstract
  • (Figure 3) [33], dsRNA [34], and other unusual structures, such as G-quadruplexes [35], makes PNA an ideal tool for targeting structured nucleic acid targets. Simple fluorescent-labeled PNA probes have found extensive applications in nucleic acid detection and quantitation. Examples of such assays that
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Published 29 Jan 2018

Polarization spectroscopy methods in the determination of interactions of small molecules with nucleic acids – tutorial

  • Tamara Šmidlehner,
  • Ivo Piantanida and
  • Gennaro Pescitelli

Beilstein J. Org. Chem. 2018, 14, 84–105, doi:10.3762/bjoc.14.5

Graphical Abstract
  • alternating or homo-base sequences as well as single-stranded homo-polynucleotides. Such synthetic DNA or RNA have well-defined structural properties and therefore are recommended for studies of small molecules targeting structural DNA or RNA selectivity. All polynucleotides should be dissolved exactly as
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Published 08 Jan 2018

Microfluidic radiosynthesis of [18F]FEMPT, a high affinity PET radiotracer for imaging serotonin receptors

  • Thomas Lee Collier,
  • Steven H. Liang,
  • J. John Mann,
  • Neil Vasdev and
  • J. S. Dileep Kumar

Beilstein J. Org. Chem. 2017, 13, 2922–2927, doi:10.3762/bjoc.13.285

Graphical Abstract
  • serotonin-targeting radiopharmaceuticals was recently reviewed by Paterson et al. [1] and their conclusion was that “the development of PET and single-photon emission computed tomography (SPECT) radioligands to image serotonergic targets is of high interest, and successful evaluation in humans is leading to
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Published 29 Dec 2017

Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays

  • Marco Russo,
  • Daniele La Corte,
  • Annalisa Pisciotta,
  • Serena Riela,
  • Rosa Alduina and
  • Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271

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  • knowledge, the possible inclusion of a generic guest/drug molecule into CD derivatives bearing amine groups have been studied only occasionally [41][43][44][45][46][47][48]. Moreover, the interaction of polycationic CDs with polynucleotides has been mainly considered by targeting their abilities in gene
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Published 18 Dec 2017

Exploring mechanochemistry to turn organic bio-relevant molecules into metal-organic frameworks: a short review

  • Vânia André,
  • Sílvia Quaresma,
  • João Luís Ferreira da Silva and
  • M. Teresa Duarte

Beilstein J. Org. Chem. 2017, 13, 2416–2427, doi:10.3762/bjoc.13.239

Graphical Abstract
  • mechanochemical processes towards attaining metallopharmaceuticals, metallodrugs and MOFs synthesized within our group [49], and another on the design, screening, and characterization of BioMOFs in general [110]. To the best of our knowledge, this is the first short review targeting on the mechanochemical
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Published 14 Nov 2017

Phosphonic acid: preparation and applications

  • Charlotte M. Sevrain,
  • Mathieu Berchel,
  • Hélène Couthon and
  • Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

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  • bone targeting, for the design of supramolecular or hybrid materials, for the functionalization of surfaces, for analytical purposes, for medical imaging or as phosphoantigen. These applications are covering a large panel of research fields including chemistry, biology and physics thus making the
  • 14, Figure 4), was assessed to complex indium [86] or terbium [87] with the aim to develop bone targeting and dosimetry. It was also employed to complex 89Y and applied as pH sensitive NMR probe [88], or as organic precursor of crystalline manganese, nickel [89] or lanthanide-containing hybrid
  • develop bone targeting which was assessed for therapy [96] and imaging [97][98]. Finally, the phosphonic acid group was also employed to immobilize organic or organometallic molecules on the surface of metal oxide [99][100] (Al2O3 [101], TiO2 [102][103], SnO2 [104], Fe3O4 [105], ZnO [106]), CdSe quantum
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Published 20 Oct 2017

18-Hydroxydolabella-3,7-diene synthase – a diterpene synthase from Chitinophaga pinensis

  • Jeroen S. Dickschat,
  • Jan Rinkel,
  • Patrick Rabe,
  • Arman Beyraghdar Kashkooli and
  • Harro J. Bouwmeester

Beilstein J. Org. Chem. 2017, 13, 1770–1780, doi:10.3762/bjoc.13.171

Graphical Abstract
  • synthases in plants are targeted to the mitochondria [27], we decided to attempt the expression of HdS with mitochondrial targeting (HdS-mit). A construct without targeting signal (HdS; resulting in cytoplasmic localisation) and an empty vector were used as controls. A p19 construct [28] was co-infiltrated
  • targeting to the mitochondria resulted in the production of the same diterpene alcohol. Although the mitochondria of N. benthamiana also produce FPP [32], again no germacrene D was detected. Taken together, these experiments demonstrate that the expression of one and the same terpene synthase in different
  • of GC–MS analyses of N. benthamiana leaf extracts. A) HdS-mit (HdS expressed with mitochondrial targeting signal) showing the production of 3 in planta, B) HdS (expression without targeting signal) and C) empty vector. Germacrene A (1) and its Cope rearrangement to β-elemene (2). Product obtained
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Published 23 Aug 2017

The chemistry and biology of mycolactones

  • Matthias Gehringer and
  • Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

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  • relies on the experience of local health professionals. Subsequent laboratory testing to confirm the clinical diagnosis might then be performed by 1) direct smear examination for acid-fast bacilli; 2) in vitro culture; 3) polymerase chain reaction (PCR), targeting the genomic region IS2404; and 4
  • accompanied by macroscopic or ultrastructural signs of nerve destruction and hypoesthesia. Subsequent experiments revealed that mycolactone exposure caused hyperpolarization of neurons derived from PC12 cells that was mediated by the TRAAK potassium channel. Finally, screening of a siRNA library targeting
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Published 11 Aug 2017

Synthesis of oligonucleotides on a soluble support

  • Harri Lönnberg

Beilstein J. Org. Chem. 2017, 13, 1368–1387, doi:10.3762/bjoc.13.134

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  • in the development of therapeutic oligonucleotides targeting either pre-mRNA [24][25], mature mRNA [26][27][28] or noncoding microRNA [29][30] have even increased this interest. It has been repeatedly argued that (i) the synthesis in solution could be carried out with a smaller excess of building
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Published 12 Jul 2017

BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

  • Ludmila Škorpilová,
  • Silvie Rimpelová,
  • Michal Jurášek,
  • Miloš Buděšínský,
  • Jana Lokajová,
  • Roman Effenberg,
  • Petr Slepička,
  • Tomáš Ruml,
  • Eva Kmoníčková,
  • Pavel B. Drašar and
  • Zdeněk Wimmer

Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128

Graphical Abstract
  • theranostic applications. Keywords: BODIPY conjugates; cancer targeting; drug delivery; liposomes; natural compounds; sesquiterpene lactone trilobolide; Introduction Targeted (smart) drug delivery is a method for specific delivering of an active compound preferentially to some cells or tissues in the human
  • body. This approach has become the key issue for surpassing the bottleneck of drug discovery. With the advent of new technologies and deeper understanding of the biological processes, the concept of specific targeting has become one of the most attractive directions in the field of biomedicine
  • . Specific drug targeting can be achieved by using, for example, antibodies, peptides, polyethylene glycol polymers, and last but not least, liposomes, which have been nowadays extensively investigated [1][2]. In general, liposomes are employed in order to enhance the therapeutic index of an applied drug by
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Published 04 Jul 2017

Aqueous semisynthesis of C-glycoside glycamines from agarose

  • Juliana C. Cunico Dallagnol,
  • Alexandre Orsato,
  • Diogo R. B. Ducatti,
  • Miguel D. Noseda,
  • Maria Eugênia R. Duarte and
  • Alan G. Gonçalves

Beilstein J. Org. Chem. 2017, 13, 1222–1229, doi:10.3762/bjoc.13.121

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  • recently envisaged that its substituted C-threofuranose ring could serve as an excellent scaffold to build muscarine analogues [11]. Cholinergic agents targeting muscarinic acetylcholine receptors (mAChRs) have historically served for diverse applications in medicine [12][13] and recently regained interest
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Published 23 Jun 2017
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