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1.
Chem Commun (Camb) ; 56(10): 1549-1552, 2020 Feb 04.
Artigo em Inglês | MEDLINE | ID: mdl-31930244

RESUMO

In accordance with the rapid increase in demand for selective and spatial chemical tagging, and accurate detection of proteins of interest, we develop a sensitive protein detection method, termed "Supra-blot" capitalizing on high-affinity host-guest interaction between cucurbit[7]uril (CB[7]) and adamantylammonium (AdA). The method can directly detect chemically tagged proteins without false-positive signals caused by endogenous biomolecules. Not only a single specific protein, but also spatially localized proteins in cells were labeled with AdA, and selectively detected by a host molecule-enzyme hybrid, CB[7]-conjugated horseradish peroxidase (CB[7]-HRP) generating amplified chemiluminescence signals. This study shows the great potential of Supra-blot for accurate and reliable detection of proteins of interest in cells.


Assuntos
Hidrocarbonetos Aromáticos com Pontes/química , Peroxidase do Rábano Silvestre/química , Imidazóis/química , Medições Luminescentes/métodos , Amantadina/química , Compostos de Amônio/química , Células HEK293 , Histonas/química , Histonas/metabolismo , Peroxidase do Rábano Silvestre/metabolismo , Humanos
2.
Chem Commun (Camb) ; 56(15): 2296-2299, 2020 Feb 20.
Artigo em Inglês | MEDLINE | ID: mdl-31989125

RESUMO

We developed an epigenetically active, cooperative DNA binding transcription factor platform assisted by cucurbit[7]uril (CB7) host-guest modules. This new type of molecule termed ePIP-HoGu not only mimics the operation of transcription factors as a pair but also recruits the epigenetic modifier to a particular DNA locus.


Assuntos
DNA/química , Epigênese Genética/genética , Fatores de Transcrição/química , Hidrocarbonetos Aromáticos com Pontes/química , DNA/genética , Imidazóis/química , Estrutura Molecular , Fatores de Transcrição/síntese química , Fatores de Transcrição/genética
3.
Chem Commun (Camb) ; 56(11): 1629-1632, 2020 Feb 06.
Artigo em Inglês | MEDLINE | ID: mdl-31939471

RESUMO

This article presents a new label-free fluorescence assay based on supramolecular self-assembly of cucurbit[7]uril and specific peptide Gly-Pro-Phe-Gly for monitoring DPP4 activity in clinical samples. It also displays a good potential application in high-throughput screening of DPP4 inhibitors.


Assuntos
Dipeptidil Peptidase 4/sangue , Ensaios Enzimáticos/métodos , Laranja Acridina/química , Animais , Hidrocarbonetos Aromáticos com Pontes/química , Dipeptidil Peptidase 4/química , Inibidores da Dipeptidil Peptidase IV/química , Feminino , Corantes Fluorescentes/química , Humanos , Imidazóis/química , Limite de Detecção , Masculino , Camundongos Endogâmicos C57BL , Oligopeptídeos/química , Espectrometria de Fluorescência/métodos
4.
Chemistry ; 26(1): 198-205, 2020 Jan 02.
Artigo em Inglês | MEDLINE | ID: mdl-31643112

RESUMO

A 2D supramolecular organic framework (SOF) based on synthetic macrocycles has been constructed in water by a self-assembly strategy. Two new organic monomers of this SOF, possessing viologen and azobenzene functional groups, form a stimuli-responsive host-guest system upon cooperatively binding with cucurbit[8]uril rings. The reversible formation and dissociation of 2D SOF can be realized by the isomerization of azobenzene under ultraviolet and visible light. The light-responsive property of the SOF is highly reversible and stable for up to four cycles. Moreover, azoreductase produced by Escherichia coli can reduce the N=N double bond of azobenzene entities, resulting in fluorescence recovery of the system. As an excellent and effective fluorescent probe, the SOF can detect azoreductase activity for real-time monitoring of the growth process of Escherichia coli. The dual-stimuli responsive 2D SOF is envisioned to drive the development of responsive devices with complex functions.


Assuntos
Substâncias Macromoleculares/química , NADH NADPH Oxirredutases/metabolismo , Compostos Azo/química , Hidrocarbonetos Aromáticos com Pontes/química , Escherichia coli/metabolismo , Imidazóis/química , Isomerismo , Luz , Substâncias Macromoleculares/metabolismo , NADH NADPH Oxirredutases/química , NADH NADPH Oxirredutases/genética , Proteínas Recombinantes/biossíntese , Proteínas Recombinantes/química , Espectrometria de Fluorescência
5.
Chem Commun (Camb) ; 56(3): 360-363, 2020 Jan 02.
Artigo em Inglês | MEDLINE | ID: mdl-31825399

RESUMO

A crystalline biohybrid with a 4 : 1 protein : cucurbituril mass ratio is presented. This result was achieved by engineering additional cucurbit[7]uril (Q7) binding sites into a ß-propeller protein. In contrast to the parent protein, Q7-controlled assembly of the engineered variant occurred in solution, as evidenced by NMR and SAXS measurements.


Assuntos
Proteínas de Bactérias/química , Hidrocarbonetos Aromáticos com Pontes/química , Imidazóis/química , Sequência de Aminoácidos , Proteínas de Bactérias/metabolismo , Sítios de Ligação , Hidrocarbonetos Aromáticos com Pontes/metabolismo , Imidazóis/metabolismo , Lectinas/química , Lectinas/genética , Lectinas/metabolismo , Ressonância Magnética Nuclear Biomolecular , Ralstonia solanacearum/metabolismo , Espalhamento a Baixo Ângulo , Difração de Raios X
6.
Food Microbiol ; 86: 103335, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-31703853

RESUMO

The presence of eight common structural enterocin genes, singly or in varying combinations, in the genome of 15 antagonistic Enterococcus spp. previously isolated from artisan Greek Graviera and Galotyri retail cheeses was tested and associated with the mode of enterocin (Ent+) antilisterial activity of each isolate in three liquid culture media. The isolates were assigned to nine distinct strain genotypes of E. faecium (4 strains), E. durans (2) and E. faecalis (3). All strains were non-hemolytic, except for a cyl-positive E. faecalis genotype isolated from Galotyri cheese, which was strongly listericidal. All other strains varied from being listeriostatic to weakly listericidal in MRS and M17 broth, whereas all failed to inhibit listerial growth in skim milk. Two E. faecium strains retained strong Ent+ activity following neutralization and filter-sterilization of their MRS or M17 co-culture supernatants, whereas, all others required contact or proximity of their viable cells with L. monocytogenes cells in order to display activity. Additional studies to evaluate safety and potential synergistic effects of each strain genotype with starter LAB species in real milk environments will reveal the most active and truly harmless Enterococcus genotypes to be applied as co-starter or bioprotective adjunct cultures in traditional Greek cheese technologies.


Assuntos
Queijo/microbiologia , Enterococcus/química , Listeria monocytogenes/efeitos dos fármacos , Leite/microbiologia , Animais , Hidrocarbonetos Aromáticos com Pontes/química , Hidrocarbonetos Aromáticos com Pontes/metabolismo , Hidrocarbonetos Aromáticos com Pontes/farmacologia , Bovinos , Meios de Cultura/química , Meios de Cultura/metabolismo , Enterococcus/genética , Enterococcus/isolamento & purificação , Enterococcus/metabolismo , Grécia , Listeria monocytogenes/crescimento & desenvolvimento
8.
Chem Commun (Camb) ; 55(92): 13820-13823, 2019 Nov 14.
Artigo em Inglês | MEDLINE | ID: mdl-31664274

RESUMO

A supramolecular nanocapsule was constructed by the ternary host-guest complexation of azobenzene (Azo) and methylviologen (MV) to cucurbit[8]uril (CB[8]) and the subsequent self-assembly. The supramolecular nanocapsule with both glutathione peroxidase (GPx) and superoxide dismutase (SOD) activities can mimic the intracellular enzymatic reactive oxygen species (ROS) defense system.


Assuntos
Antioxidantes/química , Hidrocarbonetos Aromáticos com Pontes/química , Imidazóis/química , Nanocápsulas/química , Células 3T3 , Animais , Compostos Azo/química , Materiais Biocompatíveis/química , Materiais Biocompatíveis/metabolismo , Sobrevivência Celular/efeitos dos fármacos , Glutationa Peroxidase/química , Glutationa Peroxidase/metabolismo , Camundongos , Microscopia Confocal , Nanocápsulas/toxicidade , Paraquat/química , Espécies Reativas de Oxigênio/química , Superóxido Dismutase/química , Superóxido Dismutase/metabolismo
9.
J Chem Theory Comput ; 15(11): 5829-5844, 2019 Nov 12.
Artigo em Inglês | MEDLINE | ID: mdl-31593627

RESUMO

A powerful computational strategy to determine the equilibrium association constant of two macromolecules with explicit-solvent molecular dynamics (MD) simulations is the "geometric route", which considers the reversible physical separation of the bound complex in solution. Nonetheless, multiple challenges remain to render this type of methodology reliable and computationally efficient in practice. In particular, in one, formulation of the geometric route relies on the potential of mean force (PMF) for physically separating the two binding partners restrained along a straight axis, which must be selected prior to the calculation. However, practical applications indicate that the calculation of the separation PMF along the predefined rectilinear pathway may be suboptimal and slowly convergent. Recognizing that a rectilinear straight separation pathway is generally not representative of how the protein complex physically separates in solution, we put forth a novel theoretical framework for binding free-energy calculations, leaning on the optimal curvilinear minimum free-energy path (MFEP) determined from the string method. The proposed formalism is validated by comparing the results obtained using both rectilinear and curvilinear pathways for a prototypical host-guest complex formed by cucurbit[7]uril (CB[7]) binding benzene, and for the barnase-barstar protein complex. On the basis of multi-microsecond MD calculations, we find that the calculations following the traditional rectilinear pathway and the string-based curvilinear pathway agree quantitatively, but convergence is faster with the latter.


Assuntos
Simulação de Dinâmica Molecular , Proteínas/química , Proteínas de Bactérias/química , Proteínas de Bactérias/metabolismo , Benzeno/química , Benzeno/metabolismo , Hidrocarbonetos Aromáticos com Pontes/química , Hidrocarbonetos Aromáticos com Pontes/metabolismo , Imidazóis/química , Imidazóis/metabolismo , Ligação Proteica , Proteínas/metabolismo , Ribonucleases/química , Ribonucleases/metabolismo , Termodinâmica
10.
Anal Bioanal Chem ; 411(27): 7293-7301, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31598741

RESUMO

A simple, sensitive, and naked-eye assay of metformin (MET), based on the host-guest molecular recognition of cucurbit[6]uril (CB[6])-modified silver nanoparticles, has been developed for the first time. The molecular recognition between CB[6] and MET is initially demonstrated and the related recognition mechanism is further discussed. CB[6]-modified AgNPs were first synthesized and then characterized by UV-vis spectroscopy, Fourier transform infrared spectroscopy, and transmission electron microscopy. The solution behavior of CB[6] in the presence of AgNO3 was also studied, and the correlative result revealed that AgNPs could combine with the carbonyl portals of CB[6]. On the basis of the molecular recognition of CB[6] and the surface plasmon resonance effect of AgNPs, CB[6]-modified AgNPs were used as visual probes to detect MET. In CB[6]-modified AgNP solution, the aggregation of CB[6]-modified AgNPs induced by MET triggered changes of color and the UV-vis absorption spectrum, which laid the foundation for the visual identification and spectrophotometric determination of MET. Under the optimized detection conditions, the UV-vis spectral assay had a good linear relationship in the range from 3 to 750 µM, and the limit of detection was 1 µM. According to the color changes, the minimum concentration recognized by the naked eye was about 75 µM. Furthermore, this assay has high selectivity for coexisting interferents and was also applied to MET detection in human urine samples. This strategy provides a novel and facile tool for highly selective and sensitive detection of MET. Graphical abstract.


Assuntos
Hidrocarbonetos Aromáticos com Pontes/química , Hipoglicemiantes/urina , Imidazóis/química , Nanopartículas Metálicas/química , Metformina/urina , Prata/química , Colorimetria , Humanos , Limite de Detecção , Nanopartículas Metálicas/ultraestrutura , Espectrofotometria Ultravioleta/métodos , Urinálise/métodos
11.
Chem Commun (Camb) ; 55(90): 13506-13509, 2019 Nov 07.
Artigo em Inglês | MEDLINE | ID: mdl-31626260
12.
Int J Mol Sci ; 20(17)2019 Aug 30.
Artigo em Inglês | MEDLINE | ID: mdl-31480231

RESUMO

Human cytochrome P450 3A4 (CYP3A4) is the most important drug-metabolizing enzyme. Some drugs and natural compounds can act as suicide (mechanism-based) inactivators of CYP3A4, leading to unanticipated drug-drug interactions, toxicity and therapeutic failures. Despite significant clinical and toxicological implications, the mechanism-based inactivation remains incompletely understood. This study provides the first direct insights into the interaction of CYP3A4 with three suicide substrates: mibefradil, an antihypertensive drug quickly withdrawn from the market; a semi-synthetic antibiotic azamulin; and a natural furanocoumarin, 6',7'-dihydroxybergamottin. Novel structural findings help better understand the suicide substrate binding and inhibitory mechanism, and can be used to improve the predictability of the binding ability, metabolic sites and inhibitory/inactivation potential of newly developed drugs and other chemicals relevant to public health.


Assuntos
Hidrocarbonetos Aromáticos com Pontes/química , Hidrocarbonetos Aromáticos com Pontes/metabolismo , Citocromo P-450 CYP3A/química , Citocromo P-450 CYP3A/metabolismo , Furocumarinas/química , Furocumarinas/metabolismo , Mibefradil/química , Mibefradil/metabolismo , Triazóis/química , Triazóis/metabolismo , Cristalografia por Raios X , Humanos , Modelos Moleculares , Especificidade por Substrato
13.
Chem Commun (Camb) ; 55(72): 10654-10664, 2019 Sep 16.
Artigo em Inglês | MEDLINE | ID: mdl-31418758

RESUMO

Some host-guest complexes of cucurbit[n]uril (CB[n]) host molecules act as supramolecular amphiphiles (SAs), which hierarchically self-assemble into various nanomaterials such as vesicles, micelles, nanorods, and nanosheets in water. The structures and functions of the nanomaterials can be controlled by supramolecular engineering of the host-guest complexes. In addition, functionalization at the periphery of CB[6] and CB[7] generates CB[n]-based molecular amphiphiles (MAs) that can also self-assemble into vesicles or micelle-like nanoparticles in water. Taking advantage of the molecular cavities of CBs and their strong guest recognition properties, the surface of the self-assembled nanomaterials can be easily decorated with various functional tags in a non-covalent manner. In this feature article, the two types (SAs and MAs) of CB-based amphiphiles, their self-assemblies and their applications for nanotherapeutics and theranostics are presented with future perspectives.


Assuntos
Antibióticos Antineoplásicos/farmacologia , Hidrocarbonetos Aromáticos com Pontes/farmacologia , Doxorrubicina/farmacologia , Nanoestruturas/química , Tensoativos/farmacologia , Antibióticos Antineoplásicos/química , Hidrocarbonetos Aromáticos com Pontes/química , Proliferação de Células/efeitos dos fármacos , Doxorrubicina/química , Células HeLa , Humanos , Células KB , Tensoativos/química
14.
Chemistry ; 25(57): 13088-13093, 2019 Oct 11.
Artigo em Inglês | MEDLINE | ID: mdl-31441544

RESUMO

A convenient supramolecular strategy for constructing a ratiometric fluorescent chemosensing ensemble, consisting of a macrocyclic host (cucurbit[8]uril CB[8]), and a pyrene-tagged amphiphilic peptide beacon (AP 1), is reported. AP 1 unfolds upon encapsulation of the pyrene termini into the hydrophobic CB[8] cavity. This changes pyrene excimer to monomer emission. Substrates with higher affinity for the CB[8] cavity can displace AP 1 from the ensemble. The released AP 1 folds again to form a pyrene excimer, which allows for the ratiometric fluorescence monitoring of the substrate. In this report, the ensemble capacity for ratiometric fluorescence monitoring of biological substrates, such as amino acid derivatives, specific peptides, and proteins, in aqueous media is demonstrated.


Assuntos
Hidrocarbonetos Aromáticos com Pontes/química , Imidazóis/química , Substâncias Macromoleculares/química , Oligopeptídeos/química , Peptídeos/análise , Pirenos/química , Hidrocarbonetos Aromáticos com Pontes/metabolismo , Fluorescência , Imidazóis/metabolismo , Oligopeptídeos/metabolismo , Peptídeos/química , Água/química
15.
Molecules ; 24(12)2019 Jun 21.
Artigo em Inglês | MEDLINE | ID: mdl-31234313

RESUMO

Oligonucleotides are key compounds widely used for research, diagnostics, and therapeutics. The rapid increase in oligonucleotide-based applications, together with the progress in nucleic acids research, has led to the design of nucleotide analogs that, when part of these oligomers, enhance their efficiency, bioavailability, or stability. One of the most useful nucleotide analogs is the first-generation bridged nucleic acids (BNA), also known as locked nucleic acids (LNA), which were used in combination with ribonucleotides, deoxyribonucleotides, or other analogs to construct oligomers with diverse applications. However, there is still room to improve their efficiency, bioavailability, stability, and, importantly, toxicity. A second-generation BNA, BNANC (2'-O,4'-aminoethylene bridged nucleic acid), has been recently made available. Oligomers containing these analogs not only showed less toxicity when compared to LNA-containing compounds but, in some cases, also exhibited higher specificity. Although there are still few applications where BNANC-containing compounds have been researched, the promising results warrant more effort in incorporating these analogs for other applications. Furthermore, newer BNA compounds will be introduced in the near future, offering great hope to oligonucleotide-based fields of research and applications.


Assuntos
Hidrocarbonetos Aromáticos com Pontes/química , Oligonucleotídeos/química , Etilenos/química
16.
ACS Appl Mater Interfaces ; 11(26): 22925-22931, 2019 Jul 03.
Artigo em Inglês | MEDLINE | ID: mdl-31252492

RESUMO

Covalently self-assembled polymer nanocapsules (NCs) based on cucurbit[6]uril have been previously prepared and their applications in payload delivery and bioimaging have been demonstrated, showing significant potentials. However, the preparation of these NCs often requires laborious and tedious multistep reactions, including a low-yield conversion of perhydroxycucurbit[6]uril to perallyloxycucurbit[6]uril, subsequent photopolymerization of perallyloxycucurbit[6]uril with dithiol linkers, and two additional steps of treatment to remove disulfide loops and create cationic sulfoniums. Herein, we report a novel, facile approach leading to cucurbit[6]uril-based polymer NCs via direct alkylation of perhydroxycucurbit[6]uril with a ditopic linker, thereby saving significant time and efforts, which may lead to significant expansion in investigations of these unique materials in various applications, particularly biomedical sciences. As a proof of concept, we have further demonstrated that a photosensitive therapeutic payload, such as chlorin e6, may get encapsulated inside the NCs for improved, targeted photodynamic therapy against cancer cells.


Assuntos
Hidrocarbonetos Aromáticos com Pontes/síntese química , Imidazóis/síntese química , Nanocápsulas/química , Neoplasias/terapia , Fotoquimioterapia , Alquilação/efeitos dos fármacos , Hidrocarbonetos Aromáticos com Pontes/química , Hidrocarbonetos Aromáticos com Pontes/farmacologia , Humanos , Imidazóis/química , Imidazóis/farmacologia , Nanocápsulas/uso terapêutico , Polímeros/química , Polímeros/farmacologia , Porfirinas/química
17.
Org Biomol Chem ; 17(25): 6215-6220, 2019 06 26.
Artigo em Inglês | MEDLINE | ID: mdl-31179469

RESUMO

Here we report the endocytosis and excretion pathways of two different dye-conjugated cucurbit[7]urils, (cyanine 3-conjugated CB[7] and rhodamine X-conjugated CB[7]), which have great potential as molecular probes for live cell imaging. The dye-CB[7]s are translocated into live cells (human breast carcinoma cells, MCF-7) via multiple pathways, predominantly by clathrin-mediated endocytosis, and excreted from cells via lysosome-associated exocytosis. Interestingly, the CB[7] moiety has a substantial influence on the uptake and excretion pathways. These findings may widen the applications of the dyes conjugated to CB[7] and assist in the design of new molecular probes for live cell imaging.


Assuntos
Hidrocarbonetos Aromáticos com Pontes/metabolismo , Carbocianinas/metabolismo , Endocitose/fisiologia , Exocitose/fisiologia , Corantes Fluorescentes/metabolismo , Imidazóis/metabolismo , Rodaminas/metabolismo , Hidrocarbonetos Aromáticos com Pontes/química , Carbocianinas/química , Fluorescência , Corantes Fluorescentes/química , Humanos , Imidazóis/química , Lisossomos/fisiologia , Células MCF-7 , Rodaminas/química
18.
Molecules ; 24(11)2019 Jun 08.
Artigo em Inglês | MEDLINE | ID: mdl-31181726

RESUMO

A series of novel 7,9-O-linked macrocyclic taxoids together with modification at the C2 position were synthesized, and their cytotoxicities against drug-sensitive and P-glycoprotein and ßIII-tubulin overexpressed drug-resistant cancer cell lines were evaluated. It is demonstrated that C-seco taxoids conformationally constrained via carbonate containing-linked macrocyclization display increased cytotoxicity on drug-resistant tumors overexpressing both ßIII and P-gp, among which compound 22b, bearing a 2-m-methoxybenzoyl group together with a five-atom linker, was identified as the most potent. Molecular modeling suggested the improved cytotoxicity of 22b results from enhanced favorable interactions with the T7 loop region of ßIII.


Assuntos
Compostos Macrocíclicos/síntese química , Compostos Macrocíclicos/farmacologia , Taxoides/síntese química , Taxoides/farmacologia , Hidrocarbonetos Aromáticos com Pontes/síntese química , Hidrocarbonetos Aromáticos com Pontes/química , Hidrocarbonetos Aromáticos com Pontes/farmacologia , Morte Celular/efeitos dos fármacos , Docetaxel/síntese química , Docetaxel/química , Docetaxel/farmacologia , Células HeLa , Humanos , Compostos Macrocíclicos/química , Simulação de Acoplamento Molecular , Paclitaxel/síntese química , Paclitaxel/química , Paclitaxel/farmacologia , Homologia Estrutural de Proteína , Taxoides/química , Tubulina (Proteína)/química
19.
Chemistry ; 25(42): 9827-9833, 2019 Jul 25.
Artigo em Inglês | MEDLINE | ID: mdl-31141233

RESUMO

Oncogenic Ras mutations occur in more than 30 % of human cancers. K-Ras4B is the most frequently mutated isoform of Ras proteins. Development of effective K-Ras4B inhibitors has been challenging, hence new approaches to inhibit this oncogenic protein are urgently required. The polybasic domain of K-Ras4B with its stretch of lysine residues is essential for its plasma membrane targeting and localization. Employing CD and fluorescence spectroscopy, confocal fluorescence, and atomic force microscopy we show that the molecular tweezer CLR01 is able to efficiently bind to the lysine stretch in the polybasic domain of K-Ras4B, resulting in dissociation of the K-Ras4B protein from the lipid membrane and disintegration of K-Ras4B nanoclusters in the lipid bilayer. These results suggest that targeting of the polybasic domain of K-Ras4B by properly designed tweezers might represent an effective strategy for inactivation of K-Ras4B signaling.


Assuntos
Hidrocarbonetos Aromáticos com Pontes/química , Membrana Celular/química , Bicamadas Lipídicas/química , Lipídeos de Membrana/química , Organofosfatos/química , Proteínas Proto-Oncogênicas p21(ras)/química , Simulação por Computador , Humanos , Mutação , Nanoestruturas/química , Conformação Proteica , Termodinâmica
20.
Chem Biodivers ; 16(7): e1900175, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31095891

RESUMO

Several species from the Apocynaceae family, such as Tabernanthe iboga, Voacanga africana, and many Tabernaemontana species, produce ibogan type alkaloids, some of which present antiaddictive properties. In this study, we used gas chromatography/mass spectrometry (GC/MS) to examine the efficiency of methanol, acetone, ethyl acetate, dichloromethane, chloroform, and hydrochloric acid in extracting the antiaddictive compounds coronaridine, ibogamine, voacangine, and ibogaine (altogether the CIVI-complex) from the root barks of Tabernaemontana alba and Tabernaemontana arborea. These Mexican species have recently shown great potential as alternative natural sources of the aforementioned substances. Methanol proved to be the most suitable solvent. Furthermore, the crude methanolic extracts could be engaged in a one-step demethoxycarbonylation process that converted coronaridine and voacangine directly into its non-carboxylic counterparts ibogamine and ibogaine, respectively, without the intermediacy of their carboxylic acids. The established protocol straightforwardly simplifies the alkaloid mixture from four to two majority compounds. In summary, our findings facilitate and improve both the qualitative and quantitative analysis of CIVI-complex-containing plant material, as well as outlining a viable method for the bulk production of these scientifically and pharmaceutically important substances from Mexican Tabernaemontana species.


Assuntos
Hidrocarbonetos Aromáticos com Pontes/isolamento & purificação , Ibogaína/análogos & derivados , Ibogaína/isolamento & purificação , Tabernaemontana/química , Hidrocarbonetos Aromáticos com Pontes/química , Ibogaína/química , México , Conformação Molecular , Casca de Planta/química , Raízes de Plantas/química , Especificidade da Espécie
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