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1.
J Cell Mol Med ; 23(9): 6085-6097, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31270949

RESUMO

The surged systemic vascular inflammation after acute myocardial infarction (AMI) aggravates the atherosclerotic endothelial injury. To explore roles of miR-499 released from cardiomyocytes during AMI in endothelial injury. Using qPCR and ELISA, we discovered that patients with AMI had significantly increased plasma miR-499, which was directly correlated with serum thrombomodulin, a marker for endothelial injury. Plasma of AMI patients, when incubated with human umbilical vein endothelial cells (HUVECs), significantly increased the expression of endothelial injury markers, which could be abrogated by antagomiR-499. In vitro, neonatal rat cardiomyocytes subjected to hypoxia/reoxygenation (HX/R) released miR-499 that could be internalized into rat pulmonary microvascular endothelial cells (RPMECs), worsening the high glucose-induced injury. In silico analysis demonstrated that CHRNA7 encoding α7-nAchR is a target of miR-499, which was validated in cell lines expressing endogenous α7-nAchR. In high glucose-induced RPMECs injury model, miR-499 aggravated, whereas forced CHRNA7 expression ameliorated the injury. Moreover, the perfusate from Langendorff perfused rat heart subjected to HX/R contained higher level of miR-499 that significantly impaired the Bradykinin-mediated endothelium-dependent relaxation in both conduit and resistance arteries, which could be partially abrogated by antagomiR-499. Finally, the correlation between plasma miR-499 and endothelial injury was further confirmed in another cohort of AMI patients. We conclude that miR-499 released from injured cardiomyocytes contributes to the endothelial injury by targeting α7-nAchR. This study implies that miR-499 may serve as a potential target for the treatment of the surged vascular inflammation post-AMI.

2.
Cell Signal ; 62: 109327, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31152845

RESUMO

Esophageal cancer related gene-4 (ECRG4) inhibits the malignant phenotype of oral squamous cell carcinoma. However, the molecular mechanisms remain to be explored. Using the tongue carcinoma cell line, TCA8113 as a cell model, we showed that forced expression of ECRG4 down-regulated the expression of the BC200 long non-coding RNA (lncRNA) and matrix metalloproteinases (MMP-9 and MMP-13). Restoration of BC200 lncRNA rescued ECRG4-mediated down-regulation of MMP-9 and -13. Furthermore, over-expression of Ecrg4 inhibited cell proliferation and migration, which was abolished by forced expression of BC200 lncRNA in TCA8113 cells. Our results indicate that ECRG4 inhibits the malignant phenotype of TCA8113 cells most likely through suppression of BC200 lncRNA/MMPs signaling pathway, rationalizing that BC200 lncRNA may be a potential target for oral squamous cell carcinoma (OSCC) therapy.

3.
Biomed Pharmacother ; 113: 108594, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-30849639

RESUMO

The healing of acute wounds is vital to humans and is a well-orchestrated process that involves systemic and local factors. However, there is a lack of effective and safe clinical therapies. The collagen triple helix repeat containing 1 (CTHRC1) protein is a type of exocrine protein that has been recently reported to contribute to tissue repair. Our aim is to validate the promoting effects of CTHRC1 on the healing of acute wounds and to elucidate the underlying molecular mechanism. Therefore, we first established acute wound healing mouse models and confirmed that CTHRC1 accelerates the healing process of acute wounds. Then, we characterized wound macrophages using a polyvinylalcohol (PVA) sponge model and used Western blotting to investigate the molecular mechanism. We found that CTHRC1 increased the M2 macrophage population and the TGF-ß expression level as a result of the activation of the TGF-ß and Notch pathways, which eventually contributed to the promotion of wound healing. Inhibition of the Notch pathway showed attenuated M2 macrophage recruitment, and it decreased the TGF-ß expression level. These results substantiate our hypothesis that CTHRC1 promotes wound healing by recruiting M2 macrophages and regulating the TGF-ß and Notch pathways.


Assuntos
Proteínas da Matriz Extracelular/farmacologia , Macrófagos/efeitos dos fármacos , Receptores Notch/metabolismo , Pele/lesões , Fator de Crescimento Transformador beta/metabolismo , Cicatrização/efeitos dos fármacos , Ferimentos Perfurantes/tratamento farmacológico , Animais , Linhagem Celular , Modelos Animais de Doenças , Humanos , Macrófagos/imunologia , Masculino , Camundongos , Camundongos Endogâmicos C57BL , Proteínas Recombinantes/farmacologia , Transdução de Sinais , Pele/imunologia , Pele/metabolismo , Cicatrização/imunologia , Ferimentos Perfurantes/imunologia , Ferimentos Perfurantes/metabolismo
4.
Wound Repair Regen ; 24(6): 1004-1014, 2016 11.
Artigo em Inglês | MEDLINE | ID: mdl-27663454

RESUMO

Mice engrafted with human CD34+ hematopoietic stem and progenitor cells (CD34+ -HSPCs) have been used to study human infection, diabetes, sepsis, and burn, suggesting that they could be highly amenable to characterizing the human inflammatory response to injury. To this end, human leukocytes infiltrating subcutaneous implants of polyvinyl alcohol (PVA) sponges were analyzed in immunodeficient NSG mice reconstituted with CD34+ -HSPCs. It was reported that human CD45+ (hCD45+ ) leukocytes were present in PVA sponges 3 and 7 days postimplantation and could be localized within the sponges by immunohistochemistry. The different CD45+ subtypes were characterized by flow cytometry and the profile of human cytokines they secreted into PVA wound fluid was assessed using a human-specific multiplex bead analyses of human IL-12p70, TNFα, IL-10, IL-6, IL1ß, and IL-8. This enabled tracking the functional contributions of HLA-DR+ , CD33+ , CD19+ , CD62L+ , CD11b+ , or CX3CR1+ hCD45+ infiltrating inflammatory leukocytes. PCR of cDNA prepared from these cells enabled the assessment and differentiation of human, mouse, and uniquely human genes. These findings support the hypothesis that mice engrafted with CD34+ -HSPCs can be deployed as precision avatars to study the human inflammatory response to injury.


Assuntos
Transplante de Células-Tronco Hematopoéticas , Inflamação/imunologia , Inflamação/patologia , Células Supressoras Mieloides/imunologia , Células Supressoras Mieloides/patologia , Animais , Células Cultivadas , Modelos Animais de Doenças , Citometria de Fluxo , Humanos , Imuno-Histoquímica , Interleucina-10/metabolismo , Interleucina-6/metabolismo , Interleucina-8/metabolismo , Camundongos , Camundongos Endogâmicos NOD , Células Supressoras Mieloides/metabolismo , Transdução de Sinais , Cicatrização/imunologia , Ferimentos e Lesões/imunologia , Ferimentos e Lesões/metabolismo , Ferimentos e Lesões/patologia
5.
Chem Commun (Camb) ; 51(85): 15558-61, 2015 Nov 04.
Artigo em Inglês | MEDLINE | ID: mdl-26352340

RESUMO

A copper and iodine-mediated C-H oxidative sulfenylation of olefins with diaryl disulfides has been developed for the stereospecific synthesis of vinyl thioether. With the combination of Cu(OTf)2 and I2, a variety of terminal alkenes underwent oxidative coupling reaction with various diaryl disulfides successfully to afford the corresponding E-vinyl sulfides in moderate to good yields.


Assuntos
Alcenos/química , Cobre/química , Sulfetos/química , Sulfetos/síntese química , Iodo/química , Estrutura Molecular , Oxirredução , Estereoisomerismo
6.
Chem Commun (Camb) ; 51(19): 4097-100, 2015 Mar 07.
Artigo em Inglês | MEDLINE | ID: mdl-25666080

RESUMO

A new palladium-catalyzed oxidative carbamoylation reaction of isoquinoline N-oxides with formylamides for the synthesis of isoquinoline-1-carboxamides is established. The method represents the first example of the carbamoylation of isoquinoline N-oxides with formylamides to furnish arylamides using the dual C-H oxidation strategy.

7.
Mol Med Rep ; 11(4): 2471-6, 2015 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-25524174

RESUMO

Hypertrophic scarring (HS) is a type of fibrosis that occurs in the skin, and is characterized by fibroblast activation and excessive collagen production. However, at present, therapeutic strategies for this condition are ineffective. Previous studies have identified that the mutual regulation of chronic inflammation, mechanical force and fibroblast activation leads to the formation of HS. Induced pluripotent stem cells (iPSCs) are novel bioengineered embryonic­like stem cells, initially created from mouse adult fibroblasts. The current study demonstrated that iPSC­conditioned medium (iPSC­CM) may significantly suppress hypertrophic scar fibroblast activation. It was observed that in the presence of iPSC­CM, the level of collagen I was markedly reduced and α­smooth muscle actin, a marker for myofibroblasts (activated fibroblasts that mediate mechanical force­induced HS formation), exhibited a significantly lower level of expression in human dermal fibroblasts (HDFs) activated with transforming growth factor­ß1. Additionally, iPSC­CM attenuated the local inflammatory cell response by blocking the adhesion of human acute monocytic leukemia cell monocytes and fibroblasts in vitro. In addition, the contractile ability of HDFs may be reduced by iPSC­CM. These observations suggest that iPSC­CM may protect against processes leading to hypertrophic scarring by attenuating fibroblast activation, blocking inflammatory cell recruitment and adhesion and reducing the contractile ability of fibroblasts.


Assuntos
Meios de Cultivo Condicionados/farmacologia , Fibroblastos/efeitos dos fármacos , Fibroblastos/metabolismo , Células-Tronco Pluripotentes Induzidas/metabolismo , Animais , Adesão Celular/efeitos dos fármacos , Técnicas de Cultura de Células , Cicatriz Hipertrófica , Meios de Cultivo Condicionados/toxicidade , Camundongos
8.
Mol Med Rep ; 11(1): 182-8, 2015 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-25333210

RESUMO

Human adipose tissue stem cells (ATSCs) can differentiate into various types of cell in response to lineage-specific induction factors. Reprogramming cells using nuclear and cytoplasmic extracts derived from another type of somatic cell is an effective method of producing specific types of differentiated cell. In the present study, the ability of reprogrammed ATSCs to acquire epidermal keratinocyte properties following transient exposure to epidermal keratinocyte extracts was demonstrated. Reversibly permeabilized ATSCs were incubated for 1 h in nuclear and cytoplasmic extracts from epidermal keratinocytes, resealed with CaCl2 and cultured. ATSC reprogramming is demonstrated by nuclear uptake of epidermal keratinocyte extracts. After one week of exposure to extracts, ATSCs underwent changes in cell morphology, cell-specific genes were activated, and epidermal keratinocyte markers including K19 and K1/K10 (markers of stem cells and terminally differentiated keratinocytes, respectively) were expressed. This study indicates that the reprogramming of ATSCs using nuclear and cytoplasmic extracts from epidermal keratinocytes is a viable option for the production of specific types of cell.


Assuntos
Tecido Adiposo/citologia , Reprogramação Celular , Células Epidérmicas , Queratinócitos/metabolismo , Células-Tronco/citologia , Células-Tronco/metabolismo , Biomarcadores/metabolismo , Células Cultivadas , Expressão Gênica , Humanos , RNA Mensageiro/genética
9.
Chem Commun (Camb) ; 50(94): 14775-7, 2014 Dec 07.
Artigo em Inglês | MEDLINE | ID: mdl-25317723

RESUMO

A novel and convenient protocol for the formation of amides via palladium-catalyzed N-dealkylative carbonylation of alkyl tertiary amines has been developed. In the presence of PdCl2(PhCN)2, CuO, PhCN and CO, a range of substituents on both aryl iodides and alkyl tertiary amines were compatible with the reaction to afford a series of N,N-disubstituted amides in moderate to excellent yields.


Assuntos
Amidas/química , Aminas/química , Cetonas/química , Nitrogênio/química , Paládio/química , Alquilação , Catálise
10.
Int J Mol Sci ; 15(10): 18407-21, 2014 Oct 13.
Artigo em Inglês | MEDLINE | ID: mdl-25314301

RESUMO

Radiation therapy is the most widely used and effective treatment for orbital tumors, but it causes dry eye due to lacrimal gland damage. Induced pluripotent stem cell-derived conditioned medium (iPSC-CM) has been shown to rescue different types of tissue damage. The present study investigated the mechanism of the potential radioprotective effect of IPS cell-derived conditioned medium (iPSC-CM) on gamma-irradiation-induced lacrimal gland injury (RILI) in experimental mice. In this study, we found that iPSC-CM ameliorated RILI. iPSC-CM markedly decreased radiotherapy induced inflammatory processes, predominantly through suppressing p38/JNK signaling. Further signaling pathway analyses indicated that iPSC-CM could suppress Akt (Protein Kinase B, PKB) phosphorylation. High levels of midkine (MDK) were also found in iPSC-CM and could be involved in lacrimal gland regeneration by promoting cell migration and proliferation. Thus, our study indicates that inhibiting the p38/JNK pathway or increasing the MDK level might be a therapeutic target for radiation-induced lacrimal gland injury.


Assuntos
Meios de Cultivo Condicionados/farmacologia , Células-Tronco Pluripotentes Induzidas/metabolismo , Aparelho Lacrimal/efeitos dos fármacos , Aparelho Lacrimal/efeitos da radiação , Lesões Experimentais por Radiação/tratamento farmacológico , Protetores contra Radiação/farmacologia , Animais , Meios de Cultivo Condicionados/isolamento & purificação , Citocinas/isolamento & purificação , Citocinas/farmacologia , Feminino , Proteínas Quinases JNK Ativadas por Mitógeno/antagonistas & inibidores , Proteínas Quinases JNK Ativadas por Mitógeno/metabolismo , Aparelho Lacrimal/metabolismo , Aparelho Lacrimal/patologia , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Camundongos , Camundongos Endogâmicos C57BL , Midkina , Fatores de Crescimento Neural/isolamento & purificação , Fatores de Crescimento Neural/farmacologia , Lesões Experimentais por Radiação/metabolismo , Lesões Experimentais por Radiação/patologia , Protetores contra Radiação/isolamento & purificação , Radioterapia/efeitos adversos , Radioterapia/métodos , Proteínas Quinases p38 Ativadas por Mitógeno/antagonistas & inibidores , Proteínas Quinases p38 Ativadas por Mitógeno/metabolismo
11.
Chem Commun (Camb) ; 50(93): 14554-7, 2014 Dec 04.
Artigo em Inglês | MEDLINE | ID: mdl-25308914

RESUMO

A novel one-pot strategy for the synthesis of 3-trifluoromethylquinoxalines from N-aryl enamines and nitromethane was developed. The tandem reaction is achieved through nitrosation of alkenes, tautomerization and cyclization, which can be applicable to a wide range of enamines with excellent functional group tolerance and afford quinoxalines in moderate to good yields.


Assuntos
Aminas/química , Metano/análogos & derivados , Nitroparafinas/química , Quinoxalinas/síntese química , Ciclização , Metano/química , Estrutura Molecular , Nitrosação , Oxirredução , Quinoxalinas/química
12.
Biotechnol Lett ; 36(9): 1909-16, 2014 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-24930094

RESUMO

We have explored the feasibility of using adipose-derived stem cells (ADSCs) and polyglycolic acid (PGA) for constructing muscular tubes of urethra in a bioreactor. With the induction of by 5-azacytidine, ADSCs were found to acquire a myoblast phenotype. Here we seeded ADSCs in a PGA mesh to construct the cell-PGA complex that was cultured statically for 1 week. Afterwards, the cell-PGA complex was subjected to extension stimulation in a bioreactor for 5 weeks. A muscular tube of urethra was formed after 6 weeks. Histological examination showed differentiated ADSCs and collagenous fibers had orientated well. This study demonstrates that tissue engineering of urethra tissues in vitro by using a bioreactor leads to tissue maturation and the differentiation of ADSCs. This novel technique could provide an effective approach for urethra tissue engineering.


Assuntos
Diferenciação Celular , Mioblastos/fisiologia , Ácido Poliglicólico/metabolismo , Células-Tronco/fisiologia , Engenharia Tecidual/métodos , Uretra/fisiologia , Reatores Biológicos
14.
Biomaterials ; 35(1): 105-12, 2014 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-24140043

RESUMO

Urethral defects are common and frequent disorders and are difficult to treat. Simple natural or synthetic materials do not provide a satisfactory curative solution for long urethral defects, and urethroplasty with large areas of autologous tissues is limited and might interfere with wound healing. In this study, adipose-derived stem cells were used. These cells can be derived from a wide range of sources, have extensive expansion capability, and were combined with oral mucosal epithelial cells to solve the problem of finding seeding cell sources for producing the tissue-engineered urethras. We also used the synthetic biodegradable polymer poly-glycolic acid (PGA) as a scaffold material to overcome issues such as potential pathogen infections derived from natural materials (such as de-vascular stents or animal-derived collagen) and differing diameters. Furthermore, we used a bioreactor to construct a tissue-engineered epithelial-muscular lumen with a double-layer structure (the epithelial lining and the muscle layer). Through these steps, we used an epithelial-muscular lumen built in vitro to repair defects in a canine urethral defect model (1 cm). Canine urethral reconstruction was successfully achieved based on image analysis and histological techniques at different time points. This study provides a basis for the clinical application of tissue engineering of an epithelial-muscular lumen.


Assuntos
Músculo Liso/citologia , Engenharia Tecidual , Uretra/citologia , Tecido Adiposo/citologia , Animais , Diferenciação Celular , Cães , Células-Tronco/citologia
15.
PLoS One ; 8(6): e67124, 2013.
Artigo em Inglês | MEDLINE | ID: mdl-23840601

RESUMO

Lumican is a dermatan sulfate proteoglycan highly expressed in connective tissue and has the ability to regulate collagen fibril assembly. Previous studies have shown that lumican is involved in wound healing, but the precise effects of lumican on reepithelialization and wound contraction, the two pivotal aspects of skin wound healing, have not been investigated. Here we explored the roles of lumican in fibroblast contractility, a main aspect of skin wound healing, by adopting mice skin wound healing model and the corresponding in vitro cellular experiments. Our results showed that lumican can promote skin wound healing by facilitating wound fibroblast activation and contraction but not by promoting keratinocyte proliferation and migration. Silencing of integrin α2 completely abolished the pro-contractility of lumican, indicating lumican enhances fibroblast contractility via integrin α2. Our study for the first time demonstrated that lumican can affect fibroblast's mechanical property, which is pivotal for many important pathological processes, such as wound healing, fibrosis, and tumor development, suggesting that lumican might have a potential to be used to modulate these processes.


Assuntos
Fibroblastos/citologia , Fibroblastos/efeitos dos fármacos , Integrina alfa2beta1/metabolismo , Lumicana/farmacologia , Cicatrização/efeitos dos fármacos , Animais , Movimento Celular/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Fibroblastos/metabolismo , Inativação Gênica , Células HEK293 , Humanos , Integrina alfa2beta1/deficiência , Integrina alfa2beta1/genética , Masculino , Camundongos , Camundongos Endogâmicos BALB C , Proteínas Recombinantes/farmacologia , Pele/citologia
16.
Mol Med Rep ; 8(1): 201-4, 2013 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-23652299

RESUMO

The aim of this study was to present our experience of patients with penile strangulation. The clinical data of 6 patients (mean age, 36 years; range, 18-72 years) with penile strangulation caused by a metal hoop are provided, where the duration of strangulation was between 3 h and 1 month. Among these patients, the case of a 22-year-old patient with a steel hoop entrapment on his penis for 5 days is described; due to serious injury of the skin at the root of penis, an intermediate split­thickness thigh skin graft was used to repair the skin loss. A review of the literature is also provided in this study, and current treatment options and outcomes are evaluated. In all the cases described, the metal hoops were successfully removed, without gangrene of the penis. These patients were discharged 2-27 days later with a satisfactory outcome. Penile strangulation is an unusual clinical condition and the consequences may be severe. The choice of method for removal depends on the type and size of metal hoop, incarceration time, trauma grade and availability of equipment. Early treatment is essential to avoid potential complications, including ischemic necrosis and autoamputation.


Assuntos
Doenças do Pênis/etiologia , Doenças do Pênis/cirurgia , Pênis/lesões , Pênis/cirurgia , Adolescente , Adulto , Idoso , Humanos , Masculino , Pessoa de Meia-Idade , Doenças do Pênis/patologia , Pênis/patologia , Resultado do Tratamento , Adulto Jovem
17.
J Org Chem ; 78(12): 6025-30, 2013 Jun 21.
Artigo em Inglês | MEDLINE | ID: mdl-23710680

RESUMO

A palladium-catalyzed tandem Suzuki/C-H arylation reaction of N-aryltrifluoroacetimidoyl chlorides with arylboronic acids has been developed. A variety of 6-(trifluoromethyl)phenanthridines were prepared in moderate to excellent yields from N-(2-bromophenyl)trifluoroacetimidoyl chlorides which can be conveniently prepared from 2-bromoaniline derivatives.


Assuntos
Paládio/química , Fenantridinas/síntese química , Compostos de Anilina/química , Ácidos Borônicos/química , Catálise , Estrutura Molecular
18.
Mol Med Rep ; 7(3): 785-90, 2013 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-23338822

RESUMO

Hypertrophic scars are characterized by the abnormal proliferation of fibroblasts and an overproduction of collagen. The Sp1 transcription factor is involved in the stimulation of collagen synthesis. A decoy oligonucleotide (ODN) targeting Sp1 was designed and transfected into hypertrophic scar fibroblasts (HSFs) cells using cationic liposomes. The transfection efficiency was determined by flow cytometry and was observed to be 85±7% (n=5). Specific binding of the Sp1 decoy ODN was monitored with an electrophoretic mobility shift assay (EMSA). Following transfection with the decoy ODN to Sp1, cell viability and cell proliferation, which were examined by the cell counting kit WST­8, were decreased by 80% compared with untreated cells. Transforming growth factor­ß (TGF­ß) mRNA and collagen mRNA expression were also reduced by 48% in the transfection decoy ODN group. The cell viability of HSFs after 48 h of transfection with 25, 50, 100 and 150 nM Sp1 decoy ODN was 0.9331±0.0203, 0.7479±0.0868, 0.577±0.0347 and 0.4703±0.0147, respectively. The 100 nM dose of the Sp1 decoy ODN inhibited the expression of types I and III collagen by 32 and 28%, respectively (both P<0.01). TGF­ß mRNA expression was also effectively suppressed by the 100 nM Sp1 decoy ODN (P<0.01). The Sp1 decoy ODN inhibited cell proliferation and the expression of types I and III collagen. Therefore, Sp1 decoy ODNs may be a promising tool for developing and testing novel therapeutic applications for treating hypertrophic scars.


Assuntos
Cicatriz Hipertrófica/metabolismo , Colágeno Tipo III/genética , Colágeno Tipo I/genética , Fibroblastos/metabolismo , Oligonucleotídeos Antissenso/metabolismo , Fator de Transcrição Sp1/metabolismo , Adolescente , Adulto , Sequência de Bases , Proliferação de Células , Sobrevivência Celular , Células Cultivadas , Colágeno Tipo I/metabolismo , Colágeno Tipo III/metabolismo , Ensaio de Desvio de Mobilidade Eletroforética , Feminino , Fibroblastos/citologia , Humanos , Masculino , Oligonucleotídeos Antissenso/química , Oligonucleotídeos Antissenso/genética , RNA Mensageiro/metabolismo , Fator de Transcrição Sp1/genética , Transfecção , Fator de Crescimento Transformador beta/genética , Fator de Crescimento Transformador beta/metabolismo , Adulto Jovem
20.
J Org Chem ; 77(6): 2850-6, 2012 Mar 16.
Artigo em Inglês | MEDLINE | ID: mdl-22352410

RESUMO

A palladium- and copper-catalyzed tandem N-H/C-H bond functionalization reaction of ortho-(2-chlorovinyl)bromobenzenes with indoles and pyrroles has been developed. A variety of CF(3)-containing indolo- and pyrrolo[2,1-a]isoquinolines were prepared in moderate to good yields via the cyclization of 1-bromo-2-(2-chloro-3,3,3-trifluoroprop-1-enyl)benzenes with indoles and pyrroles.


Assuntos
Bromobenzenos/química , Cobre/química , Indóis/química , Indóis/síntese química , Isoquinolinas/química , Isoquinolinas/síntese química , Paládio/química , Pirróis/química , Pirróis/síntese química , Catálise , Estrutura Molecular
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