Cytotoxicity of dopamine-derived tetrahydroisoquinolines on melanoma cells

Marco, Federico De; Perluigi, Marzia; Marcante, Maria Luisa; Coccia, Raffaella; Foppoli, Cesira; Blarzino, Carla; Rosei, Maria Anna

doi:10.1016/s0006-2952(02)01353-9

Cited by 25 publications

(28 citation statements)

References 59 publications

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“…, and 14 A solution of compound 1 (0.6 eq) in tetrahydrofuran (THF) and a solution of tert-butyldimethylsilyl (TBS)-protected benzaldehydes (1.0 eq, compounds 3a-g) in THF were added to a stirred suspension of naH (1.5 eq) in THF and the reaction mixture was stirred at room temperature for 2-5 h. The reaction mixture was partitioned between methylene chloride and aqueous nH 4 Cl solution and the organic layers were dried, filtered, and evaporated. The residue was purified by silica gel column chromatography using hexane and etOAc (2 : 1) to give crude trienes.…”

Section: Synthesis Of Compounds 4-8 11mentioning

confidence: 99%

“…The reaction mixture was partitioned between methylene chloride and aqueous nH 4 Cl solution and the organic layers were dried, filtered, and evaporated. The residue was purified by silica gel column chromatography using hexane and etOAc (8 : 1) to give compounds 9, 10, 12, and 13.…”

Section: Synthesis Of Compounds 4-8 11mentioning

confidence: 99%

“…A solution of 15 (0.6 eq) in THF and a solution of TBS-protected benzaldehydes (1.0 eq, 3a-g) in THF were added to a stirred suspension of naH (1.5 eq) in THF and the reaction mixture was stirred at room temperature for 4-8.5 h. The reaction mixture was partitioned between methylene chloride and aqueous nH 4 Cl solution and the organic layers were dried, filtered and evaporated to give crude 1,4-bis-trans-styrylbenzenes. To a solution of crude 1,4-bis-trans-styrylbenzenes in THF and methanol (4 : 1) was added 12 n HCl and the reaction mixture was stirred at room temperature overnight.…”

Section: Synthesis Of Compounds 17-21 23 and 26mentioning

confidence: 99%

“…A solution of compound 15 (89.6 mg, 0.24 mmol) in THF (2 mL) and a solution of compound 16 (114.1 mg, 0.39 mmol) in THF (2 mL) were added to a stirred suspension of naH (23.7 mg, 0.59 mmol) in THF (2 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was partitioned between methylene chloride and aqueous nH 4 Cl solution and the organic layers were dried, filtered and evaporated to give crude 1,4-bistrans-styrylbenzenes. Hydrogen chloride (12 n) was added to a solution of crude 1,4-bis-trans-styrylbenzenes in THF (2 mL) and methanol (1 mL) and the reaction mixture was stirred at room temperature for 2 d. The precipitates generated were filtered and washed with water and methylene chloride and hexane (2 : 1) to give compound 27.…”

Section: Synthesis Of Compound 27mentioning

confidence: 99%

“…1,2) Recently, it has also been reported that secretion of neuronal tyrosinase plays an important role in anti apoptosis. 3) Hence, over-expression of tyrosinase in brain might either be toxic, because of increased melanin precursors such as 3,4-dihydroxyphenylalanine (DOPA) and dopaquinone, 4) or neuroprotective, because of the formation of neuromelanin. 5) Tyrosinase has been also linked to Parkinson's and other neurodegenerative diseases.…”

mentioning

confidence: 99%

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Molecular Docking Studies of (1E,3E,5E)-1,6-Bis(substituted phenyl)hexa-1,3,5-triene and 1,4-Bis(substituted trans-styryl)benzene Analogs as Novel Tyrosinase Inhibitors

Lee

Park

et al. 2013

Biological & Pharmaceutical Bulletin

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We simulated the docking of the tertiary structure of mushroom tyrosinase with our compounds. From the structure-tyrosinase inhibitory activity relationship, it is notable that compounds 4, 8 and 11 showed similar or better activity rates than kojic acid which was used as a positive control. Compounds 17, 21, and 23 among benzene analogs that possess the same substituent showed significantly lower tyrosinase inhibitory effects. Therefore, we have confirmed that among the compounds showing better tyrosinase inhibitory effects than kojic acid, the compounds with triene analogs have better tyrosinase inhibitory effect than the compounds with benzene analogs. Docking simulation suggested the mechanism of compounds by several key residues which had possible hydrogen bonding interactions. The pharmacophore model underlined the features of active compounds, 4,4′-((1E,3E,5E)-hexa-1,3,5-triene-1,6-diyl)diphenol, 5,5′-((1E,3E,5E)-hexa-1,3,5-triene-1,6-diyl)bis(2-methoxy-phenol), and 5,5′-((1E,3E,5E)-hexa-1,3,5-triene-1,6-diyl)dibenzene-1,3-diol among triene derivatives which had several hydrogen bond groups on both terminal rings. The soundness of the docking results and the agreement with the pharmacophores suggest that it can be conveniently exploited to design inhibitors with an improved affinity for tyrosinase.

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Section: Synthesis Of Compounds 4-8 11mentioning

confidence: 99%

Section: Synthesis Of Compounds 4-8 11mentioning

confidence: 99%

Section: Synthesis Of Compounds 17-21 23 and 26mentioning

confidence: 99%

Section: Synthesis Of Compound 27mentioning

confidence: 99%

mentioning

confidence: 99%

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Molecular Docking Studies of (1E,3E,5E)-1,6-Bis(substituted phenyl)hexa-1,3,5-triene and 1,4-Bis(substituted trans-styryl)benzene Analogs as Novel Tyrosinase Inhibitors

Lee

Park

et al. 2013

Biological & Pharmaceutical Bulletin

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Tetrahydropapaveroline, an Endogenous Dicatechol Isoquinoline Neurotoxin

Surh

Kim

2009

Endogenous Toxins

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The association between Parkinson's disease and melanoma

Pan

Jankovic

2011

Intl Journal of Cancer

142

138

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Parkinson's disease (PD) is a neurodegenerative disorder characterized by a loss of melanin-positive, dopaminergic neurons in the substantia nigra. Although there is convincing epidemiologic evidence of a negative association between PD and most cancers, a notable exception to this is that melanoma, a malignant tumor of melanin-producing cells in skin, occurs with higher-than-expected frequency among subjects with PD and that melanoma patients are more likely to have PD. A clear biological explanation for this epidemiological observation is lacking. Here, we present a comprehensive review of published literature exploring the association between PD and melanoma. On the basis of published findings, we conclude that (i) changes in pigmentation including melanin synthesis and/or melanin synthesis enzymes, such as tyrosinase and tyrosine hydroxylase, play important roles in altered vulnerability for both PD and melanoma; (ii) changes of PD-related genes such as Parkin, LRRK2 and a-synuclein may increase the risk of melanoma; (iii) changes in some low-penetrance genes such as cytochrome p450 debrisoquine hydroxylase locus, glutathione S-transferase M1 and vitamin D receptor could increase the risk for both PD and melanoma and (iv) impaired autophagy in both PD and melanoma could also explain the association between PD and melanoma. Future studies are required to address whether altered pigmentation, PD-or melanoma-related gene changes and/or changes in autophagy function induce oncogenesis or apoptosis. From a clinical point of view, early diagnosis of melanoma in PD patients is critical and can be enhanced by periodic dermatological surveillance, including skin biopsies.Parkinson's disease (PD) is a neurodegenerative disorder, characterized by a striking loss of melanin-positive, dopaminergic neurons in the substantia nigra pars compacta (SNpc) accompanied by depletion of dopamine (DA) in the striatum and the presence of cytoplasmic inclusions known as Lewy bodies (LBs), composed predominantly of fibrillar a-synuclein. 1,2 Cancer, also called malignancy, is not just one disease, but a large group of diseases whose two main characteristics are uncontrolled growth of the cells in the human body and the ability of these cells to migrate from the original site and spread to distant sites (metastasis), which can result in death if not controlled.Although PD and cancer are two distinct diseases that result from abnormal signaling by seemingly opposite forces that drive the cells to either degeneration or overproliferation respectively, the association of PD and cancer has recently attracted much interest. [3][4][5][6] The PD-cancer link has been supported by a number of well-designed epidemiologic studies. These studies have shown that most cancer rates are lower in patients with PD compared to those in the general population, and that the risk of dying from cancer is lower in PD patients than in the general population, indicating that PD provides some type of ''biologic protection'' against certain types of cancers. Howe...

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Cytotoxicity of dopamine-derived tetrahydroisoquinolines on melanoma cells

Cited by 25 publications

References 59 publications

Molecular Docking Studies of (1<i>E</i>,3<i>E</i>,5<i>E</i>)-1,6-Bis(substituted phenyl)hexa-1,3,5-triene and 1,4-Bis(substituted <i>trans</i>-styryl)benzene Analogs as Novel Tyrosinase Inhibitors

Molecular Docking Studies of (1<i>E</i>,3<i>E</i>,5<i>E</i>)-1,6-Bis(substituted phenyl)hexa-1,3,5-triene and 1,4-Bis(substituted <i>trans</i>-styryl)benzene Analogs as Novel Tyrosinase Inhibitors

Tetrahydropapaveroline, an Endogenous Dicatechol Isoquinoline Neurotoxin

The association between Parkinson's disease and melanoma

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