Melanogenesis inhibition by tetrahydropterines

García‐Molina, Francisco; Muñoz‐Muñoz, José Luis; Acosta, Javier; Garcı́a-Ruiz, Pedro Antonio; Tudela, José; Garcı́a-Cánovas, Francisco; Rodrı́guez-López, José Neptuno

doi:10.1016/j.bbapap.2009.08.011

Cited by 7 publications

(6 citation statements)

References 34 publications

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“…It has also been demonstrated that 6BH 4 (and their analogues) reduces o‐ dopaquinone non‐enzymatically [116, 117, 122]. The importance of 6BH 4 in melanogenesis has also been confirmed clinically in the depigmentation disorder vitiligo, where there is an excess of 6BH 4 together with its oxidation product 6‐biopterin.…”

Section: Hypothesis For New Skin‐lightening Targetsmentioning

confidence: 99%

The melanogenesis and mechanisms of skin‐lightening agents – existing and new approaches

Gillbro¹,

Olsson²

2011

Intern J of Cosmetic Sci

307

251

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SynopsisSkin-lightening products are commercially available for cosmetic purposes to obtain lighter skin complexion. Clinically, they are also used for treatment of hyperpigmentary disorders such as melasma, café au lait spot and solar lentigo. All of these target naturally melanin production, and many of the commonly used agents are known as competitive inhibitors of tyrosinase, one of the key enzymes in melanogenesis. In this review, we present an overview of commonly used skin-whitening ingredients that are commercialized, but we also hypothesize on other mechanisms that could be important targets to control skin pigmentation such as for example regulation of the adrenergic and glutaminergic signalling and also control of tetrahydrobiopterins in the human skin. Ré suméLes produits éclaircissants sont disponibles dans le commerce pour des buts cosmétiques afin d'obtenir un tient plus clair. Ils sont égale-ment utilisés en clinique, pour le traitement de troubles hyper pigmentaires comme le melasma, les taches café au lait et le lentigo solaire. Tous ces produits ont pour cible la production naturelle de mélanine et beaucoup de ceux généralement utilisés sont reconnus comme des inhibiteurs compétitifs de la tyrosinase, une des enzymes clés de la mélanogénèse. Dans cette revue, nous présentons une vue d'ensemble des ingrédients généralement utilisés et commercialisés comme blanchissant cutanés mais nous formulons aussi l'hypothèse que d'autres mécanismes pourraient être des cibles importantes pour contrôler la pigmentation de la peau comme par exemple la régula-tion du signal adrénergique et glutaminergique ou le contrôle des tetrahydrobiopterines dans la peau humaine.

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Section: Hypothesis For New Skin‐lightening Targetsmentioning

confidence: 99%

The melanogenesis and mechanisms of skin‐lightening agents – existing and new approaches

Gillbro¹,

Olsson²

2011

Intern J of Cosmetic Sci

307

251

View full text Add to dashboard Cite

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“…Under aerobic conditions, tetrahydropterines act as alternative substrates to the physiological substrates of the enzyme (L-tyrosine and L-dopa) 3 . Under such conditions, the tetrahydropterines may act as inactivators of TYR as a result of the enzyme's suicide inactivation as it acts on the substrates [4][5][6][7][8] .…”

Section: Resultsmentioning

confidence: 99%

“…for each of the isomers (Figure 4 and Table 1). Bearing in mind the values of K m S R calculated from the initial velocity measurements obtained at short times 3 , we can obtain the values of l E (max) S ox R and r (Table 1). Figure 4 In confirmation of the inactivation of tyrosinase as it acts on tetrahydropterines, Figure 5 shows the experimental values obtained for the residual diphenolase activity on TBC of the enzyme during the suicide inactivation of TYR with BH 4 .…”

Section: Experimental Study Of the Suicide Inactivationmentioning

confidence: 99%

“…In a recent work 2 , we studied the effect of tetrahydropterines at micromolar concentrations on the monophenolase and diphenolase activities of tyrosinase and demonstrated that they are oxidized by o-dopaquinone and that the systems reach the steady state when all the tetrahydropterines have been exhausted 2 . Subsequently, we demonstrated that the effect of tetrahydropterines on the catalytic activities of tyrosinase can occur at three levels: (i) through non-enzymatic inhibition, the tetrahydropterines acting as reductants of o-dopaquinone, (ii) by acting as competitive substrates of TYR and (iii) by acting as irreversible inhibitors of the enzymatic forms deoxyand met-tyrosinase 3 . Tyrosinase undergoes an inactivation process when it reacts with its phenolic substrates, a phenomenon that has long been known 4 .…”

Section: Introductionmentioning

confidence: 99%

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Suicide inactivation of tyrosinase in its action on tetrahydropterines

Muñoz‐Muñoz

García‐Molina

Garde

et al. 2011

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…9 Moreover, this antioxidant activity is pH-dependent, as recently demonstrated. 10 THF can affect the diphenolase and monophenolase activities of TYR, 16 as occurs with reduced nicotinamide adenine dinucleotide (NADH) 17 and 5,6,7,8-tetrahydrobiopterin 18 when it acts as a reductant of o-dopaquinone produced from 4-hydroxyphenylalanine (L-tyrosine) or 3,4-dihydroxyphenylalanine (L-DOPA) by TYR. As in the case of NADH 17 or 5,6,7,8-tetrahydrobiopterin, 18 THF can shorten the lag period of the monophenolase activity of TYR.…”

Section: ' Introductionmentioning

confidence: 99%

Tetrahydrofolic Acid Is a Potent Suicide Substrate of Mushroom Tyrosinase

García‐Molina

Muñoz‐Muñoz

Martı́nez-Ortiz

et al. 2011

J. Agric. Food Chem.

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The coenzyme tetrahydrofolic acid is the most rapid suicide substrate of tyrosinase that has been characterized to date. A kinetic study of the suicide inactivation process provides the kinetic constants that characterize it: λ(max), the maximum apparent inactivation constant; r, the partition ratio or the number of turnovers made by one enzyme molecule before inactivation; and k(cat) and K(m), the catalytic and Michaelis constants, respectively. From these values, it is possible to establish the ratio λ(max)/K(m), which represents the potency of the inactivation process. Besides acting as a suicide substrate of tyrosinase, tetrahydrofolic acid reduces o-quinones generated by the enzyme in its action on substrates, such as l-tyrosine and l-DOPA (o-dopaquinone), thus inhibiting enzymatic browning.

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Melanogenesis inhibition by tetrahydropterines

Cited by 7 publications

References 34 publications

The melanogenesis and mechanisms of skin‐lightening agents – existing and new approaches

The melanogenesis and mechanisms of skin‐lightening agents – existing and new approaches

Suicide inactivation of tyrosinase in its action on tetrahydropterines

Tetrahydrofolic Acid Is a Potent Suicide Substrate of Mushroom Tyrosinase

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