4-(Phenylsulfanyl)butan-2-One Suppresses Melanin Synthesis and Melanosome Maturation In Vitro and In Vivo

Overview

Journal Int J Mol Sci

Publisher MDPI

Specialties Biochemistry
Chemistry
Molecular Biology

Date 2015 Sep 8

PMID 26343635

Citations 21

Authors

Shing-Yi Sean Wu

Hui-Min David Wang

Yi-Shan Wen

Wangta Liu

Pin-Hui Li

Chien-Chih Chiu

Pei-Chin Chen

Chiung-Yao Huang

Jyh-Horng Sheu

Zhi-Hong Wen

Affiliations

Soon will be listed here.

Abstract

In this study, we screened compounds with skin whitening properties and favorable safety profiles from a series of marine related natural products, which were isolated from Formosan soft coral Cladiella australis. Our results indicated that 4-(phenylsulfanyl)butan-2-one could successfully inhibit pigment generation processes in mushroom tyrosinase platform assay, probably through the suppression of tyrosinase activity to be a non-competitive inhibitor of tyrosinase. In cell-based viability examinations, it demonstrated low cytotoxicity on melanoma cells and other normal human cells. It exhibited stronger inhibitions of melanin production and tyrosinase activity than arbutin or 1-phenyl-2-thiourea (PTU). Also, we discovered that 4-(phenylsulfanyl)butan-2-one reduces the protein expressions of melanin synthesis-related proteins, including the microphthalmia-associated transcription factor (MITF), tyrosinase-related protein-1 (Trp-1), dopachrome tautomerase (DCT, Trp-2), and glycoprotein 100 (GP100). In an in vivo zebrafish model, it presented a remarkable suppression in melanogenesis after 48 h. In summary, our in vitro and in vivo biological assays showed that 4-(phenylsulfanyl)butan-2-one possesses anti-melanogenic properties that are significant in medical cosmetology.

Citing Articles

Zebrafish in dermatology: a comprehensive review of their role in investigating abnormal skin pigmentation mechanisms.

Qu J, Yan M, Fang Y, Zhao J, Xu T, Liu F Front Physiol. 2023; 14:1296046.

PMID: 38074315 PMC: 10702362. DOI: 10.3389/fphys.2023.1296046.

Transglutaminase Type 2-MITF axis regulates phenotype switching in skin cutaneous melanoma.

Muccioli S, Brillo V, Varanita T, Rossin F, Zaltron E, Velle A Cell Death Dis. 2023; 14(10):704.

PMID: 37898636 PMC: 10613311. DOI: 10.1038/s41419-023-06223-y.

Naturally-Occurring Tyrosinase Inhibitors Classified by Enzyme Kinetics and Copper Chelation.

Kim H, Choi H, Abekura F, Park J, Yang W, Yang S Int J Mol Sci. 2023; 24(9).

PMID: 37175965 PMC: 10178891. DOI: 10.3390/ijms24098226.

Enzyme Inhibitors from Gorgonians and Soft Corals.

Cordova-Isaza A, Jimenez-Marmol S, Guerra Y, Salas-Sarduy E Mar Drugs. 2023; 21(2).

PMID: 36827145 PMC: 9963996. DOI: 10.3390/md21020104.

Suppressive Effects of 4-(Phenylsulfanyl) Butan-2-One on CCL-1 Production via Histone Acetylation in Monocytes.

Tsai M, Tsai M, Wen Z, Liao W, Lin Y, Chiou H Curr Issues Mol Biol. 2022; 44(10):4616-4625.

PMID: 36286030 PMC: 9600508. DOI: 10.3390/cimb44100315.

References

Wang H, Chen C, Wen Z . Identifying melanogenesis inhibitors from Cinnamomum subavenium with in vitro and in vivo screening systems by targeting the human tyrosinase. Exp Dermatol. 2010; 20(3):242-8. DOI: 10.1111/j.1600-0625.2010.01161.x. View

Cheng S, Huang Liu R, Sheu J, Chen S, Sinchaikul S, Tsay G . Toxicogenomics of kojic acid on gene expression profiling of a375 human malignant melanoma cells. Biol Pharm Bull. 2006; 29(4):655-69. DOI: 10.1248/bpb.29.655. View

Malafoglia V, Bryant B, Raffaeli W, Giordano A, Bellipanni G . The zebrafish as a model for nociception studies. J Cell Physiol. 2013; 228(10):1956-66. DOI: 10.1002/jcp.24379. View

Slominski A, Moellmann G, Kuklinska E . L-tyrosine, L-dopa, and tyrosinase as positive regulators of the subcellular apparatus of melanogenesis in Bomirski Ab amelanotic melanoma cells. Pigment Cell Res. 1989; 2(2):109-16. DOI: 10.1111/j.1600-0749.1989.tb00170.x. View

Feng C, Wen Z, Huang S, Hung H, Chen C, Yang S . Effects of 6-hydroxydopamine exposure on motor activity and biochemical expression in zebrafish (Danio rerio) larvae. Zebrafish. 2014; 11(3):227-39. PMC: 4050718. DOI: 10.1089/zeb.2013.0950. View

Wen Z, Chao C, Wu M, Sheu J . A neuroprotective sulfone of marine origin and the in vivo anti-inflammatory activity of an analogue. Eur J Med Chem. 2010; 45(12):5998-6004. DOI: 10.1016/j.ejmech.2010.09.067. View

Li W, Lin Y, Wu P, Wen Z, Liu P, Chen C . Biofunctional constituents from Liriodendron tulipifera with antioxidants and anti-melanogenic properties. Int J Mol Sci. 2013; 14(1):1698-712. PMC: 3565342. DOI: 10.3390/ijms14011698. View

Hoashi T, Watabe H, Muller J, Yamaguchi Y, Vieira W, Hearing V . MART-1 is required for the function of the melanosomal matrix protein PMEL17/GP100 and the maturation of melanosomes. J Biol Chem. 2005; 280(14):14006-16. DOI: 10.1074/jbc.M413692200. View

Hemesath T, Steingrimsson E, McGill G, Hansen M, VAUGHT J, Hodgkinson C . microphthalmia, a critical factor in melanocyte development, defines a discrete transcription factor family. Genes Dev. 1994; 8(22):2770-80. DOI: 10.1101/gad.8.22.2770. View

10.

Kelsh R, Brand M, Jiang Y, Heisenberg C, Lin S, Haffter P . Zebrafish pigmentation mutations and the processes of neural crest development. Development. 1996; 123:369-89. DOI: 10.1242/dev.123.1.369. View

11.

Logan D, Burn S, Jackson I . Regulation of pigmentation in zebrafish melanophores. Pigment Cell Res. 2006; 19(3):206-13. DOI: 10.1111/j.1600-0749.2006.00307.x. View

12.

Duval C, Cohen C, Chagnoleau C, Flouret V, Bourreau E, Bernerd F . Key regulatory role of dermal fibroblasts in pigmentation as demonstrated using a reconstructed skin model: impact of photo-aging. PLoS One. 2014; 9(12):e114182. PMC: 4260844. DOI: 10.1371/journal.pone.0114182. View

13.

Jacobsohn G, Jacobsohn M . Incorporation and binding of estrogens into melanin: comparison of mushroom and mammalian tyrosinases. Biochim Biophys Acta. 1992; 1116(2):173-82. DOI: 10.1016/0304-4165(92)90114-a. View

14.

Bertolotto C, Abbe P, Hemesath T, Bille K, Fisher D, Ortonne J . Microphthalmia gene product as a signal transducer in cAMP-induced differentiation of melanocytes. J Cell Biol. 1998; 142(3):827-35. PMC: 2148160. DOI: 10.1083/jcb.142.3.827. View

15.

Bin B, Bhin J, Yang S, Choi D, Park K, Shin D . Hyperosmotic stress reduces melanin production by altering melanosome formation. PLoS One. 2014; 9(8):e105965. PMC: 4149489. DOI: 10.1371/journal.pone.0105965. View

16.

Chiu C, Chou H, Wu P, Chen H, Wang H, Chen C . Bio-functional constituents from the stems of Liriodendron tulipifera. Molecules. 2012; 17(4):4357-72. PMC: 6268983. DOI: 10.3390/molecules17044357. View

17.

Chen W, Chakraborty C, Sung C, Feng C, Jean Y, Lin Y . Neuroprotection by marine-derived compound, 11-dehydrosinulariolide, in an in vitro Parkinson's model: a promising candidate for the treatment of Parkinson's disease. Naunyn Schmiedebergs Arch Pharmacol. 2011; 385(3):265-75. DOI: 10.1007/s00210-011-0710-2. View

18.

Lo C, Liu P, Lin L, Chen Y, Hseu Y, Wen Z . Antimelanoma and antityrosinase from Alpinia galangal constituents. ScientificWorldJournal. 2013; 2013:186505. PMC: 3763262. DOI: 10.1155/2013/186505. View

19.

Love D, Pichler F, Dodd A, Copp B, Greenwood D . Technology for high-throughput screens: the present and future using zebrafish. Curr Opin Biotechnol. 2004; 15(6):564-71. DOI: 10.1016/j.copbio.2004.09.004. View

20.

Slominski A, Moellmann G, Kuklinska E, BOMIRSKI A, Pawelek J . Positive regulation of melanin pigmentation by two key substrates of the melanogenic pathway, L-tyrosine and L-dopa. J Cell Sci. 1988; 89 ( Pt 3):287-96. DOI: 10.1242/jcs.89.3.287. View