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The Potential of 2-Aza-8-Oxohypoxanthine As a Cosmetic Ingredient

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The Potential of 2-Aza-8-Oxohypoxanthine As a Cosmetic Ingredient cosmetics Article The Potential of 2-aza-8-Oxohypoxanthine as a Cosmetic Ingredient Hisae Aoshima 1,*, Masayuki Ito 1, Rinta Ibuki 1 and Hirokazu Kawagishi 2,3,4,* 1 Department of Research and Development, Vitamin C60 BioResearch Corp, Nihonbashidori-Nichoume Bldg, 4F 2-2-6 Nihonbashi Chuo-ku, Tokyo 103-0027, Japan; [email protected] (M.I.); [email protected] (R.I.) 2 Research Institute of Green Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan 3 Graduate School of Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan 4 Graduate School of Integrated Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka 422-8529, Japan * Correspondence: [email protected] (H.A.); [email protected] (H.K.) Abstract: In this study, we verified the effects of 2-aza-8-oxohypoxanthine (AOH) on human epi- dermal cell proliferation by performing DNA microarray analysis. Cell proliferation was assessed using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, which measures mito- chondrial respiration in normal human epidermal keratinocyte (NHEK) cells. Gene expression levels were determined by DNA microarray analysis of 177 genes involved in skin aging and disease. AOH showed a significant increase in cell viability at concentrations between 7.8 and 31.3 µg/mL and a significant decrease at concentrations above 250 µg/mL. DNA microarray analysis showed that Citation: Aoshima, H.; Ito, M.; Ibuki, AOH significantly increased the gene expression of CLDN1, DSC1, DSG1, and CDH1 (E-cadherin), R.; Kawagishi, H. The Potential of which are involved in intercellular adhesion and skin barrier functioning. AOH also up-regulated 2-aza-8-Oxohypoxanthine as a the expression of KLK5, KLK7, and SPIMK5, which are proteases involved in stratum corneum Cosmetic Ingredient. Cosmetics 2021, detachment. Furthermore, AOH significantly stimulated the expression of KRT1, KRT10, TGM1, 8, 60. https://doi.org/10.3390/ and IVL, which are considered general differentiation indicators, and that of SPRR1B, a cornified cosmetics8030060 envelope component protein. AOH exerted a cell activation effect on human epidermal cells. Since AOH did not cause cytotoxicity, it was considered that the compound had no adverse effects on the Academic Editors: skin. In addition, it was found that AOH stimulated the expression levels of genes involved in skin Mohamad Goldust, Martin Kassir and George Kroumpouzos barrier functioning by DNA microarray analysis. Therefore, AOH has the potential for practical use as a cosmetic ingredient. This is the first report of efficacy evaluation tests performed for AOH. Received: 20 May 2021 Accepted: 22 June 2021 Keywords: fairy chemical; 2-aza-8-oxohypoxanthine; microarray analysis; skin barrier function Published: 25 June 2021 Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in 1. Introduction published maps and institutional affil- Turfgrass occasionally grows in the shape of a ring, with thicker growth than the iations. surrounding grass, and thereafter, mushrooms form in the same circle (Figure1). This phenomenon, which occurs on lawns in parks and golf courses, is called “fairy rings.” In Western legend, it is said that fairies make these circles and dance inside of them [1–3]. Since the first paper on “fairy rings” published in 1675 and the subsequent papers were Copyright: © 2021 by the authors. introduced in Nature in 1875, the cause of the phenomenon had remained a mystery for Licensee MDPI, Basel, Switzerland. a long time until our finding on “fairy chemicals” [4]. We cultured the hyphae of one of This article is an open access article the fairy-ring-forming fungi, Lepista sordida, and discovered a plant growth stimulator, distributed under the terms and 2-azahypoxanthine (AHX), in the culture broth. We also found imidazole-4-carboxamide conditions of the Creative Commons (ICA), which suppressed the growth of turfgrass from the broth [5,6]. Furthermore, it Attribution (CC BY) license (https:// has been revealed that AHX was converted into 2-aza-8-oxohypoxanthine (AOH) when creativecommons.org/licenses/by/ absorbed into plants (Figure2)[ 7]. We named AHX, ICA, and AOH as fairy chemicals 4.0/). Cosmetics 2021, 8, 60. https://doi.org/10.3390/cosmetics8030060 https://www.mdpi.com/journal/cosmetics Cosmetics 2021, 8, x FOR PEER REVIEW 2 of 9 Cosmetics 2021, 8, x FOR PEER REVIEW 2 of 9 Cosmetics 2021, 8, 60 2 of 8 been revealed that AHX was converted into 2-aza-8-oxohypoxanthine (AOH) when ab- sorbed into plants (Figure 2) [7]. We named AHX, ICA, and AOH as fairy chemicals (FCs) afterbeen the revealed title of that the AHXarticle w inas Natureconverted that into covered 2-aza -our8-oxohypoxanthine study [8]. Subsequent (AOH) studieswhen ab- have sorbed(FCs) into after plants the title (Figure of the 2) article [7]. We in Nature namedthat AHX, covered ICA, our and study AOH [ 8as]. Subsequentfairy chemicals studies (FCs) demonstratedhave demonstrated that FCs that endogenously FCs endogenously exist existin all in the all theplants plants tested, tested, including including edible edible parts ofafter three the major title of cereal the article crops, in rice,Nature wheat, that coveredand corn our [7]; study thus, [8]. people Subsequent have eatenstudies FCs have for a demonstratedparts of three that major FCs cereal endogenously crops, rice, wheat,exist in and all cornthe plants [7]; thus, tested, people including have eaten edible FCs forparts longa longtime. time. Furthermore, Furthermore, FCs FCs increased increased the the yieldsof of rice, rice, wheat, wheat, and and other other crops crops under under of three major cereal crops, rice, wheat, and corn [7]; thus, people have eaten FCs for a fieldfield and and greenhouse greenhouse conditions conditions [[5,9,105,9,10].]. These These results results suggest suggest that that FCs FCs are aare new a new family family long time. Furthermore, FCs increased the yields of rice, wheat, and other crops under of plantof plant hormones hormones [11,12 [11,12].]. field and greenhouse conditions [5,9,10]. These results suggest that FCs are a new family of plant hormones [11,12]. Figure 1. FigureFairy rings 1. Fairy appearing rings appearing on golf on course golf course grass. grass. Figure 1. Fairy rings appearing on golf course grass. FigureFigureFigure 2. 2.Structures Structures 2. Structures of of (a of()a ) (2 a-2)azahypoxanthine- 2-azahypoxanthineazahypoxanthine (AHX),(AHX), (AHX), ( (bb)) imidazole imidazole-4-carboxamideimidazole-4-4-carboxamide-carboxamide (ICA),(ICA), (ICA), ( c()c 2-aza-8-oxohypoxanthine)( c2)- aza2-aza-8--oxohypoxanthine8-oxohypoxanthine (AOH),(AOH),(AOH), and and kinetin. and kinetin. kinetin. Kinetin (N6-furfuryladenine) is a member of the cytokinin plant growth hormone KinetinKinetin (N6(N6--furfuryladenine)furfuryladenine) isis aa membermember of of the the cytokinin cytokinin plant plant growth growth hormone hormone familyfamily and and is isknown known for for its its growth growth-promoting-promoting and anti-aginganti-aging effects effects on on plants plants (Figure (Figure2). 2). familyStanley and B. is Levy known of the for Revlon its growth Consumer-promoting Products and Corporation anti-aging stated effects that on kinetin plants is(Figure also 2). Stanley B. Levy of the Revlon Consumer Products Corporation stated that kinetin is also Stanleyuseful B. against Levy humanof the Revlon skin aging Consumer [13]. Many Pro studiesducts have Corporation reported the stated anti-aging that kinetin effects of is also useful against human skin aging [13]. Many studies have reported the anti-aging effects usefulkinetin against on human human skin skin cells aging in clinical [13]. trials Many [14 –studies18]. Therefore, have reported kinetin is the currently anti-aging used aseffects of kinetin on human skin cells in clinical trials [14–18]. Therefore, kinetin is currently used of kinetinan ingredient on human in cosmetics skin cells and in cosmeceuticals. clinical trials [14 Similar–18]. to Therefore, kinetin, FCs kinetin also have is currently a purine used as an ingredient in cosmetics and cosmeceuticals. Similar to kinetin, FCs also have a pu- as ancarbon ingredient skeleton in (Figure cosmet2)ics and and regulate cosmeceuticals. plant growth. Similar Therefore, to kinetin, we thought FCs also that have FCs a pu- rine carbon skeleton (Figure 2) and regulate plant growth. Therefore, we thought that FCs rinemight carbon have skeleton similar ( effectsFigure to 2) kinetin and regulate on human plant skin growth. cells and Therefore, examined them.we thought First of that all, FCs mightthe safety have ofsimilar FCs was effects evaluated. to kinetin AOH on yieldedhuman theskin best cells result and andexamined showed them. no toxicity First of in all, mightthe safety have of similar FCs was effects evaluated. to kinetin AOH on yielded human the skin best cells result and and examined showed them. no toxicity First of in all, the safety of FCs was evaluated. AOH yielded the best result and showed no toxicity in Cosmetics 2021, 8, 60 3 of 8 any of the safety evaluations for cosmetic applications, including Ames test, skin irritation, skin sensitization (DPRA), in vitro phototoxicity tests, and human patch tests [19]. In this study, we focused on AOH and evaluated the viability of normal human epidermal keratinocyte (NHEK) cells to verify the potential of AOH as a cosmetic ingredient. In addition, DNA microarray analysis was performed to analyze the effects of AOH on the skin comprehensively. 2. Materials and Methods 2.1. Chemicals and Reagents AOH was synthesized from 5-aminoimidazole-4-carboxamide as previously described [7,20,21]. NHEKs (Kurabo Industries Ltd., Osaka, Japan) were cultured in HuMedia KG2 (KG2) and HuMedia KB2 (KB2) media (Kurabo Industries Ltd.). 3-(4,5- dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and 2-propanol were pur- chased from Kanto Chemical Co., Inc. (Tokyo, Japan). QIAzol Lysis Reagent and an miRNeasy Mini Kit were purchased from QIAGEN (Hilden, Germany).
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