Inhibitory Effect of Chlorogenic Acid Analogues Comprising Pyridine and Pyrimidine on α-MSH-Stimulated Melanogenesis and Stability of Acyl Analogues in Methanol

In continuation of studies for α-MSH stimulated melanogenesis inhibitors, we have evaluated the design, synthesis, and activity of a new series of chlorogenic acid (CGA) analogues comprising pyridine, pyrimidine, and diacyl derivatives. Among nineteen synthesized compounds, most of them (fifteen) ex...

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Autores principales:	Jaeuk Sim, Srinu Lanka, Jeong-Woong Jo, Chhabi Lal Chaudhary, Manjunatha Vishwanath, Chan-Hyun Jung, Young-Hee Lee, Eun-Yeong Kim, Young-Soo Kim, Soon-Sil Hyun, Hee-Soon Lee, Kiho Lee, Seung-Yong Seo, Mayavan Viji, Jae-Kyung Jung
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	chlorogenic acid α-MSH-stimulated melanogenesis pyridine pyrimidine B16 melanoma cells Medicine R Pharmacy and materia medica RS1-441
Acceso en línea:	https://doaj.org/article/6843a113b5784cb0822c810df0f438c9
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spelling	oai:doaj.org-article:6843a113b5784cb0822c810df0f438c92021-11-25T18:39:56ZInhibitory Effect of Chlorogenic Acid Analogues Comprising Pyridine and Pyrimidine on α-MSH-Stimulated Melanogenesis and Stability of Acyl Analogues in Methanol10.3390/ph141111761424-8247https://doaj.org/article/6843a113b5784cb0822c810df0f438c92021-11-01T00:00:00Zhttps://www.mdpi.com/1424-8247/14/11/1176https://doaj.org/toc/1424-8247In continuation of studies for α-MSH stimulated melanogenesis inhibitors, we have evaluated the design, synthesis, and activity of a new series of chlorogenic acid (CGA) analogues comprising pyridine, pyrimidine, and diacyl derivatives. Among nineteen synthesized compounds, most of them (fifteen) exhibited better inhibitions of melanin formation in B16 melanoma cells. The results illustrated that a pyridine analogue <b>6f</b> and a diacyl derivative <b>13a</b> of CGA showed superior inhibition profiles (IC<sub>50</sub>: 2.5 ± 0.7 μM and 1.1 ± 0.1 μM, respectively) of <i>α</i>-MSH activities than positive controls, kojic acid and arbutin (IC<sub>50</sub>: 54 ± 1.5 μM and 380 ± 9.5 μM, respectively). The SAR studies showed that both –CF<sub>3</sub> and –Cl groups exhibited better inhibition at the <i>meta</i> position on benzylamine than their <i>ortho</i> and <i>para</i> positions. In addition, the stability of diacyl analogues of CGA in methanol monitored by HPLC for 28 days indicated the steric bulkiness of acyl substituents as a key factor in their stability.Jaeuk SimSrinu LankaJeong-Woong JoChhabi Lal ChaudharyManjunatha VishwanathChan-Hyun JungYoung-Hee LeeEun-Yeong KimYoung-Soo KimSoon-Sil HyunHee-Soon LeeKiho LeeSeung-Yong SeoMayavan VijiJae-Kyung JungMDPI AGarticlechlorogenic acidα-MSH-stimulated melanogenesispyridinepyrimidineB16 melanoma cellsMedicineRPharmacy and materia medicaRS1-441ENPharmaceuticals, Vol 14, Iss 1176, p 1176 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	chlorogenic acid α-MSH-stimulated melanogenesis pyridine pyrimidine B16 melanoma cells Medicine R Pharmacy and materia medica RS1-441
spellingShingle	chlorogenic acid α-MSH-stimulated melanogenesis pyridine pyrimidine B16 melanoma cells Medicine R Pharmacy and materia medica RS1-441 Jaeuk Sim Srinu Lanka Jeong-Woong Jo Chhabi Lal Chaudhary Manjunatha Vishwanath Chan-Hyun Jung Young-Hee Lee Eun-Yeong Kim Young-Soo Kim Soon-Sil Hyun Hee-Soon Lee Kiho Lee Seung-Yong Seo Mayavan Viji Jae-Kyung Jung Inhibitory Effect of Chlorogenic Acid Analogues Comprising Pyridine and Pyrimidine on α-MSH-Stimulated Melanogenesis and Stability of Acyl Analogues in Methanol
description	In continuation of studies for α-MSH stimulated melanogenesis inhibitors, we have evaluated the design, synthesis, and activity of a new series of chlorogenic acid (CGA) analogues comprising pyridine, pyrimidine, and diacyl derivatives. Among nineteen synthesized compounds, most of them (fifteen) exhibited better inhibitions of melanin formation in B16 melanoma cells. The results illustrated that a pyridine analogue <b>6f</b> and a diacyl derivative <b>13a</b> of CGA showed superior inhibition profiles (IC<sub>50</sub>: 2.5 ± 0.7 μM and 1.1 ± 0.1 μM, respectively) of <i>α</i>-MSH activities than positive controls, kojic acid and arbutin (IC<sub>50</sub>: 54 ± 1.5 μM and 380 ± 9.5 μM, respectively). The SAR studies showed that both –CF<sub>3</sub> and –Cl groups exhibited better inhibition at the <i>meta</i> position on benzylamine than their <i>ortho</i> and <i>para</i> positions. In addition, the stability of diacyl analogues of CGA in methanol monitored by HPLC for 28 days indicated the steric bulkiness of acyl substituents as a key factor in their stability.
format	article
author	Jaeuk Sim Srinu Lanka Jeong-Woong Jo Chhabi Lal Chaudhary Manjunatha Vishwanath Chan-Hyun Jung Young-Hee Lee Eun-Yeong Kim Young-Soo Kim Soon-Sil Hyun Hee-Soon Lee Kiho Lee Seung-Yong Seo Mayavan Viji Jae-Kyung Jung
author_facet	Jaeuk Sim Srinu Lanka Jeong-Woong Jo Chhabi Lal Chaudhary Manjunatha Vishwanath Chan-Hyun Jung Young-Hee Lee Eun-Yeong Kim Young-Soo Kim Soon-Sil Hyun Hee-Soon Lee Kiho Lee Seung-Yong Seo Mayavan Viji Jae-Kyung Jung
author_sort	Jaeuk Sim
title	Inhibitory Effect of Chlorogenic Acid Analogues Comprising Pyridine and Pyrimidine on α-MSH-Stimulated Melanogenesis and Stability of Acyl Analogues in Methanol
title_short	Inhibitory Effect of Chlorogenic Acid Analogues Comprising Pyridine and Pyrimidine on α-MSH-Stimulated Melanogenesis and Stability of Acyl Analogues in Methanol
title_full	Inhibitory Effect of Chlorogenic Acid Analogues Comprising Pyridine and Pyrimidine on α-MSH-Stimulated Melanogenesis and Stability of Acyl Analogues in Methanol
title_fullStr	Inhibitory Effect of Chlorogenic Acid Analogues Comprising Pyridine and Pyrimidine on α-MSH-Stimulated Melanogenesis and Stability of Acyl Analogues in Methanol
title_full_unstemmed	Inhibitory Effect of Chlorogenic Acid Analogues Comprising Pyridine and Pyrimidine on α-MSH-Stimulated Melanogenesis and Stability of Acyl Analogues in Methanol
title_sort	inhibitory effect of chlorogenic acid analogues comprising pyridine and pyrimidine on α-msh-stimulated melanogenesis and stability of acyl analogues in methanol
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/6843a113b5784cb0822c810df0f438c9
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Inhibitory Effect of Chlorogenic Acid Analogues Comprising Pyridine and Pyrimidine on α-MSH-Stimulated Melanogenesis and Stability of Acyl Analogues in Methanol

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