• YAKHAK HOEJI
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• v.38 no.3
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• pp.230-237
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• 1994

The structure-activity relationships of (E)-chalcone-4-carboxylic acids, flavone-4'-carboxylic acids, two types of aromatic amides, terephthalic monoanilides, and (arylcarboxamido)benzoic acids, which were made by Shudo group, are discussed by conformation analysis(AM1) of retinoic acid and those compounds. Conformer of each compound is superimposed on the conformationally restricted compound, 4-(6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-4-oxonaphto[ 2,3-b]pyran-2-yl) benzoic acid(Fv80), possessing the strongest differentiation-inducing activity on human promyelocytic leukemia cells HL-60. The results indicated that the lengths between the carboxylic carbon and the two 6, 9 carbons binding to dimethyl, 1.20 nm and 1.09 nm, as well as the planarity of molecule are very important factors for the activity, especially 1.20 nm. In the case of the recently synthesized azulenic retinoic acids by Sato, et al. in 1993, the distance probably is also important, resulted from superimposing them on a Ch55 conformer and Fv80. The distance 1.0 nm is also important in Ch55. Several conformers of all-trans retinoic acid (RA) are well superimposed on the almost non-flexible Fv80, RA, 9-cis RA, and, specifically s-10,12 cis RA. And a simple hexangular model of RA is suggested to draw RA conformers easily without computer drawing model or molecular model.

• Bulletin of the Korean Chemical Society
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• v.22 no.6
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• pp.581-586
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• 2001

The potential anticancer agents, new anthracycline analogues (2-9) have been synthesized from the glycosides daunomycin (1a) and doxorubicin (1b). Compounds 2 and 6 were prepared by nucleophilic displacement esterification of a 14-bromodauomycin(1c) with sodium or potassium salts of butyric and all trans retinoic acid, respectively. Compounds 3 and 7 were obtained from daunomycin (1a) by direct amidation with a butyric and all trans retinoic acid in the presence of EDCI and PP, respectively. Compounds 4 and 8 were obtained from doxorubicin (1b) by reaction with the corresponding acids in the same manner. Compounds 5 and 9 were prepared from doxorubicin (1b) by acylation with two equivalents of the corresponding acids under the same reaction conditions.

• Journal of the Society of Cosmetic Scientists of Korea
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• v.42 no.4
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• pp.433-440
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• 2016

In this study, a poly (amino acid)s derivative grafted with retinoic acids, which could form self-assemblies in an aqueous solution, was successfully synthesized. The synthesized amphiphilic poly (amino acid)s were controlled with 5, 10, 30 mol% substitution of retinoic acid. Then, the amphiphilic poly (amino acid)s were self-assembled by inter/intra molecular stacking of retinoic acids in an aqueous solution. Also, the increasing the degree of substitution (DS) of retinoic acids decreased the size of self-assembled nanoparticles and induced structural transition to bilayer structure from spherical structure. The retinol was stably encapsulated into a core of self-assembled nanoparticle with 10 mol% of DS. This strategy to prepare the self-assemblies of amphiphilic polyaspartamide will serve to improve the efficiency of targeted delivery for a functional cosmetic with various biological modalities.

• Proceedings of the Korea Environmental Mutagen Society Conference
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• 2004.11a
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• pp.142-142
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• 2004

• Proceedings of the Korea Environmental Mutagen Society Conference
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• 2004.05a
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• pp.99-99
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• 2004

• Asian-Australasian Journal of Animal Sciences
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• v.31 no.3
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• pp.439-448
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• 2018

Objective: Myogenic satellite cells were isolated from semitendinosus muscle of prepubertal Korean black goat to observe the differential effect of linolenic and retinoic acid in thepresence of thiazolidinediones (TZD) and also to observe the production insulin sensitive preadipocyte. Methods: Cells were characterized for their stemness with cluster of differentiation 34 (CD34), CD13, CD106, CD44, Vimentin surface markers using flow cytometry. Cells characterized themselves as possessing significant (p<0.05) levels of CD13, CD34, CD106, Vimentin revealing their stemness potential. Goat myogenic satellite cells also exhibited CD44, indicating that they possessed a % of stemness factors of adipose lineage apart from their inherent stemness of paxillin factors 3/7. Results: Cells during proliferation stayed absolutely and firmly within the myogenic fate without any external cues and continued to show a significant (p<0.05) fusion index % to express myogenic differentiation, myosin heavy chain, and smooth muscle actin in 2% horse serum. However, confluent myogenic satellite cells were the ones easily turning into adipogenic lineage. Intriguingly, upregulation in adipose specific genetic markers such as peroxisome proliferation-activated receptor ${\gamma}$, adiponectin, lipoprotein lipase, and CCAAT/enhancer binding protein ${\alpha}$ were observed and confirmed in all given treatments. However, the amount of adipogenesis was found to be statistically significant (p<0.01) with linolenic acid as compared to retinoic acid in combination with TZD's. Conclusion: Retinoic acid was found to produce smaller preadipocytes which have been assumed to have insulin sensitization and hence retinoic acid could be used as a potential agent to sensitize tissues to insulin in combination with TZD's to treat diabetic conditions in humans and animals in future.

• Asian-Australasian Journal of Animal Sciences
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• v.33 no.6
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• pp.1012-1022
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• 2020

Objective: Caseins and fatty acids of milk are synthesized and secreted by the epithelial cells of the mammary gland. All-trans retinoic acid (ATRA), an active metabolite of vitamin A, has been shown to promote mammary development. This study was conducted to determine the effect of ATRA on casein synthesis and fatty acid composition in MAC-T cells. Methods: MAC-T cells were allowed to differentiate for 4 d, treated with ATRA (0, 1.0, 1.5, and 2.0 μM), and incubated for 3 d. We analyzed the fatty acid composition, the mRNA expression of casein and fatty acid synthesis-related genes, and the phosphorylation of casein synthesis-related proteins of MAC-T cells by gas chromatography, quantitative polymerase chain reaction, and western blotting, respectively. Results: In MAC-T cells, ATRA increased the mRNA levels of α_S1-casein and β-casein, janus kinase 2 (JAK2) and E74-like factor 5 of the signal transducer and activator of transcription 5 β (STAT5-β) pathway, ribosomal protein S6 kinase beta-1 (S6K1) and eukaryotic translation initiation factor 4E binding protein 1 of the mammalian target of rapamycin (mTOR) pathway, inhibited the mRNA expression of phosphoinositide 3-kinase and eukaryotic initiation factor 4E of the mTOR pathway, and promoted the phosphorylation of STAT5-β and S6K1 proteins. Additionally, ATRA increased the de novo synthesis of fatty acids, reduced the content of long-chain fatty acids, the ratio of monounsaturated fatty acids to saturated fatty acids (SFA), the ratio of polyunsaturated fatty acids (PUFA) to SFA, and the ratio of ω-6 to ω-3 PUFA. The mRNA levels of acetyl-CoA carboxylase 1, fatty acid synthase, lipoprotein lipase, stearoyl-CoA desaturase, peroxisome proliferator-activated receptor gamma, and sterol regulatory element-binding protein 1 (SREBP1) were enhanced by ATRA. Conclusion: ATRA promotes the synthesis of casein by regulating JAK2/STAT5 pathway and downstream mTOR signaling pathway, and it improves the fatty acid composition of MAC-T cells by regulating SREBP1-related genes.

• Asian-Australasian Journal of Animal Sciences
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• v.13 no.4
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• pp.446-450
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• 2000

The experiment was conducted to study the effects of water soluble vitamins and retinoic acid on the differentiation of preadipocyte from omental, subcutaneous, intermuscular and intramuscular adipose tissue of Hanwoo. Differentiation was assessed by the change in enzyme activity, glycerol-3 phosphate dehydrogenase in serum free cell culture system. Preadipocytes treated with biotin ($10{\mu}M$) and pantothenic acid ($100{\mu}M$) were significantly (p<0.05) less differentiated than those from the control in all adipose tissue depots except intramuscular tissue. Although there was no significance, vitamin C was shown to stimulate the adipocyte conversion in omental and subcutaneous, but not in intermuscular and intramuscular adipose tissues. Lower values of GPDH activity in intermuscular preadipocyte were interpreted to be caused by relatively higher amounts of protein. In this experiment vitamin C did not stimulate fat deposition in intramuscular adipose tissue but further experiments are needed on the role of vitamin C in preadipocyte differentiation. When treated with different levels of retinoic acids, differentiation of preadipocytes was significantly (p<0.05) reduced from the level of $0.5{\mu}g/ml$ in omental and intermuscular, from $50{\mu}g/ml$ in subcutaneous, and in intramuscular at $500{\mu}g/ml$, thus showing that intramuscular preadipocytes were least responsive to retinoic acid in differentiation. All-trans retinoic acid appeared to inhibit the differentiation in a dose dependent manner, regardless of adipose tissues type.

• Nutrition Research and Practice
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• v.3 no.2
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• pp.77-83
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• 2009

Retinoic acids (RAs) modulate growth, differentiation, and apoptosis in normal, pre-malignant & malignant cells. In the present study, the effects of RA isomers (all-trans RA, 13-cis RA, and 9-cis RA) on the cell signal transduction of human breast cancer cells have been studied. The relationship between RAs and an enzymatic antioxidant system was also determined. Estrogen-receptor (ER) positive MCF-7 and ER-negative MDA-MB-231 human breast cancer cells were treated with different doses of each RA isomers, all-trans RA, 13-cis RA, or 9-cis RA. Treatment of RA isomers inhibited cell viability and induced apoptosis of MCF-7 cells as a result of increased caspase activity in cytoplasm and cytochrome C released from mitochondria. All-trans RA was the most effective RA isomer in both cell growth inhibition and induction of apoptosis in MCF-7 cells. However, no significant effect of RA isomers was observed on the cell growth or apoptosis in ER-negative MDA-MB-231 cells. In addition, activities of antioxidant enzymes such as catalase and glutathione peroxidase were decreased effectively after treatment of RA in MCF-7 cells, whereas SOD activity was rarely affected. Thus, the present data suggest that all-trans RA is the most potential inducer of apoptosis and modulator of antioxidant enzymes among RA isomers in MCF-7 human breast cancer cells.

• Journal of Life Science
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• v.8 no.2
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• pp.162-166
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• 1998

The acute myelogeous leukemia cell line, HL-60 is good model to examine leukemia differentiation with nitro blue terazolium reduction assay. We investigated that effect of triterpene acids and ginseng saponin on differentiation of HL-60 cells. Differentiation of HL-60 cells was induced in proportion to ,olar concentration by dibutylyl cAMP, ginseng saponin, lithocholic acid, ginsenoside RH2, and ginsenoside RH3.