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Article ; Online: Stabilization of Naphthalene Diimide Anions by Ion Pair Formation in Nonaqueous Organic Redox Flow Batteries.

Ahn, Seongmo / Son, Mina / Singh, Vikram / Yun, Ariyeong / Baik, Mu-Hyun / Byon, Hye Ryung

Journal of the American Chemical Society

2024 Volume 146, Issue 7, Page(s) 4521–4531

Abstract: In redox flow batteries, a compelling strategy for enhancing the charge capacity of redox-active organic molecules involves storing multiple electrons within a single molecule. However, this approach poses unique challenges such as chemical instability ... ...

Abstract	In redox flow batteries, a compelling strategy for enhancing the charge capacity of redox-active organic molecules involves storing multiple electrons within a single molecule. However, this approach poses unique challenges such as chemical instability by forming radicals, elevated energy requirements, and unsustainable charge concentration. Ion pairing is a possible solution to achieve charge neutrality and engineer redox potential shifts but has received limited attention. In this study, we demonstrate that Li
Language	English
Publishing date	2024-02-12
Publishing country	United States
Document type	Journal Article
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021/jacs.3c11176
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Article ; Online: Construction of Seven-Membered Oxacycles Using a Rh(I)-Catalyzed Cascade C-C Formation/Cleavage of Cyclobutenol Derivatives.

Ham, Jin Su / Son, Mina / Na, Christina G / Park, Bohyun / Baik, Mu-Hyun / Sarpong, Richmond

The Journal of organic chemistry

2024 Volume 89, Issue 7, Page(s) 4647–4656

Abstract: Herein, we describe the synthesis of substituted oxepane derivatives through the skeletal remodeling of 4-hydroxy-2-cyclobutenones, which are readily prepared from commercially available dialkyl squarates upon their reaction with acrylonitrile. ... ...

Abstract	Herein, we describe the synthesis of substituted oxepane derivatives through the skeletal remodeling of 4-hydroxy-2-cyclobutenones, which are readily prepared from commercially available dialkyl squarates upon their reaction with acrylonitrile. Mechanistically, a Rh(I)-catalyzed C-C bond formation and cleavage cascade is proposed. Specifically, a fused [3.2.0] bicycle is proposed to form from dialkyl squarate-derived cyclobutenols via an unusual Rh(I)-catalyzed intermolecular oxa-Michael addition of a tertiary alcohol with acrylonitrile, followed by an intramolecular conjugate addition/migratory insertion. Subsequent C(sp
Language	English
Publishing date	2024-03-18
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.3c02914
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Article: Allene C(sp²)–H Activation and Alkenylation Catalyzed by Palladium

Schreib, Benedikt S. / Son, Mina / Aouane, Françoise A. / Baik, Mu-Hyun / Carreira, Erick M.

Journal of the American Chemical Society. 2021 Dec. 16, v. 143, no. 51

2021

Abstract: The selective transition-metal-mediated activation of C(sp²)–H bonds of allenes is a formidable challenge because of the competitive, intrinsic reactivity of cumulated double bonds. Herein, we report a Pd-catalyzed C–H alkenylation of electronically ... ...

Abstract	The selective transition-metal-mediated activation of C(sp²)–H bonds of allenes is a formidable challenge because of the competitive, intrinsic reactivity of cumulated double bonds. Herein, we report a Pd-catalyzed C–H alkenylation of electronically unbiased allenes, affording penta-1,2,4-triene products in up to 94% yield. A picolinamide directing group enables the formation of putative allenyl-palladacycles, which subsequently participate in a turnover-limiting Heck-type reaction with electron-deficient alkene coupling partners. This mechanistic proposal is consistent with experimental and computational investigations. Additionally, we report for the first time the use of picolinamide N,O-acetals as readily removable auxiliaries for C–H activation reactions, allowing the efficient alkenylation of allenyl carbinol derivatives. Successful removal of the directing groups without affecting the reactive penta-1,2,4-triene substructure of the products is demonstrated.
Keywords	allene ; carbon-hydrogen bond activation ; palladium
Language	English
Dates of publication	2021-1216
Size	p. 21705-21712.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021/jacs.1c11528
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Article ; Online: Allene C(sp

Schreib, Benedikt S / Son, Mina / Aouane, Françoise A / Baik, Mu-Hyun / Carreira, Erick M

Journal of the American Chemical Society

2021 Volume 143, Issue 51, Page(s) 21705–21712

Abstract: The selective transition-metal-mediated activation of C( ... ...

Abstract	The selective transition-metal-mediated activation of C(sp
Language	English
Publishing date	2021-12-16
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021/jacs.1c11528
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Article: Spin-state crossover in photo-catalyzed nitrile dihydroboration

Elsby, Matthew R / Oh, Changjin / Son, Mina / Kim, Scott Y H / Baik, Mu-Hyun / Baker, R Tom

Chemical science

2022 Volume 13, Issue 42, Page(s) 12550–12559

Abstract: The role of S-donors in ligand-assisted catalysis using first-row metals has not been broadly investigated. Herein is described a combined experimental and computational mechanistic study of the dihydroboration of nitriles with pinacolborane (HBpin) ... ...

Abstract	The role of S-donors in ligand-assisted catalysis using first-row metals has not been broadly investigated. Herein is described a combined experimental and computational mechanistic study of the dihydroboration of nitriles with pinacolborane (HBpin) catalyzed by the Mn(i) complex, Mn(κ
Language	English
Publishing date	2022-10-20
Publishing country	England
Document type	Journal Article
ZDB-ID	2559110-1
ISSN	2041-6539 ; 2041-6520
ISSN (online)	2041-6539
ISSN	2041-6520
DOI	10.1039/d2sc04339d
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Article ; Online: 4-Methoxyphenyl (E)-3-(Furan-3-yl) Acrylate Inhibits Vascular Smooth Muscle Cell Proliferation.

Han, Seongho / Son, Mina / Lee, Yunmi / Cheon, Sae Hee / Kim, Sung-Whan

Journal of cardiovascular pharmacology

2020 Volume 76, Issue 1, Page(s) 106–111

Abstract: The Cordyceps extract exhibits antiproliferative potential in vascular smooth muscle cells (SMCs) through the mitogen-activated protein kinase signaling pathway. In this study, we aimed to identify the active compounds in the Cordyceps extract and ... ...

Abstract	The Cordyceps extract exhibits antiproliferative potential in vascular smooth muscle cells (SMCs) through the mitogen-activated protein kinase signaling pathway. In this study, we aimed to identify the active compounds in the Cordyceps extract and analyze their role in remodeling the arterial wall. On investigation, we discovered the following active compound: 4-methoxyphenyl (E)-3-(furan-3-yl) acrylate and synthesized it. We performed antiproliferation and antimigration assays in addition to an in vivo vessel wall remodeling experiment. Investigation of the mechanism adopted by the active compound to remodel the vessel was performed. The newly synthesized compound inhibited the proliferation and migration of SMCs. Treatment with the synthesized compound reduced neointima formation in the balloon-injured Sprague-Dawley rat model. In addition, this compound inhibited the activation of matrix metalloproteinase-2 and matrix metalloproteinase-9 in type I collagen-activated SMCs. Moreover, this compound suppressed the expression of cycloxygenase-2 (COX-2) in SMCs. Therefore, this compound can exert potential antiarteriosclerotic effects by modulating vessel wall remodeling. In conclusion, the newly synthesized 4-methoxyphenyl (E)-3-(furan-3-yl) acrylate might be an alternative therapeutic intervention for the treatment of atherosclerosis.
MeSH term(s)	Animals ; Carotid Artery Injuries/metabolism ; Carotid Artery Injuries/pathology ; Carotid Artery Injuries/prevention & control ; Cell Movement/drug effects ; Cell Proliferation/drug effects ; Cells, Cultured ; Cordyceps/chemistry ; Cyclooxygenase 2/metabolism ; Disease Models, Animal ; Furans/chemical synthesis ; Furans/isolation & purification ; Furans/pharmacology ; Male ; Matrix Metalloproteinase 2/metabolism ; Matrix Metalloproteinase 9/metabolism ; Muscle, Smooth, Vascular/drug effects ; Muscle, Smooth, Vascular/metabolism ; Muscle, Smooth, Vascular/pathology ; Myocytes, Smooth Muscle/drug effects ; Myocytes, Smooth Muscle/metabolism ; Myocytes, Smooth Muscle/pathology ; Neointima ; Rats, Sprague-Dawley ; Vascular Remodeling/drug effects
Chemical Substances	Furans ; Cyclooxygenase 2 (EC 1.14.99.1) ; Ptgs2 protein, rat (EC 1.14.99.1) ; Matrix Metalloproteinase 2 (EC 3.4.24.24) ; Mmp2 protein, rat (EC 3.4.24.24) ; Matrix Metalloproteinase 9 (EC 3.4.24.35) ; Mmp9 protein, rat (EC 3.4.24.35)
Language	English
Publishing date	2020-07-09
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	391970-5
ISSN	1533-4023 ; 0160-2446
ISSN (online)	1533-4023
ISSN	0160-2446
DOI	10.1097/FJC.0000000000000831
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Article ; Online: Angiogenic characteristics of human stromal vascular fraction in ischemic hindlimb.

Jin, Enze / Chae, Dong-Sik / Son, Mina / Kim, Sung-Whan

International journal of cardiology

2017 Volume 234, Page(s) 38–47

Abstract: Introduction: In this study, we sought to characterize the angio-vasculogenic property of human adipose tissue-derived stromal vascular fraction (SVF) and to determine the therapeutic potential of SVF in the context of experimental ischemia. Although ... ...

Abstract	Introduction: In this study, we sought to characterize the angio-vasculogenic property of human adipose tissue-derived stromal vascular fraction (SVF) and to determine the therapeutic potential of SVF in the context of experimental ischemia. Although human SVF is used for cell therapy, its angiogenic and vasculogenic characteristics have not been fully elucidated. Methods and results: We conducted flow cytometry, microarray, quantitative (q)-PCR, Matrigel tube formation assays and in vivo therapeutic assays using an ischemic hind limb mouse model. Gene/micro RNA microarray, quantitative (q)-PCR results revealed that the representative pro-angiogenic factors were highly upregulated in SVF compared with human adipose-derived mesenchymal stem cells (ASCs). In addition, SVF exhibited high expression of endothelium-specific genes and showed robust in vitro micro-vascular formation. SVF was transplanted into ischemic mouse hind limbs and compared with ASC transplantation. SVF transplantation prevented limb loss and augmented blood perfusion, indicating that SVF promotes neovascularization in hind limb ischemia. Transplanted SVF showed high vasculogenic potential in vivo compared with transplanted ASCs. Conclusions: Our data indicate that SVF has remarkable therapeutic effects on hind limb ischemia via robust angiogenic and vasculogenic activity.
Language	English
Publishing date	2017-05-01
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	779519-1
ISSN	1874-1754 ; 0167-5273
ISSN (online)	1874-1754
ISSN	0167-5273
DOI	10.1016/j.ijcard.2017.02.080
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Article ; Online: Stromal vascular fraction shows robust wound healing through high chemotactic and epithelialization property.

Chae, Dong-Sic / Han, Seongho / Son, Mina / Kim, Sung-Whan

Cytotherapy

2017 Volume 19, Issue 4, Page(s) 543–554

Abstract: Background: Although human stromal vascular fraction (SVF) has been regarded as an attractive stem cell source, its therapeutic mechanism in wound healing has not been fully elucidated.: Aims: In this study, we investigated the molecular ... ...

Abstract	Background: Although human stromal vascular fraction (SVF) has been regarded as an attractive stem cell source, its therapeutic mechanism in wound healing has not been fully elucidated. Aims: In this study, we investigated the molecular characteristics and therapeutic property of SVF for wound healing. Methods: Microarray data showed that SVF cells are enriched with a higher level of wound healing or epithelium development-related genes and micro RNA. Results: Quantitative polymerase chain reaction (PCR) and reverse transcriptase PCR results revealed that the epithelialization growth factor, epidermal growth factor (EGF), chemokines, stromal cell-derived factor (SDF-1 or CXCL12), neutrophil-activating protein-2 (NAP-2 or CXCL7), chemokine receptors (CXCR1, CCR2 and CCR3) and wound healing genes were up-regulated in SVF compared with those in adipose-derived mesenchymal stem cells (ASCs). An in vitro scratch wound closure experiment demonstrated that co-culture with SVF substantially accelerated the wound closure of fibroblasts. Wounds in nude mice were created by skin excisions followed by injections of SVF with Pluronic hydrogel. SVF implantation highly accelerated wound closure and increased cellularity and re-epithelialization. In addition, the transplanted SVF exhibited high engraftment rates in the wound area, suggesting direct benefits for cutaneous closure. Conclusions: Taken together, these data suggest that SVF possesses high therapeutic capability for wound healing via the secretion of epithelialization and chemotactic growth factors and enhanced engraftment properties.
MeSH term(s)	Animals ; Blood Vessels/cytology ; Cells, Cultured ; Chemotaxis ; Coculture Techniques ; Fibroblasts/cytology ; Fibroblasts/physiology ; Gene Expression Regulation ; Human Umbilical Vein Endothelial Cells ; Humans ; Intercellular Signaling Peptides and Proteins/genetics ; Male ; Mesenchymal Stromal Cells/cytology ; Mice ; Mice, Nude ; Re-Epithelialization/genetics ; Re-Epithelialization/physiology ; Stromal Cells/cytology ; Stromal Cells/physiology ; Stromal Cells/transplantation ; Up-Regulation
Chemical Substances	Intercellular Signaling Peptides and Proteins
Language	English
Publishing date	2017-04
Publishing country	England
Document type	Journal Article
ZDB-ID	2039821-9
ISSN	1477-2566 ; 1465-3249
ISSN (online)	1477-2566
ISSN	1465-3249
DOI	10.1016/j.jcyt.2017.01.006
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Zs.A 5601: Show issues

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Article ; Online: The Protective Effect of Zebularine, an Inhibitor of DNA Methyltransferase, on Renal Tubulointerstitial Inflammation and Fibrosis.

Koh, Eun Sil / Kim, Soojeong / Son, Mina / Park, Ji-Young / Pyo, Jaehyuk / Kim, Wan-Young / Kim, Minyoung / Chung, Sungjin / Park, Cheol Whee / Kim, Ho-Shik / Shin, Seok Joon

International journal of molecular sciences

2022 Volume 23, Issue 22

Abstract: Renal fibrosis, the final pathway of chronic kidney disease, is caused by genetic and epigenetic mechanisms. Although DNA methylation has drawn attention as a developing mechanism of renal fibrosis, its contribution to renal fibrosis has not been ... ...

Abstract	Renal fibrosis, the final pathway of chronic kidney disease, is caused by genetic and epigenetic mechanisms. Although DNA methylation has drawn attention as a developing mechanism of renal fibrosis, its contribution to renal fibrosis has not been clarified. To address this issue, the effect of zebularine, a DNA methyltransferase inhibitor, on renal inflammation and fibrosis in the murine unilateral ureteral obstruction (UUO) model was analyzed. Zebularine significantly attenuated renal tubulointerstitial fibrosis and inflammation. Zebularine decreased trichrome, α-smooth muscle actin, collagen IV, and transforming growth factor-β1 staining by 56.2%. 21.3%, 30.3%, and 29.9%, respectively, at 3 days, and by 54.6%, 41.9%, 45.9%, and 61.7%, respectively, at 7 days after UUO. Zebularine downregulated mRNA expression levels of matrix metalloproteinase (MMP)-2, MMP-9, fibronectin, and Snail1 by 48.6%. 71.4%, 31.8%, and 42.4%, respectively, at 7 days after UUO. Zebularine also suppressed the activation of nuclear factor-κB (NF-κB) and the expression of pro-inflammatory cytokines, including tumor necrosis factor-α, interleukin (IL)-1β, and IL-6, by 69.8%, 74.9%, and 69.6%, respectively, in obstructed kidneys. Furthermore, inhibiting DNA methyltransferase buttressed the nuclear expression of nuclear factor (erythroid-derived 2)-like factor 2, which upregulated downstream effectors such as catalase (1.838-fold increase at 7 days, p < 0.01), superoxide dismutase 1 (1.494-fold increase at 7 days, p < 0.05), and NAD(P)H: quinone oxidoreduate-1 (1.376-fold increase at 7 days, p < 0.05) in obstructed kidneys. Collectively, these findings suggest that inhibiting DNA methylation restores the disrupted balance between pro-inflammatory and anti-inflammatory pathways to alleviate renal inflammation and fibrosis. Therefore, these results highlight the possibility of DNA methyltransferases as therapeutic targets for treating renal inflammation and fibrosis.
MeSH term(s)	Mice ; Animals ; Fibrosis ; Nephritis/pathology ; Ureteral Obstruction/complications ; Ureteral Obstruction/drug therapy ; Ureteral Obstruction/genetics ; Inflammation/pathology ; Renal Insufficiency, Chronic/complications ; DNA Modification Methylases ; DNA/therapeutic use
Chemical Substances	pyrimidin-2-one beta-ribofuranoside (7A9Y5SX0GY) ; DNA Modification Methylases (EC 2.1.1.-) ; DNA (9007-49-2)
Language	English
Publishing date	2022-11-14
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2019364-6
ISSN	1422-0067 ; 1422-0067 ; 1661-6596
ISSN (online)	1422-0067
ISSN	1422-0067 ; 1661-6596
DOI	10.3390/ijms232214045
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Article ; Online: C-H/C-C Functionalization Approach to N-Fused Heterocycles from Saturated Azacycles.

Ham, Jin Su / Park, Bohyun / Son, Mina / Roque, Jose B / Jurczyk, Justin / Yeung, Charles S / Baik, Mu-Hyun / Sarpong, Richmond

Journal of the American Chemical Society

2020 Volume 142, Issue 30, Page(s) 13041–13050

Abstract: Herein we report the synthesis of substituted indolizidines and related N-fused bicycles from simple saturated cyclic amines through sequential C-H and C-C bond functionalizations. Inspired by the Norrish-Yang Type II reaction, C-H functionalization of ... ...

Abstract	Herein we report the synthesis of substituted indolizidines and related N-fused bicycles from simple saturated cyclic amines through sequential C-H and C-C bond functionalizations. Inspired by the Norrish-Yang Type II reaction, C-H functionalization of azacycles is achieved by forming α-hydroxy-β-lactams from precursor α-ketoamide derivatives under mild, visible light conditions. Selective cleavage of the distal C(sp
MeSH term(s)	Aza Compounds/chemistry ; Cyclization ; Heterocyclic Compounds/chemical synthesis ; Heterocyclic Compounds/chemistry ; Indolizidines/chemical synthesis ; Indolizidines/chemistry ; Molecular Structure ; Stereoisomerism
Chemical Substances	Aza Compounds ; Heterocyclic Compounds ; Indolizidines
Language	English
Publishing date	2020-07-19
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021/jacs.0c04278
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