Synthesis and biological evaluation of ((4-keto)-phenoxy)methyl biphenyl-4-sulfonamides: A class of potent aggrecanase-1 inhibitors

Hopper, Darrin W.; Vera, Matthew D.; How, David; Sabatini, Joshua; Xiang, Jason; Ipek, Manus; Thomason, Jennifer R.; Hu, Yonghan; Feyfant, Eric; Wang, Qin; Georgiadis, Katy E.; Reifenberg, Erica; Sheldon, Richard; Keohan, Cristin; Majumdar, Manas K.; Morris, Elizabeth A.; Skotnicki, Jerauld S.; Sum, Phaik‐Eng

doi:10.1016/j.bmcl.2009.03.056

Cited by 25 publications

(11 citation statements)

References 10 publications

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“…Kim and Im 2010 compared two subpopulations from human bone marrow, CD105 + , and CD271 + , indicating that the CD271 + subpopulation was slightly more chondrogenic than the CD105 + subpopulation. The chondrogenic differentiation process used to induce differentiation in the subpopulations examined in this study were previously tested to differentiate CD105 + MSCs from synovial membranes by our laboratory [Arufe et al, 2009]; we found that this process did not induce hypertrophy of the cells [Hopper et al, 2009; Jackson et al, 2009]. In the study presented here, we confirmed that no hypertrophy was found in the chondrogenic differentiation of our subpopulations.…”

Section: Discussionsupporting

confidence: 85%

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2011

Developmental Dynamics

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DD ArtPix is a picture gallery of images related to papers published recently in Developmental Dynamics. Most were considered for cover photos, but only one cover photo can be chosen each month. Our authors produce not only excellent science but also excellent art. DD ArtPix provides a sampling of this art for our readers' viewing pleasure. To emphasize their artistic value, images are sometimes manipulated in Photoshop.Images were provided courtesy of authors from the following article: Dev.

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Section: Discussionsupporting

confidence: 85%

DD ArtPix

2011

Developmental Dynamics

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“…Kim and Im 2010 compared two subpopulations from human bone marrow, CD105 + , and CD271 + , indicating that the CD271 + subpopulation was slightly more chondrogenic than the CD105 + subpopulation. The chondrogenic differentiation process used to induce differentiation in the subpopulations examined in this study were previously tested to differentiate CD105 + MSCs from synovial membranes by our laboratory [Arufe et al, 2009]; we found that this process did not induce hypertrophy of the cells [Hopper et al, 2009;Jackson et al, 2009]. In the study presented here, we confirmed that no hypertrophy was found in the chondrogenic differentiation of our subpopulations.…”

Section: Discussionsupporting

confidence: 81%

164 Chondrogenic Potential of Subpopulations of Cells Expressing Mesenchymal Stem Cell Markers Derived From Human Synovial Membranes

Arufe¹,

Fuente²,

Diaz³

et al. 2010

Osteoarthritis and Cartilage

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In this study we analyzed the chondrogenic potential of subpopulations of mesenchymal stem cells (MSCs) derived from human synovial membranes enriched for CD73, CD106, and CD271 markers. Subpopulations of human synovial membrane MSCs enriched for CD73, CD106, and CD271 markers were isolated using a cytometry sorter and characterized by flow cytometry for MSC markers. The expression of Sox9, Nanog, and Runx2 genes by these cells was measured by reverse transcriptase-polymerase chain reaction. The chondrogenesis of each subpopulation was assessed by culturing the cells in a defined medium to produce spontaneous spheroid formation and differentiation towards chondrocyte-like cells. The examination of the spheroids by histological and immunohistochemical analyses for collagen type II (COL2), aggrecan, collagen type I (COL1), metalloprotease 13 (MMP13), and collagen type X (COLX) levels were performed to assess their chondrogenesis capacity. The adipogenesis and osteogenesis potential of each subpopulation was determined using commercial media; the resulting cells were stained with oil red O or red alizarin to test the degree of differentiation. The subpopulations had different profiles of cells positive for the MSC markers CD44, CD69, CD73, CD90, and CD105 and showed different expression levels of the genes Sox9, Nanog, and Runx2 involved in chondrogenesis, undifferentiation, and osteoblastogenesis, respectively. Immunohistochemical analysis demonstrated that COL1, COL2, COLX, MMP13, and aggrecan were expressed in the spheroids as soon as 14 days of culture. The CD271 + subpopulation expressed the highest levels of COL2 staining compared to the other subpopulations. CD105 and Runx2 were shown by immunohistochemistry and genetic analysis to have significantly higher expression CD271 + subpopulation than the other subpopulations. Spheroids formed from CD271-enriched and CD73-enriched MSCs from normal human synovial membranes mimic the native cartilage extracellular matrix more closely than CD106 + MSCs and are possible candidates for use in cartilage tissue engineering. Both cell types have potential for promoting the differentiation of MSCs into chondrocytes, presenting new possibilities for achieving intrinsic cartilage repair. J. Cell. Biochem. 111: 834-845, 2010.

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“…The development of sulfonamides is a fascinating and informative area in medicinal chemistry [ 1 – 3 ]. Its functional group has a long and rich history in organic chemistry and drug discovery [ 4 , 5 ]. The p -toluenesulfonamide and benzenesulfonamides have been widely explored in synthetic chemistry [ 4 , 5 ]; however, few work has been done on the α -tolylsulfonamide.…”

Section: Introductionmentioning

confidence: 99%

Room Temperature Synthesis and Antibacterial Activity of New Sulfonamides Containing N,N-Diethyl-Substituted Amido Moieties

Ajani

Familoni

et al. 2012

International Journal of Medicinal Chemistry

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Sulfonamide drugs which have brought about an antibiotic revolution in medicine are associated with a wide range of biological activities. We have synthesized a series of α-tolylsulfonamide, 1–11 and their substituted N,N-diethyl-2-(phenylmethylsulfonamido) alkanamide derivatives, 12–22 in improved and excellent yields in aqueous medium at room temperature through highly economical synthetic routes. The chemical structures of the synthesized compounds 1–22 were confirmed by analytical and spectral data such as IR, 1H- and 13C-NMR, and mass spectra. The in vitro antibacterial activity of these compounds along with standard clinical reference, streptomycin, was investigated on two key targeted organisms. It was observed that 1-(benzylsulfonyl)pyrrolidine-2-carboxylic acid, 2 emerged as the most active compound against Staphylococcus aureus at MIC value of 1.8 μg/mL while 4-(3-(diethylamino)-3-oxo-2-(phenylmethylsulfonamido) propyl)phenyl phenylmethanesulfonate, 22 was the most active sulfonamide scaffold on Escherichia coli at MIC value of 12.5 μg/mL.

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Synthesis and biological evaluation of ((4-keto)-phenoxy)methyl biphenyl-4-sulfonamides: A class of potent aggrecanase-1 inhibitors

Cited by 25 publications

References 10 publications

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164 Chondrogenic Potential of Subpopulations of Cells Expressing Mesenchymal Stem Cell Markers Derived From Human Synovial Membranes

Room Temperature Synthesis and Antibacterial Activity of New Sulfonamides Containing N,N-Diethyl-Substituted Amido Moieties

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