Fibrostatin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01707 |
| CAS | 91776-42-0 |
| Molecular Weight | 393.41 |
| Molecular Formula | C18H19NO7S |
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Description
Fibrostatin A is a proline hydroxylase inhibitor produced by Strptomyces catenulae.
Specification
| Synonyms | L-Cysteine, N-acetyl-S-((5,8-dihydro-1-hydroxy-3-methoxy-7-methyl-5,8-dioxo-2-naphthalenyl)methyl)- |
| IUPAC Name | (2R)-2-acetamido-3-[(1-hydroxy-3-methoxy-7-methyl-5,8-dioxonaphthalen-2-yl)methylsulfanyl]propanoic acid |
| Canonical SMILES | CC1=CC(=O)C2=CC(=C(C(=C2C1=O)O)CSCC(C(=O)O)NC(=O)C)OC |
| InChI | InChI=1S/C18H19NO7S/c1-8-4-13(21)10-5-14(26-3)11(17(23)15(10)16(8)22)6-27-7-12(18(24)25)19-9(2)20/h4-5,12,23H,6-7H2,1-3H3,(H,19,20)(H,24,25)/t12-/m0/s1 |
| InChI Key | FDDCAZRCTMQKHP-LBPRGKRZSA-N |
Properties
| Melting Point | 186°C |
Reference Reading
1. Unicellular ancestry and mechanisms of diversification of Goodpasture antigen-binding protein
Carl Darris, Fernando Revert, Francisco Revert-Ros, Roberto Gozalbo-Rovira, Andrew Feigley, Aaron Fidler, Ernesto Lopez-Pascual, Juan Saus, Billy G Hudson J Biol Chem. 2019 Jan 18;294(3):759-769. doi: 10.1074/jbc.RA118.006225. Epub 2018 Oct 30.
The emergence of the basement membrane (BM), a specialized form of extracellular matrix, was essential in the unicellular transition to multicellularity. However, the mechanism is unknown. Goodpasture antigen-binding protein (GPBP), a BM protein, was uniquely poised to play diverse roles in this transition owing to its multiple isoforms (GPBP-1, -2, and -3) with varied intracellular and extracellular functions (ceramide trafficker and protein kinase). We sought to determine the evolutionary origin of GPBP isoforms. Our findings reveal the presence of GPBP in unicellular protists, with GPBP-2 as the most ancient isoform. In vertebrates, GPBP-1 assumed extracellular function that is further enhanced by membrane-bound GPBP-3 in mammalians, whereas GPBP-2 retained intracellular function. Moreover, GPBP-2 possesses a dual intracellular/extracellular function in cnidarians, an early nonbilaterian group. We conclude that GPBP functioning both inside and outside the cell was of fundamental importance for the evolutionary transition to animal multicellularity and tissue evolution.
2. Embryo implantation triggers dynamic spatiotemporal expression of the basement membrane toolkit during uterine reprogramming
Celestial R Jones-Paris, Sayan Paria, Taloa Berg, Juan Saus, Gautam Bhave, Bibhash C Paria, Billy G Hudson Matrix Biol. 2017 Jan;57-58:347-365. doi: 10.1016/j.matbio.2016.09.005. Epub 2016 Sep 10.
Basement membranes (BMs) are specialized extracellular scaffolds that influence behaviors of cells in epithelial, endothelial, muscle, nervous, and fat tissues. Throughout development and in response to injury or disease, BMs are fine-tuned with specific protein compositions, ultrastructure, and localization. These features are modulated through implements of the BM toolkit that is comprised of collagen IV, laminin, perlecan, and nidogen. Two additional proteins, peroxidasin and Goodpasture antigen-binding protein (GPBP), have recently emerged as potential members of the toolkit. In the present study, we sought to determine whether peroxidasin and GPBP undergo dynamic regulation in the assembly of uterine tissue BMs in early pregnancy as a tractable model for dynamic adult BMs. We explored these proteins in the context of collagen IV and laminin that are known to extensively change for decidualization. Electron microscopic analyses revealed: 1) a smooth continuous layer of BM in between the epithelial and stromal layers of the preimplantation endometrium; and 2) interrupted, uneven, and progressively thickened BM within the pericellular space of the postimplantation decidua. Quantification of mRNA levels by qPCR showed changes in expression levels that were complemented by immunofluorescence localization of peroxidasin, GPBP, collagen IV, and laminin. Novel BM-associated and subcellular spatiotemporal localization patterns of the four components suggest both collective pericellular functions and distinct functions in the uterus during reprogramming for embryo implantation.
3. Selective targeting of collagen IV in the cancer cell microenvironment reduces tumor burden
Fernando Revert, Francisco Revert-Ros, Raül Blasco, et al. Oncotarget. 2018 Jan 19;9(13):11020-11045. doi: 10.18632/oncotarget.24280. eCollection 2018 Feb 16.
Goodpasture antigen-binding protein (GPBP) is an exportable1 Ser/Thr kinase that induces collagen IV expansion and has been associated with chemoresistance following epithelial-to-mesenchymal transition (EMT). Here we demonstrate that cancer EMT phenotypes secrete GPBP (mesenchymal GPBP) which displays a predominant multimeric oligomerization and directs the formation of previously unrecognized mesh collagen IV networks (mesenchymal collagen IV). Yeast two-hybrid (YTH) system was used to identify a 260SHCIE264 motif critical for multimeric GPBP assembly which then facilitated design of a series of potential peptidomimetics. The compound 3-[4''-methoxy-3,2'-dimethyl-(1,1';4',1'')terphenyl-2''-yl]propionic acid, or T12, specifically targets mesenchymal GPBP and disturbs its multimerization without affecting kinase catalytic site. Importantly, T12 reduces growth and metastases of tumors populated by EMT phenotypes. Moreover, low-dose doxorubicin sensitizes epithelial cancer precursor cells to T12, thereby further reducing tumor load. Given that T12 targets the pathogenic mesenchymal GPBP, it does not bind significantly to normal tissues and therapeutic dosing was not associated with toxicity. T12 is a first-in-class drug candidate to treat cancer by selectively targeting the collagen IV of the tumor cell microenvironment.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
