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M5939

Sigma-Aldrich

(R)-N4-Hydroxy-N1-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide

>95% (HPLC)

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Synonym(s):
GM6001, Galardin, Ilomastat
Empirical Formula (Hill Notation):
C20H28N4O4
CAS Number:
142880-36-2
Molecular Weight:
388.46
UNSPSC Code:
12352200
PubChem Substance ID:
329818026
NACRES:
NA.77

Quality Level

200

Assay

>95% (HPLC)

form

solid

storage temp.

2-8°C

SMILES string

CNC([C@@H](NC([C@@H](C(C)C)CC(NC)=O)=O)CC1=CNC2=CC=CC=C21)=O

InChI

1S/C20H28N4O3/c1-12(2)15(10-18(25)21-3)19(26)24-17(20(27)22-4)9-13-11-23-16-8-6-5-7-14(13)16/h5-8,11-12,15,17,23H,9-10H2,1-4H3,(H,21,25)(H,22,27)(H,24,26)/t15-,17+/m1/s1

InChI key

PFBWZAGFLVKAGR-WBVHZDCISA-N

Related Categories

Application

(R)-N4-Hydroxy-N1-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide has been used:
  • To study its effect on the profiling of active aggrecanases and their specific aggrecan degradation fragments.
  • To study the involvement of autocrine EGF (epidermal growth factor) receptor activation in the regulation of the morphogenetic process, using human umbilical vein endothelial cells.
  • To study the effect of GM6001 blockade on the expression of angiotensin II, the interstitial collagenases and soluble elastin fragments in explant culture supernatants.

Biochem/physiol Actions

GM6001 promotes cardiovascular and hepatocellular function.
Inhibits a wide variety of matrix metalloproteases with Kis in the nanomolar range. Active in a number of animal models of diseases where matrix metalloproteases are thought to be involved.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The effect of protease inhibitors on the induction of osteoarthritis-related biomarkers in bovine full-depth cartilage explants
He Y, et al.
PLoS ONE, 10(4), e0122700-e0122700 (2015)
D Grobelny et al.
Biochemistry, 31(31), 7152-7154 (1992-08-11)
The hydroxamic acid HONHCOCH2CH(i-Bu)CO-L-Trp-NHMe, isomer 6A (GM 6001), inhibits human skin fibroblast collagenase with Ki of 0.4 nM using the synthetic thiol ester substrate Ac-Pro-Leu-Gly-SCH(i-Bu)CO-Leu-Gly-OEt at pH 6.5. The other isomer, 6B, which has the opposite configuration at the CH2CH(i-Bu)CO
Administration of a matrix metalloproteinase inhibitor after hemorrhage improves cardiovascular and hepatocellular function.
Wang P, et al.
Shock, 6(5), 377-382 (1996)
Autocrine EGF receptor activation mediates endothelial cell migration and vascular morphogenesis induced by VEGF under interstitial flow
Semino CE, et al.
Experimental Cell Research, 312(3), 289-298 (2006)
Evan L Nichols et al.
Cell reports, 30(1), 9-17 (2020-01-09)
Regeneration following spinal root avulsion is broadly unsuccessful despite the regenerative capacity of other PNS-located nerves. By combining focal laser lesioning to model root avulsion in zebrafish, time-lapse imaging, and transgenesis, we identify that regenerating DRG neurons fail to recapitulate
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