A broad spectrum inhibitor of zinc-containing proteases
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

GM 6001

Item No. 14533

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R)-N4-hydroxy-N1-[(1S)-1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl]-2-(2-methylpropyl)-butanediamide
CAS Number
142880-36-2
Synonyms
  • Galardin
  • Ilomastat
Molecular Formula
C20H28N4O4
Formula Weight
388.5
Purity
≥90%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 0.5 mg/ml
λmax
222, 281 nm
SMILES
O=C(NC)[C@@H](NC([C@@H](CC(NO)=O)CC(C)C)=O)CC1=CNC2=CC=CC=C21
InChi Code
InChI=1S/C20H28N4O4/c1-12(2)8-13(10-18(25)24-28)19(26)23-17(20(27)21-3)9-14-11-22-16-7-5-4-6-15(14)16/h4-7,11-13,17,22,28H,8-10H2,1-3H3,(H,21,27)(H,23,26)(H,24,25)/t13-,17+/m1/s1
InChi Key
NITYDPDXAAFEIT-DYVFJYSZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    500 µg

    $36

    Add

    1 mg

    $68

    Add

    5 mg

    $268

    Add
    Product Description

    GM 6001 is a potent, reversible broad spectrum inhibitor of zinc-containing proteases, including matrix metalloproteinases (MMPs).1 It inhibits zinc-containing thermolysin and elastase from P. aeruginosa, both with Ki values of 20 nM.2 GM 6001 inhibits MMP-1, -2, -7, -8, -9, -12, -13, -14, -16, and -26 with Ki or IC50 values between 0.1 and 10 nM.3,4,5,6 It inhibits disintegrin and metalloproteinase domain-containing (ADAM) proteins ADAM9, ADAM10, ADAM12, and ADAM17 at nanomolar concentrations.7,8 It less potently inhibits lethal factor from B. anthracis anthrax lethal toxin (Ki = 2.74 μM).9 GM 6001 also impairs the growth of the human pathogen Chlamydia by inhibiting peptide deformylase, which contains iron rather than zinc (IC50 = 38 nM).10

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Augé, F., Hornebeck, W., Decarme, M., et al. Improved gelatinase a selectivity by novel zinc binding groups containing galardin derivatives. Bioorg. Med. Chem. Lett. 13(10), 1783-1786 (2003).

    2. Grobelny, D., Poncz, L., and Galardy, R.E. Inhibition of human skin fibroblast collagenase, thermolysin, and Pseudomonas aeruginosa elastase by peptide hydroxamic acids. Biochemistry 31(3), 7152-7154 (1992).

    3. Ma, D., Wu, W., Yang, G., et al. Tetrahydroisoquinoline based sulfonamide hydroxamates as potent matrix metalloproteinase inhibitors. Bioorg. Med. Chem. Lett. 14(1), 47-50 (2004).

    4. Levy, D.E., Lapierre, F., Liang, W., et al. Matrix metalloproteinase inhibitors: A structure-activity study. J. Med. Chem. 41(2), 199-223 (1988).

    5. Fray, M.J., Burslem, M.F., and Dickinson, R.P. Selectivity of inhibition of matrix metalloproteases MMP-3 and MMP-2 by succinyl hydroxamates and their carboxylic acid analogues is dependent on P3' group chirality. Bioorg. Med. Chem. Lett. 11(4), 567-570 (2001).

    6. Yamamoto, M., Tsujishita, H., Hori, N., et al. Inhibition of membrane-type 1 matrix metalloproteinase by hydroxamate inhibitors: An examination of the subsite pocket. J. Med. Chem. 41(8), 1209-1217 (1998).

    7. Oh, M., Im, I., Lee, Y.J., et al. Structure-based virtual screening and biological evaluation of potent and selective ADAM12 inhibitors. Bioorg. Med. Chem. Lett. 14(24), 6071-6074 (2004).

    8. Kwan, J.C., Eksioglu, E.A., Liu, C., et al. Grassystatins A-C from marine cyanobacteria, potent cathepsin E inhibitors that reduce antigen presentation. J. Med. Chem. 52(18), 5732-5747 (2009).

    9. Kocer, S.S., Walker, S.G., Zerler, B., et al. Metalloproteinase inhibitors, nonantimicrobial chemically modified tetracyclines, and ilomastat block Bacillus anthracis lethal factor activity in viable cells. Infect. Immun. 73(11), 7548-7557 (2005).

    10. Balakrishnan, A., Patel, B., Sieber, S.A., et al. Metalloprotease inhibitors GM6001 and TAPI-0 inhibit the obligate intracellular human pathogen Chlamydia trachomatis by targeting peptide deformylase of the bacterium. The Journal of Biological Chemisty 281(24), 16691-26696 (2006).