Synonym
GR 122222X; GR-122222X; GR122222X;
IUPAC/Chemical Name
(S)-2-((S)-2-amino-N-((R)-2-((S)-3-hydroxy-2-((2S,3R)-3-hydroxypyrrolidine-2-carboxamido)propanamido)-3-thioxopropanoyl)propanamido)propanoic 3,5-dihydroxy-2-(mercaptomethyl)-6-methylbenzoic anhydride
InChi Key
NKIYYTUDHBVJTH-UBOLUKANSA-N
InChi Code
InChI=1S/C26H35N5O11S2/c1-10-17(34)6-18(35)13(8-43)19(10)26(41)42-25(40)12(3)31(23(38)11(2)27)24(39)15(9-44)30-21(36)14(7-32)29-22(37)20-16(33)4-5-28-20/h6,9,11-12,14-16,20,28,32-35,43H,4-5,7-8,27H2,1-3H3,(H,29,37)(H,30,36)/t11-,12-,14-,15-,16+,20-/m0/s1
SMILES Code
Cc1c(C(OC([C@@H](N(C([C@@H](NC([C@@H](NC([C@@H]2[C@H](O)CCN2)=O)CO)=O)C=S)=O)C([C@@H](N)C)=O)C)=O)=O)c(CS)c(O)cc1O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
657.71
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Saíz-Urra L, Cabrera Pérez MÁ, Helguera AM, Froeyen M. Combining molecular docking and QSAR studies for modelling the antigyrase activity of cyclothialidine derivatives. Eur J Med Chem. 2011 Jul;46(7):2736-47. doi: 10.1016/j.ejmech.2011.03.061. Epub 2011 Apr 5. PubMed PMID: 21530019.
2: Gevi M, Domenici E. A scintillation proximity assay amenable for screening and characterization of DNA gyrase B subunit inhibitors. Anal Biochem. 2002 Jan 1;300(1):34-9. PubMed PMID: 11743689.
3: Lewis RJ, Singh OM, Smith CV, Skarzynski T, Maxwell A, Wonacott AJ, Wigley DB. The nature of inhibition of DNA gyrase by the coumarins and the cyclothialidines revealed by X-ray crystallography. EMBO J. 1996 Mar 15;15(6):1412-20. PubMed PMID: 8635474; PubMed Central PMCID: PMC450046.
4: Oram M, Dosanjh B, Gormley NA, Smith CV, Fisher LM, Maxwell A, Duncan K. Mode of action of GR122222X, a novel inhibitor of bacterial DNA gyrase. Antimicrob Agents Chemother. 1996 Feb;40(2):473-6. PubMed PMID: 8834902; PubMed Central PMCID: PMC163138.
5: Lewis RJ, Singh OM, Smith CV, Maxwell A, Skarzynski T, Wonacott AJ, Wigley DB. Crystallization of inhibitor complexes of an N-terminal 24 kDa fragment of the DNA gyrase B protein. J Mol Biol. 1994 Aug 5;241(1):128-30. PubMed PMID: 8051702.
