Synonym
BB-78485; BB78485; BB 78485.
IUPAC/Chemical Name
(2R)-N-hydroxy-3-naphthalen-2-yl-2-(naphthalen-2-ylsulfonylamino)propanamide
InChi Key
MMOUXLMPQFMDRD-JOCHJYFZSA-N
InChi Code
InChI=1S/C23H20N2O4S/c26-23(24-27)22(14-16-9-10-17-5-1-3-7-19(17)13-16)25-30(28,29)21-12-11-18-6-2-4-8-20(18)15-21/h1-13,15,22,25,27H,14H2,(H,24,26)/t22-/m1/s1
SMILES Code
O=C(NO)[C@H](NS(=O)(C1=CC=C2C=CC=CC2=C1)=O)CC3=CC=C4C=CC=CC4=C3
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
More Info
UDP-3-O-(R-3-hydroxymyristol)-N-acetylglucosamine deacetylase (LpxC) is a cytosolic zinc-based deacetylase that catalyzes the first committed step in the biosynthesis of lipid A, which is essential for the survival of Gram-negative bacteria.
Biological target:
BB-78485 is a LpxC inhibitor.
In vitro activity:
BB-78485 is highly effective in suppressing the activity of Escherichia coli LpxC (EcLpxC) but not divergent orthologs such as Pseudomonas aeruginosa LpxC (PaLpxC) in vitro.
Reference: ACS Chem Biol. 2014 Jan 17;9(1):237-46. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3947053/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
420.48
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 |
Formulation protocol:
1. Lee CJ, Liang X, Gopalaswamy R, Najeeb J, Ark ED, Toone EJ, Zhou P. Structural basis of the promiscuous inhibitor susceptibility of Escherichia coli LpxC. ACS Chem Biol. 2014 Jan 17;9(1):237-46. doi: 10.1021/cb400067g. Epub 2013 Oct 31. PMID: 24117400; PMCID: PMC3947053.
In vitro protocol:
1. Lee CJ, Liang X, Gopalaswamy R, Najeeb J, Ark ED, Toone EJ, Zhou P. Structural basis of the promiscuous inhibitor susceptibility of Escherichia coli LpxC. ACS Chem Biol. 2014 Jan 17;9(1):237-46. doi: 10.1021/cb400067g. Epub 2013 Oct 31. PMID: 24117400; PMCID: PMC3947053.
1: Kalinin DV, Holl R. Insights into the Zinc-Dependent Deacetylase LpxC: Biochemical Properties and Inhibitor Design. Curr Top Med Chem. 2016;16(21):2379-430. Review. PubMed PMID: 27072691.
2: Lee CJ, Liang X, Gopalaswamy R, Najeeb J, Ark ED, Toone EJ, Zhou P. Structural basis of the promiscuous inhibitor susceptibility of Escherichia coli LpxC. ACS Chem Biol. 2014 Jan 17;9(1):237-46. doi: 10.1021/cb400067g. Epub 2013 Oct 31. PubMed PMID: 24117400; PubMed Central PMCID: PMC3947053.
3: Pradhan D, Priyadarshini V, Munikumar M, Swargam S, Umamaheswari A, Bitla A. Para-(benzoyl)-phenylalanine as a potential inhibitor against LpxC of Leptospira spp.: homology modeling, docking, and molecular dynamics study. J Biomol Struct Dyn. 2014;32(2):171-85. doi: 10.1080/07391102.2012.758056. Epub 2013 Feb 5. PubMed PMID: 23383626.
4: Mochalkin I, Knafels JD, Lightle S. Crystal structure of LpxC from Pseudomonas aeruginosa complexed with the potent BB-78485 inhibitor. Protein Sci. 2008 Mar;17(3):450-7. doi: 10.1110/ps.073324108. PubMed PMID: 18287278; PubMed Central PMCID: PMC2248309.
5: Clements JM, Coignard F, Johnson I, Chandler S, Palan S, Waller A, Wijkmans J, Hunter MG. Antibacterial activities and characterization of novel inhibitors of LpxC. Antimicrob Agents Chemother. 2002 Jun;46(6):1793-9. PubMed PMID: 12019092; PubMed Central PMCID: PMC127247.
