Synonym
AN-0128; CRM-0005; ONT-0001; AN0128; CRM0005; ONT0001; AN 0128; CRM 0005; ONT 0001
IUPAC/Chemical Name
((bis(3-chloro-4-methylphenyl)boraneyl)oxy)(3-hydroxypyridin-2-yl)methanone
InChi Key
ZTLSOLUCMQEGEA-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H16BCl2NO3/c1-12-5-7-14(10-16(12)22)21(15-8-6-13(2)17(23)11-15)27-20(26)19-18(25)4-3-9-24-19/h3-11,25H,1-2H3
SMILES Code
CC1=CC=C(B(OC(C2=NC=CC=C2O)=O)C3=CC=C(C)C(Cl)=C3)C=C1Cl
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
Biological target:
AN0128 is a boron-containing antibacterial and anti-inflammatory agent against S. aureus, S. epidermidis, P. acnes, B. subtilis with minimum inhibitory concentration (MIC) values of 1, 0.5, 0.3, 1 μg/mL.
In vitro activity:
In order to test for concomitant anti-inflammatory activity, 3-hydroxypyridine-2-carbonyloxy-bis(3-chloro-4-methylphenyl)borane (AN0128) was evaluated for its ability to inhibit release of inflammatory cytokines from human peripheral blood mononuclear cells (PBMCs). Either lipopolysaccharide (LPS, 1 μg/mL), Concanavalin A (1 μg/mL) or phyto-hemagglutinin (PHA, 2 μg/mL) was used to induce the release of cytokines from the PBMCs. AN0128 showed strong inhibition of the release of pro-inflammatory cytokines but no inhibition of IFN-γ or IL-4 release. From these studies, AN0128 was shown to have the best combination of anti-bacterial and anti-inflammatory activities.
Reference: Bioorg Med Chem Lett. 2006 Dec 1;16(23):5963-7. https://pubmed.ncbi.nlm.nih.gov/16997550/
In vivo activity:
To test AN0128’s potential effectiveness in treating periodontal disease, experimental periodontitis was induced in the rat by placing ligatures and assessed the impact of AN0128 and positive and negative controls by micro-CT and histologic measurements. Daily application of AN0128 (1%) compared with controls reduced bone loss by 38 to 44% (P < 0.05), while vehicle alone had no effect (P > 0.05). The reduction in bone loss with AN0128 was similar to that achieved with a NSAID, ketorolac, and Total toothpaste containing triclosan. AN0128 also reduced the level of gingival inflammation 42% compared with the ligature only (P < 0.05), whereas vehicle alone had no effect (P > 0.05). The results indicate that AN0128 significantly reduces the formation of an inflammatory infiltrate and reduces bone loss, measured histologically and by micro-CT.
Reference: J Dent Res. 2008 Feb;87(2):148-52. https://pubmed.ncbi.nlm.nih.gov/18218841/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
125.0 |
312.45 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
400.06
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. Baker SJ, Akama T, Zhang YK, Sauro V, Pandit C, Singh R, Kully M, Khan J, Plattner JJ, Benkovic SJ, Lee V, Maples KR. Identification of a novel boron-containing antibacterial agent (AN0128) with anti-inflammatory activity, for the potential treatment of cutaneous diseases. Bioorg Med Chem Lett. 2006 Dec 1;16(23):5963-7. doi: 10.1016/j.bmcl.2006.08.130. Epub 2006 Sep 25. PMID: 16997550.
2. Luan Q, Desta T, Chehab L, Sanders VJ, Plattner J, Graves DT. Inhibition of experimental periodontitis by a topical boron-based antimicrobial. J Dent Res. 2008 Feb;87(2):148-52. doi: 10.1177/154405910808700208. PMID: 18218841.
In vitro protocol:
1. Baker SJ, Akama T, Zhang YK, Sauro V, Pandit C, Singh R, Kully M, Khan J, Plattner JJ, Benkovic SJ, Lee V, Maples KR. Identification of a novel boron-containing antibacterial agent (AN0128) with anti-inflammatory activity, for the potential treatment of cutaneous diseases. Bioorg Med Chem Lett. 2006 Dec 1;16(23):5963-7. doi: 10.1016/j.bmcl.2006.08.130. Epub 2006 Sep 25. PMID: 16997550.
In vivo protocol:
1. Luan Q, Desta T, Chehab L, Sanders VJ, Plattner J, Graves DT. Inhibition of experimental periodontitis by a topical boron-based antimicrobial. J Dent Res. 2008 Feb;87(2):148-52. doi: 10.1177/154405910808700208. PMID: 18218841.
1: Baker SJ, Akama T, Zhang YK, Sauro V, Pandit C, Singh R, Kully M, Khan J, Plattner JJ, Benkovic SJ, Lee V, Maples KR. Identification of a novel boron-containing antibacterial agent (AN0128) with anti-inflammatory activity, for the potential treatment of cutaneous diseases. Bioorg Med Chem Lett. 2006 Dec 1;16(23):5963-7. PubMed PMID: 16997550.
2: Luan Q, Desta T, Chehab L, Sanders VJ, Plattner J, Graves DT. Inhibition of experimental periodontitis by a topical boron-based antimicrobial. J Dent Res. 2008 Feb;87(2):148-52. PubMed PMID: 18218841.
3: Ciaravino V, Plattner J, Chanda S. An assessment of the genetic toxicology of novel boron-containing therapeutic agents. Environ Mol Mutagen. 2013 Jun;54(5):338-46. doi: 10.1002/em.21779. PubMed PMID: 23625818.
