Synonym
(S)-Homoserine lactone;
IUPAC/Chemical Name
(S)-3-aminodihydrofuran-2(3H)-one hydrochloride
InChi Key
XBKCXPRYTLOQKS-DFWYDOINSA-N
InChi Code
InChI=1S/C4H7NO2.ClH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/m0./s1
SMILES Code
O=C1[C@H](CCO1)N.Cl
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
>3 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:
L-Homoserine lactone is a synthetic intermediate.
In vitro activity:
3-O-C12-HSL increased the expression level of the lncRNA NRIR, impeding monocyte-derived dendritic cell (Mo-DC) maturation. These results indicate that 3-O-C12-HSL indeed affects the differentiation and maturation of Mo-DCs through NRIR.
Reference: J Biosci. 2021;46:65. https://pubmed.ncbi.nlm.nih.gov/34219741/
In vivo activity:
Further testing of N-3-oxo-dodecanoyl-L-homoserine lactone, the most potent inhibitor and a product of Pseudomonas aeruginosa, revealed that it also attenuated chemotaxis and LPS induced cytokine production. In vivo, N-3-oxo-dodecanoyl-L-homoserine lactone inhibited the passive cutaneous anaphylaxis response in mice.
Reference: Inflamm Res. 2017 Mar;66(3):259-268. https://pubmed.ncbi.nlm.nih.gov/27896412/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
10.0 |
72.69 |
| PBS (pH 7.2) |
10.0 |
72.69 |
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
137.56
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. Zhang X, Liu Y, Lu Y, Li S, Liu J, Zhang Y, Wang L, Li MO, Luo Y, Zhang W, Chen C, Li Y. N-3-(oxododecanoyl)-L-homoserine lactone suppresses dendritic cell maturation by upregulating the long noncoding RNA NRIR. J Biosci. 2021;46:65. PMID: 34219741.
2. Yadav VK, Singh PK, Sharma D, Pandey H, Singh SK, Agarwal V. Autoinducer N-(3-oxododecanoyl)-l-homoserine lactone induces calcium and reactive oxygen species-mediated mitochondrial damage and apoptosis in blood platelets. Microb Pathog. 2021 May;154:104792. doi: 10.1016/j.micpath.2021.104792. Epub 2021 Feb 23. PMID: 33636321.
3. Khambati I, Han S, Pijnenburg D, Jang H, Forsythe P. The bacterial quorum-sensing molecule, N-3-oxo-dodecanoyl-L-homoserine lactone, inhibits mediator release and chemotaxis of murine mast cells. Inflamm Res. 2017 Mar;66(3):259-268. doi: 10.1007/s00011-016-1013-3. Epub 2016 Nov 28. PMID: 27896412.
4. Golpasha ID, Mousavi SF, Owlia P, Siadat SD, Irani S. Immunization with 3-oxododecanoyl-L-homoserine lactone-r-PcrV conjugate enhances survival of mice against lethal burn infections caused by Pseudomonas aeruginosa. Bosn J Basic Med Sci. 2015 May 25;15(2):15-24. doi: 10.17305/bjbms.2015.292. PMID: 26042508; PMCID: PMC4469931.
In vitro protocol:
1. Zhang X, Liu Y, Lu Y, Li S, Liu J, Zhang Y, Wang L, Li MO, Luo Y, Zhang W, Chen C, Li Y. N-3-(oxododecanoyl)-L-homoserine lactone suppresses dendritic cell maturation by upregulating the long noncoding RNA NRIR. J Biosci. 2021;46:65. PMID: 34219741.
2. Yadav VK, Singh PK, Sharma D, Pandey H, Singh SK, Agarwal V. Autoinducer N-(3-oxododecanoyl)-l-homoserine lactone induces calcium and reactive oxygen species-mediated mitochondrial damage and apoptosis in blood platelets. Microb Pathog. 2021 May;154:104792. doi: 10.1016/j.micpath.2021.104792. Epub 2021 Feb 23. PMID: 33636321.
In vivo protocol:
1. Khambati I, Han S, Pijnenburg D, Jang H, Forsythe P. The bacterial quorum-sensing molecule, N-3-oxo-dodecanoyl-L-homoserine lactone, inhibits mediator release and chemotaxis of murine mast cells. Inflamm Res. 2017 Mar;66(3):259-268. doi: 10.1007/s00011-016-1013-3. Epub 2016 Nov 28. PMID: 27896412.
2. Golpasha ID, Mousavi SF, Owlia P, Siadat SD, Irani S. Immunization with 3-oxododecanoyl-L-homoserine lactone-r-PcrV conjugate enhances survival of mice against lethal burn infections caused by Pseudomonas aeruginosa. Bosn J Basic Med Sci. 2015 May 25;15(2):15-24. doi: 10.17305/bjbms.2015.292. PMID: 26042508; PMCID: PMC4469931.
1: Biswas NN, Kutty SK, Barraud N, Iskander GM, Griffith R, Rice SA, Willcox M, Black DS, Kumar N. Indole-based novel small molecules for the modulation of bacterial signalling pathways. Org Biomol Chem. 2015 Jan 21;13(3):925-37. doi: 10.1039/c4ob02096k. PMID: 25406997.
2: Hong KK, Kim JH, Yoon JH, Park HM, Choi SJ, Song GH, Lee JC, Yang YL, Shin HK, Kim JN, Cho KH, Lee JH. O-Succinyl-L-homoserine-based C4-chemical production: succinic acid, homoserine lactone, γ-butyrolactone, γ-butyrolactone derivatives, and 1,4-butanediol. J Ind Microbiol Biotechnol. 2014 Oct;41(10):1517-24. doi: 10.1007/s10295-014-1499-z. Epub 2014 Aug 26. PMID: 25155257.
