Lactone

N-phenylacetyl-L-Homoserine lactone attenuates the group sensing of the pathogen Acinetobacter baumannii and can be used to study bacterial infections.

N-(3-Hydroxytetradecanoyl)-DL-homoserine lactone [has antibacterial activity].

3-Desacetyl Cefotaxime lactone, the active metabolite of Cefotaxime, is derived from its sodium salt form, which is recognized as a third-generation cephalosporin antibiotic.

MAC glucuronide α-hydroxy lactone-linked SN-38 (Topoisomerase I inhibitor) is a cytotoxic drug linker that maintains a stabilized lactone form, demonstrating efficacy against L540cy and Ramos cells with IC50 values of 99 and 105 ng/mL, respectively[1].

(3R,5R)-Rosuvastatin Lactone is an isomer of Rosuvastatin Lactone.

N-(3-Oxooctanoyl)-DL-homoserine lactone exhibits stereochemistry-dependent growth regulatory activity for roots.

(±)5(6)-DiHET lactone is a 1,5 cyclic ester derived from (±)5(6)-DiHET , which, in turn, is a potential derivative of epoxidation of arachidonic acid at the α-5 double bond. (±)4(5)-DiHDPA lactone is a derivative of docosahexaenoic acid that is analogous to (±)5(6)-DiHET lactone. It is the 1,4 cyclic ester derived from (±)4(5)-DiHDPA, which is produced by epoxidation of DHA at the α-4 double bond. Its biological activity is unknown.

Prostaglandin F2α 1,11-lactone (PGF2α 1,11-lactone) is a lipid-soluble prodrug of Prostaglandin F2α and can be used in studies about treating glaucoma. Prostaglandin F2α 1,11-lactone is active as an antifertility agent with greatly reduced vasoactivity.

PGF2α 1,15-lactone is a lipid-soluble internal ester of PGF2α. Hydrolysis of the lactone readily produces free PGF2α in plasma. In rhesus monkeys, a total dose of 15 mg of PGF2α 1,15-lactone terminates early pregnancy, whereas PGF2α is ineffective.

N-3-oxo-hexadecanoyl-L-Homoserine lactone is an unusual, substituted, long-chain N-acyl-homoserine lactone (AHL) produced by some bacteria, including strains of Agrobacterium vitis and Pseudomonas. Like other AHLs, this C16-containing form is thought to be involved in quorum sensing. Substituted, long-chain AHLs, including N-3-oxo-tetradecanoyl-L-homoserine lactone , prime for systemic acquired resistance to pathogen attack in plants.

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-3-oxo-tetradecanoyl-L-homoserine lactone (3-oxo-C14-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria.[1] [2] [3] It appears later than shorter acyl chain AHLs in developing biofilms [4] and, like other long chain 3-oxo-AHLs, stimulates the production of putisolvin, [5] which in turn, inhibits biofilm formation.

Pravastatin lactone is a metabolite of pravastatin , a hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase inhibitor that is a ring-hydroxylated metabolite of mevastatin . Pravastatin lactone is formed when pravastatin undergoes acid-catalyzed non-enzymatic lactonization in the stomach following oral administration.

5(S)-HETE lactone is a cyclic ester formed by acid-catalyzed nucleophilic addition of the C-5 hydroxyl to the C-1 carboxyl of 5(S)-HETE. The ability of (±)5-HETE lactone to inhibit rat basophilic leukemia cell 5-lipoxygenase (IC50 = 27 μM) may be entirely due to the 5(S) isomer, but the enantiomers have not been tested separately.

Quorum sensing is a regulatory process used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group) and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. C18:1-δ9 cis-(L)-HSL is a long-chain AHL that may have antimicrobial activity and thus, might be used to inhibit pathogenesis by regulating bacerial quorum sensing signaling.

Quorum sensing is a regulatory process used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group) and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. C14:1-δ9-cis-(L)-HSL is a long-chain AHL that functions as a signaling molecule in the quorum sensing of A. vitis. Regulating bacterial quorum sensing signaling can be used to inhibit pathogenesis and thus, represents a new approach to antimicrobial therpy in the treatment of infectious diseases.

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density.[1] This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production.[2] Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases.[3] AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group), and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family.[4] C16-HSL is one of a number of lipophilic, long acyl side-chain bearing AHLs, including its monounsaturated analog C16:1-(L)-HSL, produced by the LuxI AHL synthase homolog SinI involved in quorum-sensing signaling in S. meliloti, a nitrogen-fixing bacterial symbiont of certain legumes.[5],[6] C16-HSL is the most abundant AHL produced by the proteobacterium R. capsulatus and activates genetic exchange between R. capsulatus cells.[7] N-Hexadecanoyl-L-homoserine lactone and other hydrophobic AHLs tend to localize in relatively lipophilic cellular environments of bacteria and cannot diffuse freely through the cell membrane. The long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or may be transported between communicating cells by way of extracellular outer membrane vesicles.[8],[9]Reference:[1]. González, J.E., and Keshavan, N.D. Messing with bacterial quorum sensing Microbiol. Mol. Biol. Rev. 70(4), 859-875 (2006).[2]. Gould, T.A., Herman, J., Krank, J., et al. Specificity of acyl-homoserine lactone syntheses examined by mass spectrometry Journal of Bacteriology 188(2), 773-783 (2006).[3]. Cegelski, L., Marshall, G.R., Eldridge, G.R., et al. The biology and future prospects of antivirulence therapies Nature Reviews.Microbiology 6(1), 17-27 (2008).[4]. Penalver, C.G.N., Morin, D., Cantet, F., et al. Methylobacterium extorquens AM1 produces a novel type of acyl-homoserine lactone with a double unsaturated side chain under methylotrophic growth conditions FEBS Letters 580, 561-567 (2006).[5]. Gao, M., Chen, H., Eberhard, A., et al. sinI- and expR-dependent quorum sensing in Sinorhizobium meliloti Journal of Bacteriology 187(23), 7931-7944 (2005).[6]. Teplitski, M., Eberhard, A., Gronquist, M.R., et al. Chemical identification of N-acyl homoserine lactone quorum-sensing signals produced by Sinorhizobium meliloti strains in defined medium Archives of Microbiology 180, 494-497 (2003).[7]. Schaefer, A.L., Taylor, T.A., Beatty, J.T., et al. Long-chain acyl-homoserine lactone quorum-sensing regulation of Rhodobacter capsulatus gene transfer agent production Journal of Bacteriology 184(23), 6515-6521 (2002).[8]. Pearson, J.P., Van Delden, C., and Iglewski, B.H. Active efflux and diffusion are involved in transport of Pseudomonas aeruginosa cell-to-cell signals Journal of Bacteriology 181(4), 1203-1210 (1999).[9]. Mashburn-Warren, L., and Whiteley, M. Special delivery: Vesicle trafficking in prokaryotes Molecular Microbiology 61(4), 839-846 (2006).

C18-HSL is one of four lipophilic, long acyl side-chain-bearing N-acylated homoserine lactones (AHLs) produced by the LuxI AHL synthase homolog SinI, involved in quorum sensing signaling in S. meliloti, a nitrogen-fixing bacterial symbiont of the legume [M. sativa]. C18-HSL and other hydrophobic AHLs tend to localize in relatively lipophilic cellular environments and cannot diffuse freely through the cell membrane. These long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or transported between communicating cells via extracellular outer membrane vesicles. Quorum sensing, a regulatory system used by bacteria to control gene expression in response to cell density, manifests in phenotypes such as biofilm formation and virulence factor production. Coordinated gene expression is achieved through the production, release, and detection of small diffusible signal molecules called autoinducers, including AHLs, which vary in acyl group length (C4-C18), C3 substitution (hydrogen, hydroxyl, or oxo group), and the presence or absence of carbon-carbon double bonds, conferring signal specificity through LuxR family transcriptional regulators. Regulation of bacterial quorum sensing signaling to inhibit pathogenesis represents a novel approach to antimicrobial therapy in treating infectious diseases.

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases. AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group), and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. N-tridecanoyl-L-Homoserine lactone (C13-HSL) possesses a rare odd-numbered acyl carbon chain and is produced by wild-type and mutant strains of Y. pseudotuberculosis in trace amounts.

N-acylated homoserine lactones (AHLs) are a class of autoinducers used in bacterial quorum sensing to control gene expression in response to cell density. These molecules, comprising a fatty acid coupled with homoserine lactone (HSL), vary in acyl group length (C4-C18), C3 substitution (hydrogen, hydroxyl, or oxo group), and the presence of carbon-carbon double bonds, determining signal specificity through LuxR family transcriptional regulators. C11-HSL, with its rare odd-numbered acyl carbon chain, may act as a minor quorum-sensing signaling molecule in P. aeruginosa strains. Regulating bacterial quorum sensing can inhibit pathogenesis and represents a novel antimicrobial therapy approach for infectious diseases.

2-Hydroxy atorvastatin lactone, a metabolite of Atorvastatin, is an orally active HMG-CoA reductase inhibitor that efficiently reduces blood lipids [1][2].

Olmesartan lactone impurity is a cyclic ester impurity derived from Olmesartan, an angiotensin II receptor (AT1R) antagonist with potential applications in the study of high blood pressure.

Indinavir lactone is a protease inhibitor used as a component of highly active antiretroviral therapy to treat HIV/AIDS.

Cerivastatin lactone is a metabolite of a competitive inhibitor of HMG-CoA reductase, Cerivastatin. Cerivastatin lactone shows inhibitory effects on CYP3A4/5 activity.

Calcitriol lactone (1α,25-Dihydroxyvitamin D3-26,23-lactone), a vitamin D3 metabolite, serves as the active form of vitamin D, influencing bone health, cell differentiation, and immune function.