n-Propyl lactate - CAS 616-09-1
Catalog number: 616-09-1
Category: Main Product
Molecular Formula:
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Boiling Point:
174.2ºCat 760 mmHg
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1.Oxamic acid analogues as LDH-C4-specific competitive inhibitors.
Rodríguez-Páez L1, Chena-Taboada MA, Cabrera-Hernández A, Cordero-Martínez J, Wong C. J Enzyme Inhib Med Chem. 2011 Aug;26(4):579-86. doi: 10.3109/14756366.2011.566221. Epub 2011 Mar 25.
We performed kinetic studies to determine whether oxamate analogues are selective inhibitors of LDH-C4, owing to their potential usefulness in fertility control and treatment of some cancers. These substances were shown to be competitive inhibitors of LDH isozymes and are able to discriminate among subtle differences that differentiate the active sites of LDH-A4, LDH-B4 and LDH-C4. N-Ethyl oxamate was the most potent inhibitor showing the highest affinity for LDH-C4. However, N-propyl oxamate was the most selective inhibitor showing a high degree of selectivity towards LDH-C4. Non-polar four carbon atoms chains, linear or branched, dramatically diminished the affinity and selectivity towards LDH-C4. N-Propyl oxamate significantly reduced ATP levels, capacitation and mouse sperm motility, in line with results shown by others, suggesting that LDH-C4 plays an essential role in mouse fertility.
2.Effect of oxamic analogues on functional mice sperm parameters.
Cordero-Martínez J1, Aguirre-Alvarado C, Wong C, Rodríguez-Páez L. Syst Biol Reprod Med. 2014 Aug;60(4):189-98. doi: 10.3109/19396368.2014.902144. Epub 2014 Mar 21.
The present study evaluates the effect of oxamate derivatives (N-ethyl, N-propyl, N-butyl oxamates) on functional murine sperm parameters, towards a new male non-hormonal contraceptive. These derivatives are selective inhibitors of lactate dehydrogenase-C4 (LDH-C4). LDH-C4 is a sperm-specific enzyme that plays an important role in ATP production for maintaining progressive motility as well as to induce capacitation and hyperactivation. The results demonstrate that all oxamate derivatives selectively inhibited LDH-C4 in mouse sperm extracts. The IC(50) values for hexokinase and glyceraldehyde-3-phosphate dehydrogenase were at least an order of magnitude greater than LDH-C4 IC(50) values. Prodrugs of oxamate derivatives assayed on sperm cells diminished normal sperm motility parameters, acrosome reaction, and cell viability in a concentration dependent manner. Also, we performed in vivo studies to determine the potential toxicity and possible contraceptive ability of these inhibitors.
3.The action of n-propyl gallate on gluconeogenesis and oxygen uptake in the rat liver.
Eler GJ1, Peralta RM, Bracht A. Chem Biol Interact. 2009 Oct 30;181(3):390-9. doi: 10.1016/j.cbi.2009.07.006. Epub 2009 Jul 17.
In the present study the metabolic actions of n-propyl gallate on hepatic gluconeogenesis, oxygen uptake and related parameters were investigated. Experiments were done in the isolated perfused rat liver. n-Propyl gallate inhibited gluconeogenesis and stimulated oxygen uptake at concentrations up to 200 microM. The inhibitory effects on lactate gluconeogenesis (ED(50) 86.4 microM) and alanine gluconeogenesis were considerably more pronounced than those on glycerol and fructose gluconeogenesis. n-Propyl gallate also stimulated oxygen uptake in both the mitochondrial (63%) and microsomal (37%) electron transport chains. The first one is due mainly to the oxidation of n-propanol, as a metabolite of the first step of n-propyl gallate transformation. The second one results from a direct stimulation of the microsomal electron transport chain. n-Propyl gallate inhibited pyruvate carboxylation (ED(50) 142.2 microM) in consequence of an inhibition of pyruvate transport into the mitochondria an effect not found for gallic acid.
4.Testis-Specific Lactate Dehydrogenase (LDH-C4) in Skeletal Muscle Enhances a Pika's Sprint-Running Capacity in Hypoxic Environment.
Wang Y1, Wei L2, Wei D3, Li X4, Xu L5, Wei L2. Int J Environ Res Public Health. 2015 Aug 7;12(8):9218-36. doi: 10.3390/ijerph120809218.
LDH-C4 is a lactate dehydrogenase that catalyzes the conversion of pyruvate to lactate. In mammals, ldh-c was originally thought to be expressed only in testis and spermatozoa. Plateau pika (Ochotona curzoniae), which belongs to the genus Ochotona of the Ochotonidea family, is a hypoxia tolerant mammal living 3000-5000 m above sea level on the Qinghai-Tibet Plateau, an environment which is strongly hypoxic. Ldh-c is expressed not only in testis and sperm but also in somatic tissues of plateau pika. In this study, the effects of N-propyl oxamate and N-isopropyl oxamate on LDH isozyme kinetics were compared to screens for a selective inhibitor of LDH-C4. To reveal the role and physiological mechanism of LDH-C4 in skeletal muscle of plateau pika, we investigated the effect of N-isopropyl oxamate on the pika exercise tolerance as well as the physiological mechanism. Our results show that Ki of N-propyl oxamate and N-isopropyl oxamate for LDH-A4, LDH-B4, and LDH-C4 were 0.
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