HEPES

Last updated
HEPES
HEPES.png
Names
Preferred IUPAC name
2-[4-(2-Hydroxyethyl)piperazin-1-yl]ethane-1-sulfonic acid
Other names
HEPES
Identifiers
3D model (JSmol)
883043
ChEBI
ChemSpider
ECHA InfoCard 100.028.098 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 230-907-9
PubChem CID
RTECS number
  • TL6809000
UNII
  • InChI=1S/C8H18N2O4S/c11-7-5-9-1-3-10(4-2-9)6-8-15(12,13)14/h11H,1-8H2,(H,12,13,14) Yes check.svgY
    Key: JKMHFZQWWAIEOD-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H18N2O4S/c11-7-5-9-1-3-10(4-2-9)6-8-15(12,13)14/h11H,1-8H2,(H,12,13,14)
    Key: JKMHFZQWWAIEOD-UHFFFAOYAC
  • OCCN1CC[NH+](CCS(=O)([O-])=O)CC1
Properties
C8H18N2O4S
Molar mass 238.3012 g/mol
Appearancewhite crystalline powder
Density Not applicable
Melting point >234-238°C (453-457K)
40 g/100 ml (20°C)
Acidity (pKa)3 (pKa1),
7.5 (pKa2) [1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Eye Irritant
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)
1
0
1
Flash point Non-flammable
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

HEPES (4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid) is a zwitterionic sulfonic acid buffering agent; one of the twenty Good's buffers. HEPES is widely used in cell culture, largely because it is better at maintaining physiological pH despite changes in carbon dioxide concentration (produced by aerobic respiration) when compared to bicarbonate buffers, which are also commonly used in cell culture. [2] Lepe-Zuniga et al. reported an unwanted photochemical process wherein HEPES catalyzes a reaction with riboflavin when exposed to ambient light to produce hydrogen peroxide. [3] [4] This is not a problem in bicarbonate-based cell culture buffers. It is therefore strongly advised to keep solutions containing both HEPES and riboflavin in darkness as much as possible to prevent oxidation.

HEPES has the following characteristics:

HEPES has negligible metal ion binding, [5] making it a good choice as a buffer for enzymes which might be inhibited by metal chelation.

See also

Related Research Articles

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3
.

<span class="mw-page-title-main">Carbonate</span> Salt of carbonic acid

A carbonate is a salt of carbonic acid (H2CO3), characterized by the presence of the carbonate ion, a polyatomic ion with the formula CO2−3. The word carbonate may also refer to a carbonate ester, an organic compound containing the carbonate group C(=O)(O–)2.

pH Measure of the level of acidity or basicity of an aqueous solution

In chemistry, pH, also referred to as acidity, historically denotes "potential of hydrogen". It is a scale used to specify the acidity or basicity of an aqueous solution. Acidic solutions are measured to have lower pH values than basic or alkaline solutions.

A buffer solution is an acid or a base aqueous solution consisting of a mixture of a weak acid and its conjugate base, or vice versa. Its pH changes very little when a small amount of strong acid or base is added to it. Buffer solutions are used as a means of keeping pH at a nearly constant value in a wide variety of chemical applications. In nature, there are many living systems that use buffering for pH regulation. For example, the bicarbonate buffering system is used to regulate the pH of blood, and bicarbonate also acts as a buffer in the ocean.

<span class="mw-page-title-main">Citric acid</span> Weak organic acid

Citric acid is an organic compound with the chemical formula HOC(CO2H)(CH2CO2H)2. It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in the metabolism of all aerobic organisms.

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<span class="mw-page-title-main">Tris</span> Chemical compound

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<span class="mw-page-title-main">PIPES</span> Chemical compound

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<span class="mw-page-title-main">MOPS</span> Chemical compound

MOPS (3-(N-morpholino)propanesulfonic acid) is a buffer introduced in the 1960s, one of the twenty Good's buffers. It is a structural analog to MES, and like MES, its structure contains a morpholine ring. HEPES is a similar pH buffering compound that contains a piperazine ring. With a pKa of 7.20, MOPS is an excellent buffer for many biological systems at near-neutral pH.

<span class="mw-page-title-main">MES (buffer)</span> Chemical compound

MES is the common name for the compound 2-(N-morpholino)ethanesulfonic acid. Its chemical structure contains a morpholine ring. It has a molecular weight of 195.2 and the chemical formula is C6H13NO4S. Synonyms include: 2-morpholinoethanesulfonic acid; 2-(4-morpholino)ethanesulfonic acid; 2-(N-morpholino)ethanesulfonic acid; 2-(4-morpholino)ethanesulfonic acid; MES; MES hydrate; and morpholine-4-ethanesulfonic acid hydrate. MOPS is a similar pH buffering compound which contains a propanesulfonic moiety instead of an ethanesulfonic one.

Acid–base homeostasis is the homeostatic regulation of the pH of the body's extracellular fluid (ECF). The proper balance between the acids and bases in the ECF is crucial for the normal physiology of the body—and for cellular metabolism. The pH of the intracellular fluid and the extracellular fluid need to be maintained at a constant level.

<span class="mw-page-title-main">Bicarbonate buffer system</span> Buffer system that maintains pH balance in humans

The bicarbonate buffer system is an acid-base homeostatic mechanism involving the balance of carbonic acid (H2CO3), bicarbonate ion (HCO
3
), and carbon dioxide (CO2) in order to maintain pH in the blood and duodenum, among other tissues, to support proper metabolic function. Catalyzed by carbonic anhydrase, carbon dioxide (CO2) reacts with water (H2O) to form carbonic acid (H2CO3), which in turn rapidly dissociates to form a bicarbonate ion (HCO
3
) and a hydrogen ion (H+) as shown in the following reaction:

<span class="mw-page-title-main">Carbamoyl phosphate synthetase</span> Class of enzymes

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<span class="mw-page-title-main">Carbonic anhydrase</span> Class of enzymes

The carbonic anhydrases form a family of enzymes that catalyze the interconversion between carbon dioxide and water and the dissociated ions of carbonic acid. The active site of most carbonic anhydrases contains a zinc ion. They are therefore classified as metalloenzymes. The enzyme maintains acid-base balance and helps transport carbon dioxide.

Cell isolation is the process of separating individual living cells from a solid block of tissue or cell suspension. While some types of cell naturally exist in a separated form, other cell types that are found in solid tissue require specific techniques to separate them into individual cells. This may be performed by using enzymes to digest the proteins that binds these cells together within the extracellular matrix. After the matrix proteins have been digested, cells remain loosely bound together but can be gently separated mechanically. Following isolation, experiments can be performed on these single isolated cells including patch clamp electrophysiology, calcium fluorescence imaging, and immunocytochemistry. 

References

  1. Johnson MA, Seifert S, Petrache HI, Kimble-Hill AC (2014). "Phase Coexistence in Single-Lipid Membranes Induced by Buffering Agents". Langmuir. 30 (33): 9880–9885. doi:10.1021/la5018938. PMC   4148158 .
  2. Baicu SC, Taylor MJ (2002). "Acid-base buffering in organ preservation solutions as a function of temperature: new parameters for comparing buffer capacity and efficiency". Cryobiology. 45 (1): 33–48. doi:10.1016/S0011-2240(02)00104-9. PMID   12445548.
  3. Lepe-Zuniga JL, Zigler JS, Gery I (October 1987). "Toxicity of light-exposed Hepes media". Journal of Immunological Methods. 103 (1): 145. doi:10.1016/0022-1759(87)90253-5. PMID   3655381.
  4. Zigler JS, Lepe-Zuniga JL, Vistica B, Gery I (May 1985). "Analysis of the cytotoxic effects of light-exposed HEPES-containing culture medium". In Vitro Cellular & Developmental Biology. 21 (5): 282–7. doi:10.1007/BF02620943. PMID   4019356. S2CID   6557697.
  5. "Hopax Fine Chemicals - Biological buffers and their interactions with metal ions".