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)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
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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In inorganic chemistry, bicarbonate is an intermediate form in the deprotonation of carbonic acid. It is a polyatomic anion with the chemical formula HCO
3
.

<span class="mw-page-title-main">Carbonate</span> Salt or ester 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 groupO=C(−O−)2.

A buffer solution is a solution where the pH does not change significantly on dilution or if an acid or base is added at constant temperature. 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">Soil pH</span> Measure of how acidic or alkaline the soil is

Soil pH is a measure of the acidity or basicity (alkalinity) of a soil. Soil pH is a key characteristic that can be used to make informative analysis both qualitative and quantitatively regarding soil characteristics. pH is defined as the negative logarithm (base 10) of the activity of hydronium ions in a solution. In soils, it is measured in a slurry of soil mixed with water, and normally falls between 3 and 10, with 7 being neutral. Acid soils have a pH below 7 and alkaline soils have a pH above 7. Ultra-acidic soils and very strongly alkaline soils are rare.

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

Sodium bicarbonate (IUPAC name: sodium hydrogencarbonate), commonly known as baking soda or bicarbonate of soda, is a chemical compound with the formula NaHCO3. It is a salt composed of a sodium cation (Na+) and a bicarbonate anion (HCO3). Sodium bicarbonate is a white solid that is crystalline but often appears as a fine powder. It has a slightly salty, alkaline taste resembling that of washing soda (sodium carbonate). The natural mineral form is nahcolite, although it is more commonly found as a component of the mineral trona.

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

Ethylenediaminetetraacetic acid (EDTA), also called EDTA acid after its own abbreviation, is an aminopolycarboxylic acid with the formula [CH2N(CH2CO2H)2]2. This white, water-insoluble solid is widely used to bind to iron (Fe2+/Fe3+) and calcium ions (Ca2+), forming water-soluble complexes even at neutral pH. It is thus used to dissolve Fe- and Ca-containing scale as well as to deliver iron ions under conditions where its oxides are insoluble. EDTA is available as several salts, notably disodium EDTA, sodium calcium edetate, and tetrasodium EDTA, but these all function similarly.

<span class="mw-page-title-main">His-tag</span> Molecular biology technique

A polyhistidine-tag, best known by the trademarked name His-tag, is an amino acid motif in proteins that typically consists of at least six histidine (His) residues, often at the N- or C-terminus of the protein. It is also known as a hexa histidine-tag, 6xHis-tag, or His6 tag. The tag was invented by Roche, although the use of histidines and its vectors are distributed by Qiagen. Various purification kits for histidine-tagged proteins are commercially available from multiple companies.

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

Tris, or tris(hydroxymethyl)aminomethane, or known during medical use as tromethamine or THAM, is an organic compound with the formula (HOCH2)3CNH2. It is extensively used in biochemistry and molecular biology as a component of buffer solutions such as in TAE and TBE buffers, especially for solutions of nucleic acids. It contains a primary amine and thus undergoes the reactions associated with typical amines, e.g., condensations with aldehydes. Tris also complexes with metal ions in solution. In medicine, tromethamine is occasionally used as a drug, given in intensive care for its properties as a buffer for the treatment of severe metabolic acidosis in specific circumstances. Some medications are formulated as the "tromethamine salt" including Hemabate (carboprost as trometamol salt), and "ketorolac trometamol". In 2023 a strain of Pseudomonas hunanensis was found to be able to degrade TRIS buffer.

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Good's buffers are twenty buffering agents for biochemical and biological research selected and described by Norman Good and colleagues during 1966–1980. Most of the buffers were new zwitterionic compounds prepared and tested by Good and coworkers for the first time, though some were known compounds previously overlooked by biologists. Before Good's work, few hydrogen ion buffers between pH 6 and 8 had been accessible to biologists, and very inappropriate, toxic, reactive and inefficient buffers had often been used. Many Good's buffers became and remain crucial tools in modern biological laboratories.

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

PIPES is a frequently used buffering agent in biochemistry. It is an ethanesulfonic acid buffer developed by Good et al. in the 1960s.

<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 (2-(N-morpholino)ethanesulfonic acid) is a chemical compound that contains a morpholine ring. It has a molecular weight of 195.2 g/mol 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

Carbamoyl phosphate synthetase catalyzes the ATP-dependent synthesis of carbamoyl phosphate from glutamine or ammonia and bicarbonate. This enzyme catalyzes the reaction of ATP and bicarbonate to produce carboxy phosphate and ADP. Carboxy phosphate reacts with ammonia to give carbamic acid. In turn, carbamic acid reacts with a second ATP to give carbamoyl phosphate plus ADP.

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<span class="mw-page-title-main">Acid–base disorder</span> Abnormality of the human bodys normal balance of acids and bases

Acid–base imbalance is an abnormality of the human body's normal balance of acids and bases that causes the plasma pH to deviate out of the normal range. In the fetus, the normal range differs based on which umbilical vessel is sampled. It can exist in varying levels of severity, some life-threatening.

The isohydric principle is the phenomenon whereby multiple acid/base pairs in solution will be in equilibrium with one another, tied together by their common reagent: the hydrogen ion and hence, the pH of solution. That is, when several buffers are present together in the same solution, they are all exposed to the same hydrogen ion activity. Hence, the pK of each buffer will dictate the ratio of the concentrations of its base and weak acid forms at the given pH, in accordance with the Henderson-Hasselbalch equation.

<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.

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".