Oligopeptide P11-4

Last updated
Oligopeptide P11-4
Oligopetide P11-4.png
Names
IUPAC name
(4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-carbamimidamido-2-[[(2S)-2-[[(2S)-1,5-dihydroxy-2-(1-hydroxyethylideneamino)-5-iminopentylidene]amino]-1,5-dihydroxy-5-iminopentylidene]amino]-1-hydroxypentylidene]amino]-1-hydroxy-3-phenylpropylidene]amino]-4-carboxy-1-hydroxybutylidene]amino]-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino]-4-carboxy-1-hydroxybutylidene]amino]-1-hydroxy-3-phenylpropylidene]amino]-5-[(2S)-1-[(2S)-1,5-dihydroxy-1,5-diiminopentan-2-yl]imino-1,5-dihydroxy-5-iminopentan-2-yl]imino-5-hydroxypentanoic acid
Other names
  • oligopeptide 104 Ac-Gln-Gln-Arg-Phe-Glu-Trp-Glu-Phe-Glu-Gln-Gln-NH2 Ace-QQRFEWEFEQQ-NH2
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C72H98N20O22/c1-37(93)82-45(19-26-55(74)95)63(106)85-47(21-28-57(76)97)65(108)84-44(17-10-32-80-72(78)79)62(105)90-51(33-38-11-4-2-5-12-38)69(112)88-50(24-31-60(102)103)68(111)92-53(35-40-36-81-42-16-9-8-15-41(40)42)71(114)89-49(23-30-59(100)101)67(110)91-52(34-39-13-6-3-7-14-39)70(113)87-48(22-29-58(98)99)66(109)86-46(20-27-56(75)96)64(107)83-43(61(77)104)18-25-54(73)94/h2-9,11-16,36,43-53,81H,10,17-35H2,1H3,(H2,73,94)(H2,74,95)(H2,75,96)(H2,76,97)(H2,77,104)(H,82,93)(H,83,107)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,112)(H,89,114)(H,90,105)(H,91,110)(H,92,111)(H,98,99)(H,100,101)(H,102,103)(H4,78,79,80)/t43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-/m0/s1
    Key: SMSPMXWRKWKZBG-ZOOWYRFPSA-N
  • InChI=1/C72H98N20O22/c1-37(93)82-45(19-26-55(74)95)63(106)85-47(21-28-57(76)97)65(108)84-44(17-10-32-80-72(78)79)62(105)90-51(33-38-11-4-2-5-12-38)69(112)88-50(24-31-60(102)103)68(111)92-53(35-40-36-81-42-16-9-8-15-41(40)42)71(114)89-49(23-30-59(100)101)67(110)91-52(34-39-13-6-3-7-14-39)70(113)87-48(22-29-58(98)99)66(109)86-46(20-27-56(75)96)64(107)83-43(61(77)104)18-25-54(73)94/h2-9,11-16,36,43-53,81H,10,17-35H2,1H3,(H2,73,94)(H2,74,95)(H2,75,96)(H2,76,97)(H2,77,104)(H,82,93)(H,83,107)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,112)(H,89,114)(H,90,105)(H,91,110)(H,92,111)(H,98,99)(H,100,101)(H,102,103)(H4,78,79,80)/t43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-/m0/s1
    Key: SMSPMXWRKWKZBG-ZOOWYRFPBV
  • CC(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc2c[nH]c3c2cccc3)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc4ccccc4)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N
Properties
C72H98N20O22
Molar mass 1595.694 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Oligopeptide P11-4 is a synthetic, pH controlled self-assembling peptide used for biomimetic mineralization e.g. for enamel regeneration [1] or as an oral care agent. P11-4 (INCI name Oligopeptide 104) consists of the natural occurring amino acids Glutamine, Glutamic acid, Phenylalanine, Tryptophan and Arginine. [2] The resulting higher molecular structure has a high affinity to tooth mineral. [3] P11-4 has been developed and patented by The University of Leeds (UK). The Swiss company Credentis has licensed the peptide technology and markets it under the trade names including CUROLOX, REGENAMEL, and EMOFLUOR. They offer three products with this technology. [4] As of June 2016 in Switzerland products are available with new Brand names from Dr. Wild & Co AG. [5]

Contents

Mechanism of action

P11-4 is an α-peptide that self-assembles into β-sheet amyloids with a hydrogel appearance at low pH. [6] It builds a 3-D bio-matrix with binding sites for calcium ions serving as nucleation point for hydroxyapatite (tooth mineral) formation. The high affinity to tooth mineral is based on matching distances of Ca-ion binding sites on P11-4 and Ca spacing in the crystal lattice of hydroxyapatite. The matrix formation is pH controlled and thus allows control matrix activity and place of formation.

P11-4 in dental applications

Self assembling properties of P11-4 are used to regenerate early caries lesions. By application of P11-4 on the tooth surface, the peptide diffuse through the intact hypomineralized plate into the early caries lesion body and start, due to the low pH in such a lesion, to self-assemble generating a peptide scaffold mimicking the enamel matrix. Around the newly formed matrix de-novo enamel-crystals are formed from calcium phosphate present in saliva. Through the remineralization caries activity is significantly reduced in comparison with a fluoride treatment alone. [7] In aqueous oral care gels the peptide is present as matrix. It binds directly as matrix to the tooth mineral and forms a stable layer on the teeth. [8] This layer does protect the teeth from acid attacks. It also occludes open dentin tubules and thus reduces the dental sensitivity.

Uses

Availability

Availability of products containing P11-4 vary by country, with some products available only to dentists, and others available to the retail public.

Medical device for caries treatment and enamel regeneration:

Cosmetic products for acid protection and dentin desensitization:

See also

Related Research Articles

<span class="mw-page-title-main">Human tooth</span> Calcified whitish structure in humans mouths used to break down food

Human teeth function to mechanically break down items of food by cutting and crushing them in preparation for swallowing and digesting. As such, they are considered part of the human digestive system. Humans have four types of teeth: incisors, canines, premolars, and molars, which each have a specific function. The incisors cut the food, the canines tear the food and the molars and premolars crush the food. The roots of teeth are embedded in the maxilla or the mandible and are covered by gums. Teeth are made of multiple tissues of varying density and hardness.

<span class="mw-page-title-main">Toothpaste</span> Substance to clean and maintain teeth

Toothpaste is a paste or gel dentifrice used with a toothbrush to clean and maintain the aesthetics and health of teeth. Toothpaste is used to promote oral hygiene: it is an abrasive that aids in removing dental plaque and food from the teeth, assists in suppressing halitosis, and delivers active ingredients to help prevent tooth decay and gum disease (gingivitis). Owing to differences in composition and fluoride content, not all toothpastes are equally effective in maintaining oral health. The decline of tooth decay during the 20th century has been attributed to the introduction and regular use of fluoride-containing toothpastes worldwide. Large amounts of swallowed toothpaste can be poisonous. Common colors for toothpaste include white and blue.

<span class="mw-page-title-main">Tooth enamel</span> Major tissue that makes up part of the tooth in humans and many animals

Tooth enamel is one of the four major tissues that make up the tooth in humans and many animals, including some species of fish. It makes up the normally visible part of the tooth, covering the crown. The other major tissues are dentin, cementum, and dental pulp. It is a very hard, white to off-white, highly mineralised substance that acts as a barrier to protect the tooth but can become susceptible to degradation, especially by acids from food and drink. In rare circumstances enamel fails to form, leaving the underlying dentin exposed on the surface.

<span class="mw-page-title-main">Tooth decay</span> Deformation of teeth due to acids produced by bacteria

Tooth decay, also known as cavities or caries, is the breakdown of teeth due to acids produced by bacteria. The cavities may be a number of different colors from yellow to black. Symptoms may include pain and difficulty with eating. Complications may include inflammation of the tissue around the tooth, tooth loss and infection or abscess formation.

<span class="mw-page-title-main">Dentin</span> Calcified tissue of the body; one of the four major components of teeth

Dentin or dentine is a calcified tissue of the body and, along with enamel, cementum, and pulp, is one of the four major components of teeth. It is usually covered by enamel on the crown and cementum on the root and surrounds the entire pulp. By volume, 45% of dentin consists of the mineral hydroxyapatite, 33% is organic material, and 22% is water. Yellow in appearance, it greatly affects the color of a tooth due to the translucency of enamel. Dentin, which is less mineralized and less brittle than enamel, is necessary for the support of enamel. Dentin rates approximately 3 on the Mohs scale of mineral hardness. There are two main characteristics which distinguish dentin from enamel: firstly, dentin forms throughout life; secondly, dentin is sensitive and can become hypersensitive to changes in temperature due to the sensory function of odontoblasts, especially when enamel recedes and dentin channels become exposed.

<span class="mw-page-title-main">Dental erosion</span> Medical condition

Acid erosion is a type of tooth wear. It is defined as the irreversible loss of tooth structure due to chemical dissolution by acids not of bacterial origin. Dental erosion is the most common chronic condition of children ages 5–17, although it is only relatively recently that it has been recognised as a dental health problem. There is generally widespread ignorance of the damaging effects of acid erosion; this is particularly the case with erosion due to consumption of fruit juices because they tend to be considered as healthy. Acid erosion begins initially in the enamel, causing it to become thin, and can progress into dentin, giving the tooth a dull yellow appearance and leading to dentin hypersensitivity.

<span class="mw-page-title-main">Hydroxyapatite</span> Naturally occurring mineral form of calcium apatite

Hydroxyapatite is a naturally occurring mineral form of calcium apatite with the formula Ca5(PO4)3(OH), often written Ca10(PO4)6(OH)2 to denote that the crystal unit cell comprises two entities. It is the hydroxyl endmember of the complex apatite group. The OH− ion can be replaced by fluoride or chloride, producing fluorapatite or chlorapatite. It crystallizes in the hexagonal crystal system. Pure hydroxyapatite powder is white. Naturally occurring apatites can, however, also have brown, yellow, or green colorations, comparable to the discolorations of dental fluorosis.

<span class="mw-page-title-main">Fluoride therapy</span> Medical use of fluoride

Fluoride therapy is the use of fluoride for medical purposes. Fluoride supplements are recommended to prevent tooth decay in children older than six months in areas where the drinking water is low in fluoride. It is typically used as a liquid, pill, or paste by mouth. Fluoride has also been used to treat a number of bone diseases.

Dentinogenesis is the formation of dentin, a substance that forms the majority of teeth. Dentinogenesis is performed by odontoblasts, which are a special type of biological cell on the outer wall of dental pulps, and it begins at the late bell stage of a tooth development. The different stages of dentin formation after differentiation of the cell result in different types of dentin: mantle dentin, primary dentin, secondary dentin, and tertiary dentin.

A caries vaccine is a vaccine to prevent and protect against tooth decay. Streptococcus mutans has been identified as the major etiological agent of human dental caries. The development of a vaccine for tooth decay has been under investigation since the 1970s. In 1972, a caries vaccine was said to be in animal testing in England, and that it would have begun human testing soon. However, intrinsic difficulties in developing it, coupled with lack of strong economic interests, are the reasons why still no such vaccine is commercially available today. Several types of vaccines are being developed at research centres, with some kind of caries vaccines being considered to diminish or prevent dental caries' impact on young people.

Dentin hypersensitivity is dental pain which is sharp in character and of short duration, arising from exposed dentin surfaces in response to stimuli, typically thermal, evaporative, tactile, osmotic, chemical or electrical; and which cannot be ascribed to any other dental disease.

<span class="mw-page-title-main">Glass ionomer cement</span> Material used in dentistry as a filling material and luting cement

A glass ionomer cement (GIC) is a dental restorative material used in dentistry as a filling material and luting cement, including for orthodontic bracket attachment. Glass-ionomer cements are based on the reaction of silicate glass-powder and polyacrylic acid, an ionomer. Occasionally water is used instead of an acid, altering the properties of the material and its uses. This reaction produces a powdered cement of glass particles surrounded by matrix of fluoride elements and is known chemically as glass polyalkenoate. There are other forms of similar reactions which can take place, for example, when using an aqueous solution of acrylic/itaconic copolymer with tartaric acid, this results in a glass-ionomer in liquid form. An aqueous solution of maleic acid polymer or maleic/acrylic copolymer with tartaric acid can also be used to form a glass-ionomer in liquid form. Tartaric acid plays a significant part in controlling the setting characteristics of the material. Glass-ionomer based hybrids incorporate another dental material, for example resin-modified glass ionomer cements (RMGIC) and compomers.

Biomimetic materials are materials developed using inspiration from nature. This may be useful in the design of composite materials. Natural structures have inspired and innovated human creations. Notable examples of these natural structures include: honeycomb structure of the beehive, strength of spider silks, bird flight mechanics, and shark skin water repellency. The etymological roots of the neologism "biomimetic" derive from Greek, since bios means "life" and mimetikos means "imitative".

Olaflur is a fluoride-containing substance that is an ingredient of toothpastes and solutions for the prevention of dental caries. It has been in use since 1966. Especially in combination with dectaflur, it is also used in the form of gels for the treatment of early stages of caries, sensitive teeth, and by dentists for the refluoridation of damaged tooth enamel.

<span class="mw-page-title-main">Fluoride varnish</span> Highly concentrated form of fluoride

Fluoride varnish is a highly concentrated form of fluoride which is applied to the tooth's surface, by a dentist, dental hygienist or other health care professional, as a type of topical fluoride therapy. It is not a permanent varnish but due to its adherent nature it is able to stay in contact with the tooth surface for several hours. It may be applied to the enamel, dentine or cementum of the tooth and can be used to help prevent decay, remineralise the tooth surface and to treat dentine hypersensitivity. There are more than 30 fluoride-containing varnish products on the market today, and they have varying compositions and delivery systems. These compositional differences lead to widely variable pharmacokinetics, the effects of which remain largely untested clinically.

Amorphous calcium phosphate (ACP) is a glassy solid that is formed from the chemical decomposition of a mixture of dissolved phosphate and calcium salts (e.g. (NH4)2HPO4 + Ca(NO3)2). The resulting amorphous mixture consists mostly of calcium and phosphate, but also contains varying amounts of water and hydrogen and hydroxide ions, depending on the synthesis conditions. Such mixtures are also known as calcium phosphate cement.

<span class="mw-page-title-main">Remineralisation of teeth</span>

Tooth remineralization is the natural repair process for non-cavitated tooth lesions, in which calcium, phosphate and sometimes fluoride ions are deposited into crystal voids in demineralised enamel. Remineralization can contribute towards restoring strength and function within tooth structure.

<span class="mw-page-title-main">Enamel hypoplasia</span> Medical condition

Enamel hypoplasia is a defect of the teeth in which the enamel is deficient in quantity, caused by defective enamel matrix formation during enamel development, as a result of inherited and acquired systemic condition(s). It can be identified as missing tooth structure and may manifest as pits or grooves in the crown of the affected teeth, and in extreme cases, some portions of the crown of the tooth may have no enamel, exposing the dentin. It may be generalized across the dentition or localized to a few teeth. Defects are categorized by shape or location. Common categories are pit-form, plane-form, linear-form, and localised enamel hypoplasia. Hypoplastic lesions are found in areas of the teeth where the enamel was being actively formed during a systemic or local disturbance. Since the formation of enamel extends over a long period of time, defects may be confined to one well-defined area of the affected teeth. Knowledge of chronological development of deciduous and permanent teeth makes it possible to determine the approximate time at which the developmental disturbance occurred. Enamel hypoplasia varies substantially among populations and can be used to infer health and behavioural impacts from the past. Defects have also been found in a variety of non-human animals.

<span class="mw-page-title-main">Pulp capping</span> Dental restoration technique

Pulp capping is a technique used in dental restorations to prevent the dental pulp from necrosis, after being exposed, or nearly exposed during a cavity preparation, from a traumatic injury, or by a deep cavity that reaches the center of the tooth causing the pulp to die. When dental caries is removed from a tooth, all or most of the infected and softened enamel and dentin are removed. This can lead to the pulp of the tooth either being exposed or nearly exposed which causes pulpitis (inflammation). Pulpitis, in turn, can become irreversible, leading to pain and pulp necrosis, and necessitating either root canal treatment or extraction. The ultimate goal of pulp capping or stepwise caries removal is to protect a healthy dental pulp and avoid the need for root canal therapy.

Hard tissue, refers to "normal" calcified tissue, is the tissue which is mineralized and has a firm intercellular matrix. The hard tissues of humans are bone, tooth enamel, dentin, and cementum. The term is in contrast to soft tissue.

References

  1. ↑ Brunton, P.A.; Davies, R.P.W. (2 July 2013). "Treatment of early caries lesions using biomimetic self-assembling-peptides – a clinical safety trial". Br Dent J. 215 (E6): E6. doi:10.1038/sj.bdj.2013.741. PMC   3813405 . PMID   23969679.
  2. ↑ "European Commission database with information on cosmetic substances and ingredients". Oligopeptide 104. Retrieved 1 July 2015.
  3. ↑ Kirkham, J; et al. (May 2007). "Self-assembling Peptide Scaffolds Promote Enamel Remineralization". J Dent Res. 86 (5): 426–430. doi:10.1177/154405910708600507. PMID   17452562. S2CID   21582771.
  4. ↑ "credentis webpage" . Retrieved 1 July 2015.
  5. ↑ AG, Touch Design. "Credentis: credentis ag and Dr. Wild & Co. AG strengthen their successful partnership". www.credentis.com. Retrieved 2016-06-29.
  6. ↑ Aggeli, A; Bell, M; et al. (20 March 1997). "Responsive gels formed by the spontaneous self-assembly of peptides into polymeric β-sheet tapes". Nature. 386 (6622): 259–262. Bibcode:1997Natur.386..259A. doi:10.1038/386259a0. PMID   9069283. S2CID   4343341.
  7. ↑ Alkilzy, M; et al. (May 15, 2015). "Efficacy, Clinical Applicability and Safety, of CurodontTM Repair in Children with Early Occlusal Caries". Caries Res. 49: 311. doi:10.1159/000381323. S2CID   79016534.
  8. ↑ Chen, X; et al. (Sep 2014). "Dentine Tubule Occlusion of a Novel Self-n Vitro Evaluation of Dentine Remineralisation by a Self-Assembling Peptide Using Scanning Electron Microscopy". Caries Res. 48: 402. doi: 10.1159/000360836 . Retrieved 1 July 2015.
  9. ↑ "Candida Zahnpasta Protect Professional" . Retrieved 1 July 2015.
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