Hyaluronic acid

Hyaluronic acid

Haworth projection
Names
IUPAC name
(1→4)-(2-Acetamido-2-deoxy-D-gluco)-(1→3)-D-glucuronoglycan
Systematic IUPAC name
Poly{[(2S,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxane-2,4-diyl]oxy[(2R,3R,4R,5S,6S)-6-carboxy-3,4-dihydroxyoxane-2,5-diyl]oxy}
Identifiers
ChEBI
ChemSpider
  • None
ECHA InfoCard 100.029.695 Edit this at Wikidata
EC Number
  • 232-678-0
UNII
Properties
(C14H21NO11)n
Pharmacology
D03AX05 (WHO) M09AX01 (WHO), R01AX09 (WHO), S01KA01 (WHO)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hyaluronic acid (/ˌhaɪ.əljʊəˈrɒnɪk/;[1][2] abbreviated HA; conjugate base hyaluronate), also called hyaluronan, is an anionic, nonsulfated glycosaminoglycan distributed widely throughout connective, epithelial, and neural tissues. It is unique among glycosaminoglycans as it is non-sulfated, forms in the plasma membrane instead of the Golgi apparatus, and can be very large: human synovial HA averages about 7 MDa per molecule, or about 20,000 disaccharide monomers,[3] while other sources mention 3–4 MDa.[4]

Medically, hyaluronic acid is used to treat osteoarthritis of the knee, dry eye, for wound repair, and as a cosmetic filler.[5]

The average 70 kg (150 lb) person has roughly 15 grams of hyaluronan in the body, one third of which is turned over (i.e., degraded and synthesized) per day.[6]

As one of the chief components of the extracellular matrix, it contributes significantly to cell proliferation and migration, and is involved in the progression of many malignant tumors.[7][8] Hyaluronic acid is also a component of the group A streptococcal extracellular capsule,[9] and is believed to play a role in virulence.[10][11][12]

  1. ^ "Hyaluronic Acid | Definition of Hyaluronic Acid by Oxford Dictionary". Lexico Dictionaries | English. Archived from the original on October 6, 2019.
  2. ^ "Hyaluronic acid". wordreference.com.
  3. ^ Fraser JR, Laurent TC, Laurent UB (1997). "Hyaluronan: its nature, distribution, functions and turnover". J. Intern. Med. 242 (1): 27–33. doi:10.1046/j.1365-2796.1997.00170.x. PMID 9260563. S2CID 37551992.
  4. ^ Cite error: The named reference Saari-1993 was invoked but never defined (see the help page).
  5. ^ Exploring the Medical Value of Hyaluronic Acid (HA), Stanford Chemicals Company
  6. ^ Stern R (2004). "Hyaluronan catabolism: a new metabolic pathway". Eur. J. Cell Biol. 83 (7): 317–25. doi:10.1078/0171-9335-00392. PMID 15503855.
  7. ^ Stern, Robert, ed. (2009). Hyaluronan in cancer biology (1st ed.). San Diego, CA: Academic Press/Elsevier. ISBN 978-0-12-374178-3.
  8. ^ Itano, Naoki (2002). "Abnormal accumulation of hyaluronan matrix diminishes contact inhibition of cell growth and promotes cell migration". Proceedings of the National Academy of Sciences. 99 (6). Proc Natl Acad Sci USA: 3609–3614. Bibcode:2002PNAS...99.3609I. doi:10.1073/pnas.052026799. PMC 122571. PMID 11891291.
  9. ^ Sugahara K, Schwartz NB, Dorfman A (1979). "Biosynthesis of hyaluronic acid by Streptococcus" (PDF). J. Biol. Chem. 254 (14): 6252–6261. doi:10.1016/S0021-9258(18)50356-2. PMID 376529.
  10. ^ Rao S, Pham TH, Poudyal S, Cheng LW, Nazareth SC, Wang PC, et al. (2021-04-27). "First report on genetic characterization, cell-surface properties and pathogenicity of Lactococcus garvieae, emerging pathogen isolated from cage-cultured cobia (Rachycentron canadum)". Transboundary and Emerging Diseases. 69 (3). Hindawi Limited: 1197–1211. doi:10.1111/tbed.14083. ISSN 1865-1674. PMID 33759359. S2CID 232338928.
  11. ^ Wessels MR, Moses AE, Goldberg JB, DiCesare TJ (1991). "Hyaluronic acid capsule is a virulence factor for mucoid group A streptococci". Proc. Natl. Acad. Sci. U.S.A. 88 (19): 8317–8321. Bibcode:1991PNAS...88.8317W. doi:10.1073/pnas.88.19.8317. PMC 52499. PMID 1656437.
  12. ^ Schrager HM, Rheinwald JG, Wessels MR (1996). "Hyaluronic acid capsule and the role of streptococcal entry into keratinocytes in invasive skin infection". J. Clin. Invest. 98 (9): 1954–1958. doi:10.1172/JCI118998. PMC 507637. PMID 8903312.