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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H13O9P
Molecular Weight 260.1358
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MANNOSE 6-PHOSPHATE

SMILES

O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H](O)C=O

InChI

InChIKey=VFRROHXSMXFLSN-KVTDHHQDSA-N
InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h1,3-6,8-11H,2H2,(H2,12,13,14)/t3-,4-,5-,6-/m1/s1

HIDE SMILES / InChI

Molecular Formula C6H13O9P
Molecular Weight 260.1358
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Mannose 6-phosphate (M6P) has type-I integral membrane receptors. M6P-receptors bind and transport M6P-enzymes to lysosomes, but it can also modulate the activity of a variety of extracellular M6P-glycoproteins (i.e., latent TGFbeta precursor, urokinase-type plasminogen activator receptor, Granzyme B, growth factors, Herpes virus). M6P has been demonstrated to reduce active TGF-β1 expression on cultured tendon fibroblasts and improved range of movement in a rabbit flexor tendon injury model. Studies of M6P in relation to skin scarring demonstrate improvement in scar cosmesis and accelerated return of normal dermal architecture. Juvidex, a formulation of M6P, inhibits the activation of TGF-beta1 and TGF-beta2, which are present at high levels in adult wounds that scar. On the other hands, M6P in a 600 mM hypertonic solution (Adaprev) potentially acts via a physical, non-chemical, hyperosmotic effect.

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
100µL of 300 mM (8.46 mg/100μL) or 600 mM (16.93 mg/100μL) Juvidex will be injected intradermally into each cm2 of one 3cm2 donor site and into the 0.5cm border around the donor site no more than 20 minutes before graft harvest (total dose 750µL). A further 300µL of 300mM (8.46 mg/100μL) Juvidex will be applied topically within 30 minutes of graft harvest and 24 hours after graft harvest.
Route of Administration: Other
In Vitro Use Guide
Tendon fibroblasts in culture developed a spindle shaped morphology in culture but once exposed to increasing doses of mannose 6-phosphate developed increasingly rounder morphologies with all cells viable. The number of completely rounded cells was quantified (no cytoplasmic protrusions) and shown to present mostly in the 600 mM mannose 6-phosphate treated group at increasing numbers the longer the cells were exposed.
Substance Class Chemical
Record UNII
U2S53JF879
Record Status Validated (UNII)
Record Version