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R7752

Sigma-Aldrich

Ristomycin monosulfate

≥90% ristocetin A basis (balance primarily Ristocetin B), powder, platelet activator

Synonym(s):

Ristocetin sulfate salt

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About This Item

Empirical Formula (Hill Notation):
C95H110N8O44 · H2SO4
CAS Number:
11140-99-1
Molecular Weight:
2166.00
MDL number:
MFCD00076121
UNSPSC Code:
12352202
PubChem Substance ID:
24899399
NACRES:
NA.77

product name

Ristomycin monosulfate, ≥90% ristocetin A basis (balance primarily Ristocetin B)

Quality Level

200

assay

≥90% ristocetin A basis (balance primarily Ristocetin B)

mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

COC(=O)[C@@H]1NC(=O)[C@H]2NC(=O)C(NC(=O)[C@@H]3NC(=O)[C@H]4NC(=O)[C@H](NC(=O)[C@H](N)c5ccc(O)c(Oc6cc4cc(O)c6C)c5)[C@H](O)c7ccc(Oc8cc3cc(Oc9ccc(cc9)[C@H]2O[C@H]%10C[C@@H](N)[C@@H](O)[C@H](C)O%10)c8O[C@@H]%11O[C@H](CO[C@@H]%12O[C@@H](C)[C@H](O)[C@@H](O)[C@H]%12O)[C@@H](O)[C@H](O)[C@H]%11O[C@H]%13O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%13O[C@@H]%14OC[C@@H](O)[C@@H](O)[C@@H]%14O)cc7)c%15ccc(O)c(c%15)-c%16c(O[C@@H]%17O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%17O)cc(O)cc1%16

InChI

1S/C95H110N8O44/c1-30-47(109)18-37-20-49(30)139-50-19-35(9-16-46(50)108)59(97)84(125)102-64-68(113)33-5-11-40(12-6-33)137-52-21-38-22-53(81(52)145-95-83(76(121)72(117)56(143-95)29-134-91-78(123)73(118)67(112)32(3)136-91)147-94-82(75(120)71(116)55(27-105)142-94)146-92-77(122)69(114)48(110)28-133-92)138-41-13-7-34(8-14-41)80(144-57-25-44(96)66(111)31(2)135-57)65-89(130)101-63(90(131)132-4)43-23-39(106)24-51(140-93-79(124)74(119)70(115)54(26-104)141-93)58(43)42-17-36(10-15-45(42)107)60(85(126)103-65)98-87(128)62(38)99-86(127)61(37)100-88(64)129/h5-24,31-32,44,48,54-57,59-80,82-83,91-95,104-124H,25-29,96-97H2,1-4H3,(H,98,128)(H,99,127)(H,100,129)(H,101,130)(H,102,125)(H,103,126)/t31-,32-,44+,48+,54+,55+,56+,57-,59+,60?,61-,62+,63?,64+,65-,66-,67-,68+,69+,70+,71+,72+,73+,74-,75-,76-,77-,78+,79-,80+,82-,83+,91+,92-,93+,94+,95-/m0/s1

InChI key

VUOPFFVAZTUEGW-ZNAZZOOYSA-N

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General description

Ristomycin/ristocetin is a type III glycopeptide. It is a highly glycosylated glycopeptide, previously found in Amycolatopsis lurida.

Application

Ristomycin monosulfate has been used:
  • to activate platelet and induce platelet aggregation
  • to study the aggregation responses of platelets from buffalo, horse, pig and sheep
  • in in-house ristocetin cofactor von Willebrand factor (VWF:RCo) assay to measure glycoprotein Ib (GpIb) binding activity

Biochem/physiol Actions

Ristocetin activates platelets. Ristocetin-induced platelet agglutination (RIPA) is decreased in patients undergoing chronic hemodialysis. Together with increased plasma glycocalicin levels (a product of enzymatic cleavage of GPIb), RIPA may contribute to diminished platelet adhesion to vascular subendothelium and increased bleeding associated with uremia. Addition of ristocetin and vWf caused specific agglutination of rGPIbα-liposomes suporting the potential use of rGPIbα-liposomes to enhance platelet function in vivo and support hemostasis in thrombocytopenic individuals.
Ristomycin possesses antibacterial activity. It may be used to diagnose von Willebrand disease and Bernard-Soulier syndrome. Ristocetin-induced platelet agglutination (RIPA) is decreased in patients undergoing chronic hemodialysis. Increased plasma glycocalicin levels (a product of enzymatic cleavage of GPIb) and decreased RIPA might reduce platelet adhesion to vascular subendothelium and improve bleeding associated with uremia in patients with chronic hemodialysis.

Other Notes

Glycopeptide antibiotic complex

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bleeding Symptoms and von Willebrand Factor Levels: 30-Year Experience in a Tertiary Care Center
Moonla C, et al.
Clinical and Applied Thrombosis/Hemostasis : Official Journal of the International Academy of Clinical and Applied Thrombosis/Hemostasis (2019)
A Kasirer-Friede et al.
Thrombosis and haemostasis, 80(3), 428-436 (1998-10-06)
We recently reported that washed platelets (WP) activated with ADP and expressing surface-bound vWF aggregated in flow through small tubes or in a cylindrical couette device at physiological shear rates of G = 300 s(-1)-1000 s(-1) in the absence of
Elevated plasma glycocalicin levels and decreased ristocetin-induced platelet agglutination in hemodialysis patients
Himmelfarb J, et al.
American Journal of Kidney Diseases, 32(1), 132-138 (1998)
Jordan, D.C. et al.
Antibiotics, 1, 84-84 (1967)
Species variability in platelet aggregation response to different agonists
Pelagalli A, et al.
Journal of Comparative Pathology, 127(2-3), 126-132 (2019)
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