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MedKoo Cat#: 597970 | Name: Angiopeptin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Angiopeptin is a synthetic octapeptide analog of somatostatin; inhibits accelerated transplant atherosclerosis in rabbit heart arteries.

Chemical Structure

Angiopeptin
Angiopeptin
CAS#113294-82-9

Theoretical Analysis

MedKoo Cat#: 597970

Name: Angiopeptin

CAS#: 113294-82-9

Chemical Formula: C54H71N11O10S2

Exact Mass: 1097.4827

Molecular Weight: 1098.34

Elemental Analysis: C, 59.05; H, 6.52; N, 14.03; O, 14.57; S, 5.84

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Angiopeptin; Bim 23014 C; D-Nal-cys-tyr-trp-lys-val-cys-thr-NH2;
IUPAC/Chemical Name
(S)-6-amino-2-((R)-2-((S)-2-((R)-2-((R)-2-amino-3-(naphthalen-2-yl)propanamido)-3-mercaptopropanamido)-3-(4-hydroxyphenyl)propanamido)-3-(1H-indol-3-yl)propanamido)-N-((S)-1-(((R)-1-(((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)amino)-3-mercapto-1-oxopropan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide
InChi Key
UGVPPRZHXAMSJP-SCTWWAJVSA-N
InChi Code
InChI=1S/C54H71N11O10S2/c1-29(2)45(54(75)63-44(28-77)53(74)65-46(30(3)66)47(57)68)64-49(70)40(14-8-9-21-55)59-51(72)42(25-35-26-58-39-13-7-6-12-37(35)39)61-50(71)41(24-31-16-19-36(67)20-17-31)60-52(73)43(27-76)62-48(69)38(56)23-32-15-18-33-10-4-5-11-34(33)22-32/h4-7,10-13,15-20,22,26,29-30,38,40-46,58,66-67,76-77H,8-9,14,21,23-25,27-28,55-56H2,1-3H3,(H2,57,68)(H,59,72)(H,60,73)(H,61,71)(H,62,69)(H,63,75)(H,64,70)(H,65,74)/t30-,38-,40+,41+,42-,43+,44+,45+,46+/m1/s1
SMILES Code
C[C@@H](O)[C@@H](C(N)=O)NC([C@H](CS)NC([C@H](C(C)C)NC([C@H](CCCCN)NC([C@@H](CC1=CNC2=C1C=CC=C2)NC([C@H](CC3=CC=C(O)C=C3)NC([C@H](CS)NC([C@@H](CC4=CC=C5C=CC=CC5=C4)N)=O)=O)=O)=O)=O)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,098.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Meiser BM, Mueller M, Foegh M, Von Scheidt W, Reichart B. Short-term angiopeptin therapy and the incidence of graft vessel disease after heart transplantation. J Heart Lung Transplant. 2002 Dec;21(12):1264-73. PubMed PMID: 12490271. 2: Kwok OH, Chow WH, Law TC, Chiu A, Ng W, Lam WF, Hong MK, Popma JJ. First human experience with angiopeptin-eluting stent: a quantitative coronary angiography and three-dimensional intravascular ultrasound study. Catheter Cardiovasc Interv. 2005 Dec;66(4):541-6. PubMed PMID: 16208695. 3: Armstrong J, Gunn J, Arnold N, Malik N, Chan KH, Vick T, Stratford P, Cumberland DC, Holt CM. Angiopeptin-eluting stents: observations in human vessels and pig coronary arteries. J Invasive Cardiol. 2002 May;14(5):230-8. PubMed PMID: 11983942. 4: Sidney EJ, Hampl V, Nelson DP, Archer SL, Foegh ML, Cathapermal SS, Weir EK. The somatostatin analog angiopeptin does not reduce chronic hypoxic pulmonary hypertension in rats. Proc Soc Exp Biol Med. 1996 Oct;213(1):43-9. PubMed PMID: 8820822. 5: Lee JR, Yang JH, Kim EK, Seo JW. Effect of angiopeptin and aspirin on accelerated graft atherosclerosis in transplanted mouse heart. J Korean Med Sci. 1999 Dec;14(6):607-12. PubMed PMID: 10642937; PubMed Central PMCID: PMC3054440. 6: Light JT, Bellan JA, Chen IL, Longenecker LL, Murphy WA, Coy DH, Kadowitz PJ, McNamara DB. Angiopeptin enhances acetylcholine-induced relaxation and inhibits intimal hyperplasia after vascular injury. Am J Physiol. 1993 Oct;265(4 Pt 2):H1265-74. PubMed PMID: 7902005. 7: Alderton F, Lauder H, Feniuk W, Fan TP, Humphrey PP. Differential effects of somatostatin and angiopeptin on cell proliferation. Br J Pharmacol. 1998 May;124(2):323-30. PubMed PMID: 9641549; PubMed Central PMCID: PMC1565396. 8: Vargas R, Wroblewska B, Rego A, Cathapermal S, Ramwell PW. Angiopeptin inhibits thymidine incorporation by explants of porcine coronary arteries. J Cardiovasc Pharmacol. 1997 Feb;29(2):278-83. PubMed PMID: 9057079. 9: Eriksen UH, Amtorp O, Bagger JP, Emanuelsson H, Foegh M, Henningsen P, Saunamäki K, Schaeffer M, Thayssen P, Orskov H, et al. Randomized double-blind Scandinavian trial of angiopeptin versus placebo for the prevention of clinical events and restenosis after coronary balloon angioplasty. Am Heart J. 1995 Jul;130(1):1-8. PubMed PMID: 7611096. 10: Foegh ML. Angiopeptin: a treatment for accelerated myointimal hyperplasia? J Heart Lung Transplant. 1992 May-Jun;11(3 Pt 2):S28-31. PubMed PMID: 1352465. 11: Foegh ML, Ramwell PW. Angiopeptin: experimental and clinical studies of inhibition of myointimal proliferation. Kidney Int Suppl. 1995 Dec;52:S18-22. Review. PubMed PMID: 8587276. 12: Santoian ED, Schneider JE, Gravanis MB, Foegh M, Tarazona N, Cipolla GD, King SB 3rd. Angiopeptin inhibits intimal hyperplasia after angioplasty in porcine coronary arteries. Circulation. 1993 Jul;88(1):11-4. PubMed PMID: 8100489. 13: Howell MH, Adams MM, Wolfe MS, Foegh ML, Ramwell PW. Angiopeptin inhibition of myointimal hyperplasia after balloon angioplasty of large arteries in hypercholesterolaemic rabbits. Clin Sci (Lond). 1993 Aug;85(2):183-8. PubMed PMID: 8104753. 14: Eriksen UH, Amtorp O, Bagger JP, Emanuelsson H, Foegh M, Saunamäki KI, Schaeffer M, Thayssen P, Orskov H, Kuntz RE, Popma JJ. [Angiopeptin versus placebo for reductin of restenosis after PTCA treatment. A randomized, double-blind study]. Ugeskr Laeger. 1996 Nov 11;158(46):6605-8. Danish. PubMed PMID: 8966826. 15: Zhao Y, Foegh ML. Angiopeptin, a somatostatin analogue, inhibits rat coronary artery and aorta smooth muscle cell proliferation induced by the thromboxane A2 mimetic U46619. Prostaglandins. 1997 Nov;54(5):781-93. PubMed PMID: 9491208. 16: Hong MK, Kent KM, Tio FO, Foegh M, Kornowski R, Bramwell O, Cathapermal SS, Leon MB. Single-dose intramuscular administration of sustained-release Angiopeptin reduces neointimal hyperplasia in a porcine coronary in-stent restenosis model. Coron Artery Dis. 1997 Feb;8(2):101-4. PubMed PMID: 9211050. 17: Cathapermal SS, Foegh ML, Rau CS, Ramwell PW. Disposition and tissue distribution of angiopeptin in the rat. Drug Metab Dispos. 1991 Jul-Aug;19(4):735-9. PubMed PMID: 1680648. 18: Lundergan CF, Foegh ML, Ramwell PW. Peptide inhibition of myointimal proliferation by angiopeptin, a somatostatin analogue. J Am Coll Cardiol. 1991 May;17(6 Suppl B):132B-136B. Review. PubMed PMID: 1673136. 19: Foegh ML, Khirabadi BS, Chambers E, Amamoo S, Ramwell PW. Inhibition of coronary artery transplant atherosclerosis in rabbits with angiopeptin, an octapeptide. Atherosclerosis. 1989 Aug;78(2-3):229-36. PubMed PMID: 2571335. 20: Foegh ML, Asotra S, Conte JV, Howell M, Kagan E, Verma K, Ramwell PW. Early inhibition of myointimal proliferation by angiopeptin after balloon catheter injury in the rabbit. J Vasc Surg. 1994 Jun;19(6):1084-91. PubMed PMID: 7911163.