PF 1022A
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Hodoodo CAT#: H585005

CAS#: 133413-70-4

Description: PF 1022A is an anthelmintic depsipeptide isolated from Mycelia Sterilia.

Chemical Structure

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PF 1022A
CAS# 133413-70-4
Instruction

Theoretical Analysis

Hodoodo Cat#: H585005
Name: PF 1022A
CAS#: 133413-70-4
Chemical Formula: C52H76N4O12
Exact Mass: 948.55
Molecular Weight: 949.196
Elemental Analysis: C, 65.80; H, 8.07; N, 5.90; O, 20.23

Price and Availability

Size Price Availability Quantity
1mg USD 280 2 Weeks
5mg USD 850 2 Weeks
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Synonym: PF 1022A; PF1022A; PF-1022A

IUPAC/Chemical Name: (3S,6R,9S,12R,15S,18R,21S,24R)-6,18-Dibenzyl-3,9,15,21-tetraisobutyl-4,10,12,16,22,24-hexamethyl-1,7,13,19-tetraoxa-4,10,16,22-tetraazacyclo-tetracosane-2,5,8,11,14,17,20,23-octaone

InChi Key: YJNUXGPXJFAUQJ-LYWANRAQSA-N

InChi Code: InChI=1S/C52H76N4O12/c1-31(2)25-39-49(61)65-35(9)45(57)53(11)42(28-34(7)8)52(64)68-44(30-38-23-19-16-20-24-38)48(60)56(14)40(26-32(3)4)50(62)66-36(10)46(58)54(12)41(27-33(5)6)51(63)67-43(47(59)55(39)13)29-37-21-17-15-18-22-37/h15-24,31-36,39-44H,25-30H2,1-14H3/t35-,36-,39+,40+,41+,42+,43-,44-/m1/s1

SMILES Code: O=C([C@H](CC(C)C)N(C)C([C@@H](CC1=CC=CC=C1)OC([C@H](CC(C)C)N(C)C([C@@H](C)OC([C@H](CC(C)C)N(C)C([C@@H](CC2=CC=CC=C2)OC([C@H](CC(C)C)N3C)=O)=O)=O)=O)=O)=O)O[C@H](C)C3=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: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 949.20 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Zahner H, Taubert A, Harder A, von Samson-Himmelstjerna G. Filaricidal efficacy of anthelmintically active cyclodepsipeptides. Int J Parasitol. 2001 Nov;31(13):1515-22. PubMed PMID: 11595239.

2: von Samson-Himmelstjerna G, Harder A, Schnieder T, Kalbe J, Mencke N. In vivo activities of the new anthelmintic depsipeptide PF 1022A. Parasitol Res. 2000 Mar;86(3):194-9. PubMed PMID: 10726989.

3: Sivanathan S, Körber F, Scherkenbeck J. Semisynthetic routes to PF1022H--A precursor for new derivatives of the anthelmintic cyclooctadepsipeptide PF1022A. Bioorg Med Chem. 2016 Feb 15;24(4):873-6. doi: 10.1016/j.bmc.2016.01.014. Epub 2016 Jan 8. PubMed PMID: 26810834.

4: Jeschke P, Harder A, von Samson-Himmelstjerna G, Etzel W, Gau W, Thielking G, Bonse G. Synthesis of anthelmintically active N-methylated amidoxime analogues of the cyclic octadepsipeptide PF1022A. Pest Manag Sci. 2002 Dec;58(12):1205-15. PubMed PMID: 12476993.

5: Harder A, Schmitt-Wrede HP, Krücken J, Marinovski P, Wunderlich F, Willson J, Amliwala K, Holden-Dye L, Walker R. Cyclooctadepsipeptides--an anthelmintically active class of compounds exhibiting a novel mode of action. Int J Antimicrob Agents. 2003 Sep;22(3):318-31. Review. PubMed PMID: 13678839.

6: Kulke D, Krücken J, Harder A, Krebber R, Fraatz K, Mehlhorn H, VON Samson-Himmelstjerna G. In vivo efficacy of PF1022A and nicotinic acetylcholine receptor agonists alone and in combination against Nippostrongylus brasiliensis. Parasitology. 2013 Sep;140(10):1252-65. doi: 10.1017/S0031182013000632. Epub 2013 Jun 7. PubMed PMID: 23742764.

7: Geary TG, Sangster NC, Thompson DP. Frontiers in anthelmintic pharmacology. Vet Parasitol. 1999 Aug 1;84(3-4):275-95. Review. PubMed PMID: 10456419.

8: Krücken J, Harder A, Jeschke P, Holden-Dye L, O'Connor V, Welz C, von Samson-Himmelstjerna G. Anthelmintic cyclcooctadepsipeptides: complex in structure and mode of action. Trends Parasitol. 2012 Sep;28(9):385-94. doi: 10.1016/j.pt.2012.06.005. Epub 2012 Jul 31. Review. PubMed PMID: 22858281.

9: Ohyama M, Okada Y, Takahashi M, Sakanaka O, Matsumoto M, Atsumi K. Structure-activity relationship of anthelmintic cyclooctadepsipeptides. Biosci Biotechnol Biochem. 2011;75(7):1354-63. Epub 2011 Jul 7. PubMed PMID: 21737929.

10: Scherkenbeck J, Jeschke P, Harder A. PF1022A and related cyclodepsipeptides - a novel class of anthelmintics. Curr Top Med Chem. 2002 Jul;2(7):759-77. Review. PubMed PMID: 12052189.

11: Harder A, von Samson-Himmelstjerna G. Cyclooctadepsipeptides--a new class of anthelmintically active compounds. Parasitol Res. 2002 Jun;88(6):481-8. Epub 2002 Mar 16. Review. PubMed PMID: 12107468.

12: Kachi S, Terada M, Hashimoto H. Effects of amorphous and polymorphs of PF1022A, a new antinematode drug, on Angiostrongylus costaricensis in mice. Jpn J Pharmacol. 1998 Jul;77(3):235-45. PubMed PMID: 9717771.

13: Lee BH, Dutton FE, Thompson DP, Thomas EM. Generation of a small library of cyclodepsipeptide PF1022A analogues using a cyclization-cleavage method with oxime resin. Bioorg Med Chem Lett. 2002 Feb 11;12(3):353-6. PubMed PMID: 11814795.

14: Jeschke R, Iinuma K, Harder A, Schindler M, Murakami T. Influence of the cyclooctadepsipeptides PF1022A and PF1022E as natural products on the design of semi-synthetic anthelmintics such as emodepside. Parasitol Res. 2005 Oct;97 Suppl 1:S11-S16. doi: 10.1007/s00436-005-1439-y. PubMed PMID: 16228266.

15: Sasaki T, Takagi M, Yaguchi T, Miyadoh S, Okada T, Koyama M. A new anthelmintic cyclodepsipeptide, PF1022A. J Antibiot (Tokyo). 1992 May;45(5):692-7. Erratum in: J Antibiot (Tokyo) 1996 Sep;49(9):C-2. PubMed PMID: 1624372.

16: Weckwerth W, Miyamoto K, Iinuma K, Krause M, Glinski M, Storm T, Bonse G, Kleinkauf H, Zocher R. Biosynthesis of PF1022A and related cyclooctadepsipeptides. J Biol Chem. 2000 Jun 9;275(23):17909-15. PubMed PMID: 10751395.

17: Dutton FE, Nelson SJ. Synthesis of PF1022A, an anthelmintic cyclodepsipeptide. J Antibiot (Tokyo). 1994 Nov;47(11):1322-7. PubMed PMID: 8002397.

18: Yanai K, Sumida N, Okakura K, Moriya T, Watanabe M, Murakami T. Para-position derivatives of fungal anthelmintic cyclodepsipeptides engineered with Streptomyces venezuelae antibiotic biosynthetic genes. Nat Biotechnol. 2004 Jul;22(7):848-55. Epub 2004 Jun 6. PubMed PMID: 15184904.

19: Conder GA, Johnson SS, Nowakowski DS, Blake TE, Dutton FE, Nelson SJ, Thomas EM, Davis JP, Thompson DP. Anthelmintic profile of the cyclodepsipeptide PF1022A in in vitro and in vivo models. J Antibiot (Tokyo). 1995 Aug;48(8):820-3. Erratum in: J Antibiot (Tokyo) 1995 Nov;48(11):C-2. PubMed PMID: 7592027.

20: Dyker H, Scherkenbeck J, Gondol D, Goehrt A, Harder A. Azadepsipeptides: synthesis and evaluation of a novel class of peptidomimetics. J Org Chem. 2001 Jun 1;66(11):3760-6. PubMed PMID: 11374995.