Rhizopodin | CAS#150346-23-9 | macrolide antibiotic

MedKoo Cat#: 461310 | Name: Rhizopodin

Description:

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

Rhizopodin is a natural compound that strongly affects the actin cytoskeleton at nanomolar concentrations. It is used as a potent macrolide antibiotic.

Chemical Structure

Rhizopodin

CAS#150346-23-9

Theoretical Analysis

MedKoo Cat#: 461310

Name: Rhizopodin

CAS#: 150346-23-9

Chemical Formula: C39H62N2O11

Exact Mass: 734.4354

Molecular Weight: 734.92

Elemental Analysis: C, 63.74; H, 8.50; N, 3.81; O, 23.95

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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Related CAS #

No Data

Synonym

Rhizopodin;

IUPAC/Chemical Name

N-((E)-11-((12Z,12Z,14Z)-3,9-dihydroxy-11,17-dimethoxy-4,4-dimethyl-7-oxo-6-oxa-1(2,4)-oxazolacycloheptadecaphane-12,14-dien-5-yl)-4,10-dimethoxy-5,9-dimethyl-6-oxoundec-1-en-1-yl)-N-methylformamide

InChi Key

RAJHHZKPZIVDFF-OKKIHLRPSA-N

InChi Code

InChI=1S/C39H62N2O11/c1-26(17-18-31(44)27(2)32(48-7)16-13-19-41(5)25-42)34(50-9)22-36-39(3,4)35(45)23-37-40-30(24-51-37)33(49-8)15-12-10-11-14-29(47-6)20-28(43)21-38(46)52-36/h10-14,19,24-29,32-36,43,45H,15-18,20-23H2,1-9H3/b12-10-,14-11-,19-13+

SMILES Code

O=CN(/C=C/CC(OC)C(C)C(CCC(C)C(OC)CC(OC(CC(O)CC(OC)/C=C\C=C/CC1OC)=O)C(C)(C)C(O)CC2=NC1=CO2)=O)C

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 734.92 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.

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: Zhang S, Menche D, Zahler S, Vollmar AM, Liebl J, Förster F. In vitro anti-cancer effects of the actin-binding natural compound rhizopodin. Pharmazie. 2015 Sep;70(9):610-5. PubMed PMID: 26492647. 2: Dalby SM, Goodwin-Tindall J, Paterson I. Total synthesis of (-)-rhizopodin. Angew Chem Int Ed Engl. 2013 Jun 17;52(25):6517-21. doi: 10.1002/anie.201301978. Epub 2013 May 6. PubMed PMID: 23650089. 3: Pulukuri KK, Chakraborty TK. Formal synthesis of actin binding macrolide rhizopodin. Org Lett. 2014 Apr 18;16(8):2284-7. doi: 10.1021/ol5008179. Epub 2014 Apr 10. PubMed PMID: 24742162. 4: Oku N, Matsumoto A, Matsunaga T, Asano Y, Kasai H, Matoba S, Igarashi Y. Two new ring-contracted congeners of rhizopodin illustrate significance of the ring moiety of macrolide toxins on the actin disassembly-mediated cytotoxicity. Chem Pharm Bull (Tokyo). 2014;62(3):294-300. PubMed PMID: 24583785. 5: Herkommer D, Dreisigacker S, Sergeev G, Sasse F, Gohlke H, Menche D. Design, synthesis, and biological evaluation of simplified side chain hybrids of the potent actin binding polyketides rhizopodin and bistramide. ChemMedChem. 2015 Mar;10(3):470-89. doi: 10.1002/cmdc.201402508. Epub 2015 Jan 29. PubMed PMID: 25641798. 6: Melillo B, Chen MZ, Forestieri R, Smith AB 3rd. An Effective Bifunctional Aldehyde Linchpin for Type II Anion Relay Chemistry: Development and Application to the Synthesis of a C16-C29 Fragment of Rhizopodin. Org Lett. 2015 Dec 18;17(24):6242-5. doi: 10.1021/acs.orglett.5b03235. Epub 2015 Dec 7. PubMed PMID: 26641664; PubMed Central PMCID: PMC4720133. 7: Song L, Liu J, Gui H, Hui C, Zhou J, Guo Y, Zhang P, Xu Z, Ye T. Synthesis of the macrocyclic core of rhizopodin. Chem Asian J. 2013 Dec;8(12):2955-9. doi: 10.1002/asia.201300802. Epub 2013 Aug 22. PubMed PMID: 24038898. 8: Bender T, Loits D, White JM, Rizzacasa MA. Synthesis of the C1-C18 fragment of rhizopodin: late-state introduction of the oxazole. Org Lett. 2014 Mar 7;16(5):1450-3. doi: 10.1021/ol500261n. Epub 2014 Feb 13. PubMed PMID: 24524264. 9: Kretschmer M, Dieckmann M, Li P, Rudolph S, Herkommer D, Troendlin J, Menche D. Modular total synthesis of rhizopodin: a highly potent G-actin dimerizing macrolide. Chemistry. 2013 Nov 18;19(47):15993-6018. doi: 10.1002/chem.201302197. Epub 2013 Oct 10. PubMed PMID: 24123414. 10: Dieckmann M, Kretschmer M, Li P, Rudolph S, Herkommer D, Menche D. Total synthesis of rhizopodin. Angew Chem Int Ed Engl. 2012 Jun 4;51(23):5667-70. doi: 10.1002/anie.201201946. Epub 2012 Apr 24. PubMed PMID: 22532514. 11: Pistorius D, Müller R. Discovery of the rhizopodin biosynthetic gene cluster in Stigmatella aurantiaca Sg a15 by genome mining. Chembiochem. 2012 Feb 13;13(3):416-26. doi: 10.1002/cbic.201100575. Epub 2012 Jan 25. PubMed PMID: 22278953. 12: Gronewold TM, Sasse F, Lünsdorf H, Reichenbach H. Effects of rhizopodin and latrunculin B on the morphology and on the actin cytoskeleton of mammalian cells. Cell Tissue Res. 1999 Jan;295(1):121-9. PubMed PMID: 9931358. 13: Pulukuri KK, Chakraborty TK. Stereoselective synthesis of the monomeric unit of actin binding macrolide rhizopodin. Org Lett. 2012 Jun 1;14(11):2858-61. doi: 10.1021/ol301103d. Epub 2012 May 18. PubMed PMID: 22594399. 14: Kretschmer M, Menche D. Stereocontrolled synthesis of the C8-C22 fragment of rhizopodin. Org Lett. 2012 Jan 6;14(1):382-5. doi: 10.1021/ol203130b. Epub 2011 Dec 13. PubMed PMID: 22149453. 15: Dieckmann M, Rudolph S, Dreisigacker S, Menche D. Concise synthesis of the macrocyclic core of rhizopodin by a Heck macrocyclization strategy. J Org Chem. 2012 Dec 7;77(23):10782-8. doi: 10.1021/jo302134y. Epub 2012 Nov 26. PubMed PMID: 23157362. 16: Sasse F, Steinmetz H, Höfle G, Reichenbach H. Rhizopodin, a new compound from Myxococcus stipitatus (myxobacteria) causes formation of rhizopodia-like structures in animal cell cultures. Production, isolation, physico-chemical and biological properties. J Antibiot (Tokyo). 1993 May;46(5):741-8. PubMed PMID: 8514628. 17: Hagelueken G, Albrecht SC, Steinmetz H, Jansen R, Heinz DW, Kalesse M, Schubert WD. The absolute configuration of rhizopodin and its inhibition of actin polymerization by dimerization. Angew Chem Int Ed Engl. 2009;48(3):595-8. doi: 10.1002/anie.200802915. PubMed PMID: 19035596. 18: Horstmann N, Menche D. Configurational assignment of rhizopodin, an actin-binding macrolide from the myxobacterium Myxococcus stipitatus. Chem Commun (Camb). 2008 Nov 7;(41):5173-5. doi: 10.1039/b810405k. Epub 2008 Sep 9. PubMed PMID: 18956059. 19: Chen Z, Song L, Xu Z, Ye T. Synthesis of the C9-C23 (C9'-C23') fragment of the dimeric natural product rhizopodin. Org Lett. 2010 May 7;12(9):2036-9. doi: 10.1021/ol100515m. PubMed PMID: 20380407. 20: Nicolaou KC, Jiang X, Lindsay-Scott PJ, Corbu A, Yamashiro S, Bacconi A, Fowler VM. Total synthesis and biological evaluation of monorhizopodin and 16-epi-monorhizopodin. Angew Chem Int Ed Engl. 2011 Feb 1;50(5):1139-44. doi: 10.1002/anie.201006780. Epub 2011 Jan 7. PubMed PMID: 21268213; PubMed Central PMCID: PMC3139707.