Kendomycin | CAS#183202-73-5 | endothelin receptor antagonist | proteasome inhibitor

MedKoo Cat#: 540256 | Name: Kendomycin

Description:

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

Kendomycin is an endothelin receptor antagonist and proteasome inhibitor. It induces apoptosis in lymphoma.

Chemical Structure

Kendomycin

CAS#183202-73-5

Theoretical Analysis

MedKoo Cat#: 540256

Name: Kendomycin

CAS#: 183202-73-5

Chemical Formula: C29H42O6

Exact Mass: 486.2981

Molecular Weight: 486.64

Elemental Analysis: C, 71.57; H, 8.70; O, 19.73

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Kendomycin; TAN 2162; TAN-2162; TAN2162

IUPAC/Chemical Name

N/A

InChi Key

HKLDUJXJTQJSEJ-XNTDXEJSSA-N

InChi Code

InChI=1S/C29H42O6/c1-14-8-9-22-18(5)24(30)19(6)28(34-22)23-21-13-29(33,17(4)12-16(3)11-15(2)10-14)35-27(21)20(7)25(31)26(23)32/h10,13-14,16-19,22,24,28,30,32-33H,8-9,11-12H2,1-7H3/b15-10+

SMILES Code

CC1CCC2C(C)C(O)C(C)C(C3=C(O)C(C(C)=C4C3=CC(C(C)CC(C)C/C(C)=C/1)(O)O4)=O)O2

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

>2 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 486.64 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: Tanaka K, Matsuyama H, Watanabe M, Fujimori Y, Ishibashi K, Ozawa T, Sato T, Saikawa Y, Nakata M. Synthesis and biological evaluation of kendomycin and its analogues. J Org Chem. 2014 Nov 7;79(21):9922-47. doi: 10.1021/jo5015273. Epub 2014 Aug 26. PubMed PMID: 25136928. 2: Sengoku T, Xu S, Ogura K, Emori Y, Kitada K, Uemura D, Arimoto H. Total synthesis of the antibiotic kendomycin: a macrocyclization using the Tsuji-Trost etherification. Angew Chem Int Ed Engl. 2014 Apr 14;53(16):4213-6. doi: 10.1002/anie.201400305. Epub 2014 Mar 12. PubMed PMID: 24623596. 3: Elnakady YA, Chatterjee I, Bischoff M, Rohde M, Josten M, Sahl HG, Herrmann M, Müller R. Investigations to the Antibacterial Mechanism of Action of Kendomycin. PLoS One. 2016 Jan 21;11(1):e0146165. doi: 10.1371/journal.pone.0146165. eCollection 2016. PubMed PMID: 26795276; PubMed Central PMCID: PMC4721675. 4: Beck P, Heinemeyer W, Späth AL, Elnakady Y, Müller R, Groll M. Interactions of the natural product kendomycin and the 20S proteasome. J Mol Biol. 2014 Sep 9;426(18):3108-17. doi: 10.1016/j.jmb.2014.06.019. Epub 2014 Jul 16. PubMed PMID: 25038530. 5: Hoffmeister L, Persich P, Fürstner A. Formal total synthesis of kendomycin by way of alkyne metathesis/gold catalysis. Chemistry. 2014 Apr 7;20(15):4396-402. doi: 10.1002/chem.201304580. Epub 2014 Mar 3. PubMed PMID: 24591211. 6: Elnakady YA, Rohde M, Sasse F, Backes C, Keller A, Lenhof HP, Weissman KJ, Müller R. Evidence for the mode of action of the highly cytotoxic Streptomyces polyketide kendomycin. Chembiochem. 2007 Jul 23;8(11):1261-72. PubMed PMID: 17592829. 7: Tanaka K, Watanabe M, Ishibashi K, Matsuyama H, Saikawa Y, Nakata M. Total synthesis of kendomycin featuring intramolecular Dötz benzannulation. Org Lett. 2010 Apr 16;12(8):1700-3. doi: 10.1021/ol100229f. PubMed PMID: 20225835. 8: Xu S, Arimoto H. Strategies for construction of the all-carbon macrocyclic skeleton of the ansamycin antibiotic-kendomycin. J Antibiot (Tokyo). 2016 Apr;69(4):203-12. doi: 10.1038/ja.2016.5. Epub 2016 Feb 10. Review. PubMed PMID: 26860467. 9: Bahnck KB, Rychnovsky SD. Formal synthesis of (-)-kendomycin featuring a Prins-cyclization to construct the macrocycle. J Am Chem Soc. 2008 Oct 1;130(39):13177-81. doi: 10.1021/ja805187p. Epub 2008 Sep 4. PubMed PMID: 18767844; PubMed Central PMCID: PMC2697922. 10: Martin HJ, Magauer T, Mulzer J. In pursuit of a competitive target: total synthesis of the antibiotic kendomycin. Angew Chem Int Ed Engl. 2010 Aug 2;49(33):5614-26. doi: 10.1002/anie.201000227. Review. PubMed PMID: 20818753. 11: Pichlmair S, Marques MM, Green MP, Martin HJ, Mulzer J. A novel approach toward the synthesis of kendomycin: selective synthesis of a C-aryl glycoside as a single atropisomer. Org Lett. 2003 Nov 27;5(24):4657-9. PubMed PMID: 14627408. 12: Green MP, Pichlmair S, Marques MM, Martin HJ, Diwald O, Berger T, Mulzer J. Synthesis of analogue structures of the p-quinone methide moiety of kendomycin. Org Lett. 2004 Sep 2;6(18):3131-4. PubMed PMID: 15330605. 13: Janssen CO, Lim S, Lo EP, Wan KF, Yu VC, Lee MA, Ng SB, Everett MJ, Buss AD, Lane DP, Boyce RS. Interaction of kendomycin and semi-synthetic analogues with the anti-apoptotic protein Bcl-xl. Bioorg Med Chem Lett. 2008 Nov 1;18(21):5771-3. doi: 10.1016/j.bmcl.2008.09.071. Epub 2008 Sep 23. PubMed PMID: 18845435. 14: Wenzel SC, Bode HB, Kochems I, Müller R. A type I/type III polyketide synthase hybrid biosynthetic pathway for the structurally unique ansa compound kendomycin. Chembiochem. 2008 Nov 3;9(16):2711-21. doi: 10.1002/cbic.200800456. PubMed PMID: 18972512. 15: Williams DR, Shamim K. Efforts toward the total synthesis of (-)-kendomycin. Org Lett. 2005 Sep 15;7(19):4161-4. PubMed PMID: 16146377. 16: Magauer T, Martin HJ, Mulzer J. Total synthesis of the antibiotic kendomycin by macrocyclization using photo-Fries rearrangement and ring-closing metathesis. Angew Chem Int Ed Engl. 2009;48(33):6032-6. doi: 10.1002/anie.200900522. PubMed PMID: 19350596. 17: Lowe JT, Panek JS. Total synthesis of (-)-kendomycin. Org Lett. 2008 Sep 4;10(17):3813-6. doi: 10.1021/ol801499s. Epub 2008 Aug 13. PubMed PMID: 18698784. 18: Smith AB 3rd, Mesaros EF, Meyer EA. Total synthesis of (-)-kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis synthetic strategy. J Am Chem Soc. 2005 May 18;127(19):6948-9. PubMed PMID: 15884927. 19: Yuan Y, Men H, Lee C. Total synthesis of kendomycin: a macro-C-glycosidation approach. J Am Chem Soc. 2004 Nov 17;126(45):14720-1. PubMed PMID: 15535687; PubMed Central PMCID: PMC1785127. 20: Mulzer J, Pichlmair S, Green MP, Marques MM, Martin HJ. Toward the synthesis of the carbacylic ansa antibiotic kendomycin. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):11980-5. Epub 2004 Jul 26. PubMed PMID: 15277689; PubMed Central PMCID: PMC514420.