RA VII | CAS#86229-97-2 | antitumor

MedKoo Cat#: 461108 | Name: RA VII

Description:

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

RA VII is an antitumor bicyclic hexapeptide of plant origin.

Chemical Structure

RA VII

CAS#86229-97-2

Theoretical Analysis

MedKoo Cat#: 461108

Name: RA VII

CAS#: 86229-97-2

Chemical Formula: C41H56N6O9

Exact Mass: 776.4109

Molecular Weight: 776.93

Elemental Analysis: C, 63.38; H, 7.27; N, 10.82; O, 18.53

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

RA VII; Methylether of TPC-A; RA-VII; RAVII;

IUPAC/Chemical Name

(11R,14S,17S,110S,113S,116S)-34-methoxy-110-(4-methoxybenzyl)-12,15,17,111,113,116-hexamethyl-4-oxa-12,15,18,111,114,117-hexaaza-1(1,4)-cyclooctadecana-3(1,3)-benzena-5(1,4)-cyclohexanacyclohexaphane-13,16,19,112,115,118-hexaone

InChi Key

NUIWKOKPWYJSOH-XKEKSGRPSA-N

InChi Code

InChI=1S/C41H56N6O9/c1-23-36(48)43-24(2)39(51)45(4)31(19-26-9-14-29(54-7)15-10-26)38(50)44-25(3)40(52)47(6)33-20-27-11-16-30(17-12-27)56-35-22-28(13-18-34(35)55-8)21-32(37(49)42-23)46(5)41(33)53/h9-10,13-15,18,22-25,27,30-33H,11-12,16-17,19-21H2,1-8H3,(H,42,49)(H,43,48)(H,44,50)/t23-,24-,25-,27?,30?,31-,32+,33-/m0/s1

SMILES Code

COc1ccc(C[C@@H]2N(C)C([C@H](C)NC([C@H](C)NC([C@@H]3N(C)C([C@@H](N(C)C([C@@H](NC2=O)C)=O)CC4CCC(Oc5cc(C3)ccc5OC)CC4)=O)=O)=O)=O)cc1

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 776.93 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: Hitotsuyanagi Y, Miyazawa A, Hinosawa TA, Nakagawa Y, Hasuda T, Takeya K. Aza-cycloisodityrosine analogue of RA-VII, an antitumor bicyclic hexapeptide. Bioorg Med Chem Lett. 2013 Dec 15;23(24):6728-31. doi: 10.1016/j.bmcl.2013.10.033. Epub 2013 Oct 26. PubMed PMID: 24268554. 2: Hasuda T, Hitotsuyanagi Y, Shinada M, Takeya K. Synthesis of [Tyr-5-Ψ(CH2NMe)-Tyr-6]RA-VII, a reduced peptide bond analogue of RA-VII, an antitumor bicyclic hexapeptide. Bioorg Med Chem Lett. 2012 Apr 15;22(8):2757-9. doi: 10.1016/j.bmcl.2012.02.093. Epub 2012 Mar 3. PubMed PMID: 22460024. 3: Hitotsuyanagi Y, Lee JE, Kato S, Kim IH, Kohashi H, Fukaya H, Takeya K. Per-N-methylated analogues of an antitumor bicyclic hexapeptide RA-VII. Bioorg Med Chem. 2011 Apr 1;19(7):2458-63. doi: 10.1016/j.bmc.2011.02.003. Epub 2011 Mar 5. PubMed PMID: 21382716. 4: Hasuda T, Hitotsuyanagi Y, Takeya K. Production of monoclonal antibodies against antitumor cyclohexapeptide RA-VII from Rubia cordifolia and their characterization. J Nat Med. 2011 Jul;65(3-4):588-93. doi: 10.1007/s11418-011-0508-z. Epub 2011 Feb 8. PubMed PMID: 21301980. 5: Hitotsuyanagi Y, Hasuda T, Aihara T, Ishikawa H, Yamaguchi K, Itokawa H, Takeya K. Synthesis of [Gly-1]RA-VII, [Gly-2]RA-VII, and [Gly-4]RA-VII. Glycine-containing analogues of RA-VII, an antitumor bicyclic hexapeptide from Rubia plants. J Org Chem. 2004 Mar 5;69(5):1481-6. PubMed PMID: 14987000. 6: Hitotsuyanagi Y, Odagiri M, Kato S, Kusano J, Hasuda T, Fukaya H, Takeya K. Isolation, structure determination, and synthesis of allo-RA-V and neo-RA-V, RA-series bicyclic peptides from Rubia cordifolia L. Chemistry. 2012 Mar 5;18(10):2839-46. doi: 10.1002/chem.201103185. Epub 2012 Feb 1. PubMed PMID: 22298232. 7: Wakita Ki, Minami M, Venkateswarlu A, Sharma VM, Ramesh M, Akahane K. Antitumor bicyclic hexapeptide RA-VII modulates cyclin D1 protein level. Anticancer Drugs. 2001 Jun;12(5):433-9. PubMed PMID: 11395571. 8: Fujiwara H, Saito SY, Hitotsuyanagi Y, Takeya K, Ohizumi Y. RA-VII, a cyclic depsipeptide, changes the conformational structure of actin to cause G2 arrest by the inhibition of cytokinesis. Cancer Lett. 2004 Jun 25;209(2):223-9. PubMed PMID: 15159025. 9: Koizumi T, Abe M, Yamakuni T, Ohizumi Y, Hitotsuyanagi Y, Takeya K, Sato Y. Metronomic scheduling of a cyclic hexapeptide Ra-VII for anti-angiogenesis, tumor vessel maturation and anti-tumor activity. Cancer Sci. 2006 Jul;97(7):665-74. PubMed PMID: 16827808. 10: Lee JE, Hitotsuyanagi Y, Nakagawa Y, Kato S, Fukaya H, Takeya K. Design and synthesis of a bis(cycloisodityrosine) analogue of RA-VII, an antitumor bicyclic hexapeptide. Bioorg Med Chem Lett. 2008 Dec 15;18(24):6458-61. doi: 10.1016/j.bmcl.2008.10.064. Epub 2008 Oct 18. PubMed PMID: 18993061. 11: Itokawa H, Takeya K, Mori N, Kidokoro S, Yamamoto H. Studies on antitumour cyclic hexapeptides RA obtained from Rubiae radix, Rubiaceae (IV): Quantitative determination of RA-VII and RA-V in commercial Rubiae radix and collected plants. Planta Med. 1984 Aug;50(4):313-6. PubMed PMID: 6505082. 12: Itokawa H, Saitou K, Morita H, Takeya K, Yamada K. Structures and conformations of metabolites of antitumor cyclic hexapeptides, RA-VII and RA-X. Chem Pharm Bull (Tokyo). 1992 Nov;40(11):2984-9. PubMed PMID: 1477912. 13: Itokawa H, Morita H, Takeya K. Solution forms of an antitumor cyclic hexapeptide, RA-VII in dimethyl sulfoxide-d6 from nuclear magnetic resonance studies. Chem Pharm Bull (Tokyo). 1992 Apr;40(4):1050-2. PubMed PMID: 1525934. 14: Xu WY, Zhao SM, Zeng GZ, He WJ, Xu HM, Tan NH. [Progress in the study of some important natural bioactive cyclopeptides]. Yao Xue Xue Bao. 2012 Mar;47(3):271-9. Review. Chinese. PubMed PMID: 22645749. 15: Hitotsuyanagi Y, Sasaki S, Matsumoto Y, Yamaguchi K, Itokawa H, Takeya K. Synthesis of [L-Ala-1]RA-VII, [D-Ala-2]RA-VII, and [D-Ala-4]RA-VII by epimerization of RA-VII, an antitumor bicyclic hexapeptide from Rubia plants, through oxazoles. J Am Chem Soc. 2003 Jun 18;125(24):7284-90. Erratum in: J Am Chem Soc. 2004 Aug 11;126(31):9873. PubMed PMID: 12797802. 16: Inoue T, Sasaki T, Takayanagi H, Harigaya Y, Hoshino O, Hara H, Inaba T. A Synthesis of D,L-N,N-Dimethylcycloisodityrosines: A Comment on the Stereochemistry of Previously Reported Intermediates Related to the Synthesis of RA-VII and Deoxybouvardin. J Org Chem. 1996 Jun 14;61(12):3936-3937. PubMed PMID: 11667261. 17: Lee JE, Hitotsuyanagi Y, Kim IH, Hasuda T, Takeya K. A novel bicyclic hexapeptide, RA-XVIII, from Rubia cordifolia: structure, semi-synthesis, and cytotoxicity. Bioorg Med Chem Lett. 2008 Jan 15;18(2):808-11. Epub 2007 Nov 17. PubMed PMID: 18078747. 18: Kato T, Suzumura Y, Takamoto S, Ota K. Antitumor activity and toxicity in mice of RA-700, a cyclic hexapeptide. Anticancer Res. 1987 May-Jun;7(3 Pt B):329-34. PubMed PMID: 3631886. 19: Boger DL, Zhou J. Key analogues of the tetrapeptide subunit of RA-VII and deoxybouvardin. Bioorg Med Chem. 1996 Oct;4(10):1597-603. PubMed PMID: 8931929. 20: Itokawa H, Takeya K, Mori N, Takanashi M, Yamamoto H, Sonobe T, Kidokoro S. Cell growth-inhibitory effects of derivatives of antitumor cyclic hexapeptide RA-V obtained from Rubiae radix (V). Gan. 1984 Oct;75(10):929-36. PubMed PMID: 6510638.