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MedKoo Cat#: 597854 | Name: Dolastatin 15

Description:

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

Dolastatin 15 is an apoptotic agent through Blc-2 phosphorylation.

Chemical Structure

Dolastatin 15
Dolastatin 15
CAS#123884-00-4

Theoretical Analysis

MedKoo Cat#: 597854

Name: Dolastatin 15

CAS#: 123884-00-4

Chemical Formula: C45H68N6O9

Exact Mass: 836.5048

Molecular Weight: 837.07

Elemental Analysis: C, 64.57; H, 8.19; N, 10.04; O, 17.20

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Synonym
Dolastatin 15; Dolastatin15; Dolastatin-15; Dolostatin 15; Dolostatin15; Dolostatin-15; NSC 617668; NSC-617668; NSC617668; DLS-15; DLS15; DLS 15
IUPAC/Chemical Name
(S)-1-((S)-2-benzyl-3-methoxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-3-methyl-1-oxobutan-2-yl N-dimethyl-L-valyl-L-valyl-N-methyl-L-valyl-L-prolyl-L-prolinate
InChi Key
LQKSHSFQQRCAFW-CCVNJFHASA-N
InChi Code
InChI=1S/C45H68N6O9/c1-26(2)36(46-40(53)37(27(3)4)47(9)10)42(55)48(11)38(28(5)6)43(56)49-22-16-20-31(49)41(54)50-23-17-21-32(50)45(58)60-39(29(7)8)44(57)51-33(34(59-12)25-35(51)52)24-30-18-14-13-15-19-30/h13-15,18-19,25-29,31-33,36-39H,16-17,20-24H2,1-12H3,(H,46,53)/t31-,32-,33-,36-,37-,38-,39-/m0/s1
SMILES Code
O=C(O[C@H](C(N1[C@@H](CC2=CC=CC=C2)C(OC)=CC1=O)=O)C(C)C)[C@H]3N(C([C@H]4N(C([C@H](C(C)C)N(C([C@H](C(C)C)NC([C@H](C(C)C)N(C)C)=O)=O)C)=O)CCC4)=O)CCC3
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Dolastatin 15 (DLS 15), a depsipeptide derived from Dolabella auricularia, is a potent antimitotic agent structurally related to the antitubulin agent Dolastatin 10.
In vitro activity:
This study demonstrates for the first time that dolastatin 15 induces cell cycle arrest at the G2/M phase followed by apoptosis in various human myeloma cell lines (RPMI8226, U266, and IM9), suggesting that it has effects on mitotic spindles. In addition, this study showed that dolastatin 15 induces apoptosis of myeloma cells via activation of both mitochondrial- and Fas (CD95)/Fas-L (CD95-L)-mediated pathways. Reference: Int J Oncol. 2007 Jun;30(6):1453-9. https://pubmed.ncbi.nlm.nih.gov/17487366/
In vivo activity:
Dolastatin 15 displayed an antivascularization effect in human endothelial cells and in zebrafish vhl mutants with activated Hif, thus signifying its clinical potential as a treatment for solid tumors with an angiogenic component. Reference: Chembiochem. 2020 Aug 17;21(16):2356-2366. https://pubmed.ncbi.nlm.nih.gov/32237262/

Preparing Stock Solutions

The following data is based on the product molecular weight 837.07 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:
1. Sato M, Sagawa M, Nakazato T, Ikeda Y, Kizaki M. A natural peptide, dolastatin 15, induces G2/M cell cycle arrest and apoptosis of human multiple myeloma cells. Int J Oncol. 2007 Jun;30(6):1453-9. PMID: 17487366. 2. Ali MA, Rosati R, Pettit GR, Kalemkerian GP. Dolastatin 15 induces apoptosis and BCL-2 phosphorylation in small cell lung cancer cell lines. Anticancer Res. 1998 Mar-Apr;18(2A):1021-6. PMID: 9615758. 3. Ratnayake R, Gunasekera SP, Ma JJ, Dang LH, Carney TJ, Paul VJ, Luesch H. Dolastatin 15 from a Marine Cyanobacterium Suppresses HIF-1α Mediated Cancer Cell Viability and Vascularization. Chembiochem. 2020 Aug 17;21(16):2356-2366. doi: 10.1002/cbic.202000180. Epub 2020 May 12. PMID: 32237262; PMCID: PMC7438311.
In vitro protocol:
1. Sato M, Sagawa M, Nakazato T, Ikeda Y, Kizaki M. A natural peptide, dolastatin 15, induces G2/M cell cycle arrest and apoptosis of human multiple myeloma cells. Int J Oncol. 2007 Jun;30(6):1453-9. PMID: 17487366. 2. Ali MA, Rosati R, Pettit GR, Kalemkerian GP. Dolastatin 15 induces apoptosis and BCL-2 phosphorylation in small cell lung cancer cell lines. Anticancer Res. 1998 Mar-Apr;18(2A):1021-6. PMID: 9615758.
In vivo protocol:
1. Ratnayake R, Gunasekera SP, Ma JJ, Dang LH, Carney TJ, Paul VJ, Luesch H. Dolastatin 15 from a Marine Cyanobacterium Suppresses HIF-1α Mediated Cancer Cell Viability and Vascularization. Chembiochem. 2020 Aug 17;21(16):2356-2366. doi: 10.1002/cbic.202000180. Epub 2020 May 12. PMID: 32237262; PMCID: PMC7438311.
1: Piplani H, Vaish V, Rana C, Sanyal SN. Up-regulation of p53 and mitochondrial signaling pathway in apoptosis by a combination of COX-2 inhibitor, Celecoxib and Dolastatin 15, a marine mollusk linear peptide in experimental colon carcinogenesis. Mol Carcinog. 2013 Nov;52(11):845-58. doi: 10.1002/mc.21925. Epub 2012 May 23. PubMed PMID: 22623379. 2: Lopus M. Mechanism of mitotic arrest induced by dolastatin 15 involves loss of tension across kinetochore pairs. Mol Cell Biochem. 2013 Oct;382(1-2):93-102. doi: 10.1007/s11010-013-1721-8. Epub 2013 Jun 7. PubMed PMID: 23744533. 3: Gianolio DA, Rouleau C, Bauta WE, Lovett D, Cantrell WR Jr, Recio A 3rd, Wolstenholme-Hogg P, Busch M, Pan P, Stefano JE, Kramer HM, Goebel J, Krumbholz RD, Roth S, Schmid SM, Teicher BA. Targeting HER2-positive cancer with dolastatin 15 derivatives conjugated to trastuzumab, novel antibody-drug conjugates. Cancer Chemother Pharmacol. 2012 Sep;70(3):439-49. doi: 10.1007/s00280-012-1925-8. Epub 2012 Jul 22. PubMed PMID: 22821053. 4: Steube KG, Grunicke D, Pietsch T, Gignac SM, Pettit GR, Drexler HG. Dolastatin 10 and dolastatin 15: effects of two natural peptides on growth and differentiation of leukemia cells. Leukemia. 1992 Oct;6(10):1048-53. PubMed PMID: 1405759. 5: Piplani H, Vaish V, Sanyal SN. Dolastatin 15, a mollusk linear peptide, and Celecoxib, a selective cyclooxygenase-2 inhibitor, prevent preneoplastic colonic lesions and induce apoptosis through inhibition of the regulatory transcription factor NF-κB and an inflammatory protein, iNOS. Eur J Cancer Prev. 2012 Nov;21(6):511-22. PubMed PMID: 22441428. 6: Cruz-Monserrate Z, Mullaney JT, Harran PG, Pettit GR, Hamel E. Dolastatin 15 binds in the vinca domain of tubulin as demonstrated by Hummel-Dreyer chromatography. Eur J Biochem. 2003 Sep;270(18):3822-8. PubMed PMID: 12950266. 7: Poncet J, Busquet M, Roux F, Pierré A, Atassi G, Jouin P. Synthesis and biological activity of chimeric structures derived from the cytotoxic natural compounds dolastatin 10 and dolastatin 15. J Med Chem. 1998 Apr 23;41(9):1524-30. PubMed PMID: 9554885. 8: Sato M, Sagawa M, Nakazato T, Ikeda Y, Kizaki M. A natural peptide, dolastatin 15, induces G2/M cell cycle arrest and apoptosis of human multiple myeloma cells. Int J Oncol. 2007 Jun;30(6):1453-9. PubMed PMID: 17487366. 9: Bai R, Friedman SJ, Pettit GR, Hamel E. Dolastatin 15, a potent antimitotic depsipeptide derived from Dolabella auricularia. Interaction with tubulin and effects of cellular microtubules. Biochem Pharmacol. 1992 Jun 23;43(12):2637-45. PubMed PMID: 1632820. 10: Ali MA, Rosati R, Pettit GR, Kalemkerian GP. Dolastatin 15 induces apoptosis and BCL-2 phosphorylation in small cell lung cancer cell lines. Anticancer Res. 1998 Mar-Apr;18(2A):1021-6. PubMed PMID: 9615758. 11: Bai R, Edler MC, Bonate PL, Copeland TD, Pettit GR, Ludueña RF, Hamel E. Intracellular activation and deactivation of tasidotin, an analog of dolastatin 15: correlation with cytotoxicity. Mol Pharmacol. 2009 Jan;75(1):218-26. doi: 10.1124/mol.108.051110. Epub 2008 Oct 16. PubMed PMID: 18927208; PubMed Central PMCID: PMC2635573. 12: Schmitt J, Bernd M, Kutscher B, Kessler H. Synthesis of Dolastatin 15 mimetic peptoids. Bioorg Med Chem Lett. 1998 Feb 17;8(4):385-8. PubMed PMID: 9871690. 13: Piplani H, Rana C, Vaish V, Vaiphei K, Sanyal SN. Dolastatin, along with Celecoxib, stimulates apoptosis by a mechanism involving oxidative stress, membrane potential change and PI3-K/AKT pathway down regulation. Biochim Biophys Acta. 2013 Nov;1830(11):5142-56. doi: 10.1016/j.bbagen.2013.07.011. Epub 2013 Jul 18. PubMed PMID: 23872169. 14: Marks RS, Graham DL, Sloan JA, Hillman S, Fishkoff S, Krook JE, Okuno SH, Mailliard JA, Fitch TR, Addo F. A phase II study of the dolastatin 15 analogue LU 103793 in the treatment of advanced non-small-cell lung cancer. Am J Clin Oncol. 2003 Aug;26(4):336-7. PubMed PMID: 12902880. 15: Pettit GR, Flahive EJ, Boyd MR, Bai R, Hamel E, Pettit RK, Schmidt JM. Antineoplastic agents 360. Synthesis and cancer cell growth inhibitory studies of dolastatin 15 structural modifications. Anticancer Drug Des. 1998 Jan;13(1):47-66. PubMed PMID: 9474242. 16: Ebbinghaus S, Rubin E, Hersh E, Cranmer LD, Bonate PL, Fram RJ, Jekunen A, Weitman S, Hammond LA. A phase I study of the dolastatin-15 analogue tasidotin (ILX651) administered intravenously daily for 5 consecutive days every 3 weeks in patients with advanced solid tumors. Clin Cancer Res. 2005 Nov 1;11(21):7807-16. PubMed PMID: 16278403. 17: Taori K, Liu Y, Paul VJ, Luesch H. Combinatorial strategies by marine cyanobacteria: symplostatin 4, an antimitotic natural dolastatin 10/15 hybrid that synergizes with the coproduced HDAC inhibitor largazole. Chembiochem. 2009 Jul 6;10(10):1634-9. doi: 10.1002/cbic.200900192. PubMed PMID: 19514039. 18: Aherne GW, Hardcastle A, Valenti M, Bryant A, Rogers P, Pettit GR, Srirangam JK, Kelland LR. Antitumour evaluation of dolastatins 10 and 15 and their measurement in plasma by radioimmunoassay. Cancer Chemother Pharmacol. 1996;38(3):225-32. PubMed PMID: 8646796. 19: Mita AC, Hammond LA, Bonate PL, Weiss G, McCreery H, Syed S, Garrison M, Chu QS, DeBono JS, Jones CB, Weitman S, Rowinsky EK. Phase I and pharmacokinetic study of tasidotin hydrochloride (ILX651), a third-generation dolastatin-15 analogue, administered weekly for 3 weeks every 28 days in patients with advanced solid tumors. Clin Cancer Res. 2006 Sep 1;12(17):5207-15. PubMed PMID: 16951240. 20: Beckwith M, Urba WJ, Longo DL. Growth inhibition of human lymphoma cell lines by the marine products, dolastatins 10 and 15. J Natl Cancer Inst. 1993 Mar 17;85(6):483-8. PubMed PMID: 8445676.

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