C 1027 | CAS# 120177-69-7 | enediyne antitumor antibiotic

MedKoo Cat#: 412199 | Name: C 1027

Description:

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

C 1027 or Lidamycin is an antitumor antibiotic consisting of a complex of an enediyne chromophore and an apoprotein. It shows antibiotic activity against most Gram-positive bacteria.It is one of the most potent cytotoxic molecules known, due to its induction of a higher ratio of DNA double-strand breaks than single-strand breaks.

Chemical Structure

C 1027

CAS#120177-69-7

Theoretical Analysis

MedKoo Cat#: 412199

Name: C 1027

CAS#: 120177-69-7

Chemical Formula: C44H51ClN3O13

Exact Mass: 864.3110

Molecular Weight: 865.35

Elemental Analysis: C, 61.07; H, 5.94; Cl, 4.10; N, 4.86; O, 24.04

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

C 1027; C1027; C-1027

IUPAC/Chemical Name

Antibiotic C-1027

InChi Key

XHGWHAHJQFXEOC-NKXFEUELSA-N

InChi Code

InChI=1S/C44H51ClN3O13/c1-23-40(53)47-35-27(19-26(55-6)20-31(35)57-23)41(54)58-32-22-56-34(50)21-29(46)25-17-28(45)38(30(49)18-25)59-33-13-9-11-24(32)12-10-16-44(33,14-7-8-15-44)61-42-37(52)36(51)39(48(4)5)43(2,3)60-42/h7-8,11,14-15,19-20,25,28-30,32-33,36-39,42,49,51-52H,1,16-18,21-22,46H2,2-6H3,(H,47,53)/b24-11-/t25?,28?,29-,30?,32-,33+,36-,37+,38?,39-,42-/m0/s1

SMILES Code

COc1cc(C(O[C@H]2COC(C[C@@H](C3CC(C(C(C3)Cl)O[C@@H]4C#C/C=C2/C#CCC45(C=CC=C5)O[C@@H]6OC(C)([C@@H](N(C)C)[C@H]([C@H]6O)O)C)O)N)=O)=O)c7c(OC(C(N7)=O)=C)c1

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

C-1027's chromophore contains a nine-membered enediyne that is responsible for most of the molecule's biological activity. Unlike other enediynes, this molecule contains no triggering mechanism. It is already primed to undergo the cycloaromatization reaction without external activation to produce the toxic 1,4-benzenoid diradical species. C-1027 can induce oxygen-independent interstrand DNA crosslinks in addition to the oxygen-dependent single- and double-stranded DNA breaks typically generated by other enediynes. This unique oxygen-independent mechanism suggests that C-1027 may be effective against hypoxic tumor cells. C-1027 shows promise as an anticancer drug and is currently undergoing phase II clinical trials in China, with a 30% success rate. It can induce apoptosis in many cancer cells and recent studies have indicated that it induces unusual DNA damage responses to double-strand breaks, including altering cell cycle progression and inducing chromosomal aberrations.

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 865.35 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: Sheng W, Geng J, Li L, Shang Y, Jiang M, Zhen Y. An albumin‑binding domain and targeting peptide‑based recombinant protein and its enediyne‑integrated analogue exhibit directional delivery and potent inhibitory activity on pancreatic cancer with K‑ras mutation. Oncol Rep. 2020 Mar;43(3):851-863. doi: 10.3892/or.2020.7468. Epub 2020 Jan 15. PMID: 32020213; PMCID: PMC7041235. 2: Cao R, Song W, Ye C, Liu X, Li L, Li Y, Yao H, Zhou X, Li L, Shao R. Internal enhancement of DNA damage by a novel bispecific antibody-drug conjugate-like therapeutics via blockage of mTOR and PD-L1 signal pathways in pancreatic cancer. Cancer Med. 2019 Feb;8(2):643-655. doi: 10.1002/cam4.1974. Epub 2019 Jan 25. PMID: 30681288; PMCID: PMC6382721. 3: Zhang C, Guo LY, Mu D, Gong JH, Chen J. Induction of apoptosis and erythroid differentiation of human chronic myelogenous leukemia K562 cells by low concentrations of lidamycin. Oncol Rep. 2019 Jan;41(1):475-482. doi: 10.3892/or.2018.6849. Epub 2018 Nov 2. PMID: 30542729. 4: Teijaro CN, Adhikari A, Shen B. Challenges and opportunities for natural product discovery, production, and engineering in native producers versus heterologous hosts. J Ind Microbiol Biotechnol. 2019 Mar;46(3-4):433-444. doi: 10.1007/s10295-018-2094-5. Epub 2018 Nov 13. PMID: 30426283; PMCID: PMC6405299. 5: Li L, Hu L, Zhao CY, Zhang SH, Wang R, Li Y, Shao RG, Zhen YS. The Recombinant and Reconstituted Novel Albumin-Lidamycin Conjugate Shows Lasting Tumor Imaging and Intensively Enhanced Therapeutic Efficacy. Bioconjug Chem. 2018 Sep 19;29(9):3104-3112. doi: 10.1021/acs.bioconjchem.8b00456. Epub 2018 Aug 23. PMID: 30105903. 6: Liu WJ, Liu XJ, Xu J, Li L, Li Y, Zhang SH, Wang JL, Miao QF, Zhen YS. EGFR- targeting, β-defensin-tailored fusion protein exhibits high therapeutic efficacy against EGFR-expressed human carcinoma via mitochondria-mediated apoptosis. Acta Pharmacol Sin. 2018 Nov;39(11):1777-1786. doi: 10.1038/s41401-018-0069-8. Epub 2018 Jul 16. PMID: 30013033; PMCID: PMC6289343. 7: Wang X, Sheng W, Wang Y, Li L, Li Y, Zhang S, Liu X, Chen S, Zhen Y. A Macropinocytosis-Intensifying Albumin Domain-Based scFv Antibody and Its Conjugate Directed against K-Ras Mutant Pancreatic Cancer. Mol Pharm. 2018 Jun 4;15(6):2403-2412. doi: 10.1021/acs.molpharmaceut.8b00234. Epub 2018 May 23. PMID: 29757658. 8: Chang CY, Lohman JR, Huang T, Michalska K, Bigelow L, Rudolf JD, Jedrzejczak R, Yan X, Ma M, Babnigg G, Joachimiak A, Phillips GN Jr, Shen B. Structural Insights into the Free-Standing Condensation Enzyme SgcC5 Catalyzing Ester-Bond Formation in the Biosynthesis of the Enediyne Antitumor Antibiotic C-1027. Biochemistry. 2018 Jun 12;57(23):3278-3288. doi: 10.1021/acs.biochem.8b00174. Epub 2018 Mar 21. PMID: 29533601; PMCID: PMC6219380. 9: Casini A, Chang FY, Eluere R, King AM, Young EM, Dudley QM, Karim A, Pratt K, Bristol C, Forget A, Ghodasara A, Warden-Rothman R, Gan R, Cristofaro A, Borujeni AE, Ryu MH, Li J, Kwon YC, Wang H, Tatsis E, Rodriguez-Lopez C, O'Connor S, Medema MH, Fischbach MA, Jewett MC, Voigt C, Gordon DB. A Pressure Test to Make 10 Molecules in 90 Days: External Evaluation of Methods to Engineer Biology. J Am Chem Soc. 2018 Mar 28;140(12):4302-4316. doi: 10.1021/jacs.7b13292. Epub 2018 Mar 16. PMID: 29480720. 10: Yan X, Hindra, Ge H, Yang D, Huang T, Crnovcic I, Chang CY, Fang SM, Annaval T, Zhu X, Huang Y, Zhao LX, Jiang Y, Duan Y, Shen B. Discovery of Alternative Producers of the Enediyne Antitumor Antibiotic C-1027 with High Titers. J Nat Prod. 2018 Mar 23;81(3):594-599. doi: 10.1021/acs.jnatprod.7b01013. Epub 2018 Jan 18. PMID: 29345939; PMCID: PMC6261254. 11: Wang R, Li L, Zhang S, Li Y, Wang X, Miao Q, Zhen Y. A novel enediyne- integrated antibody-drug conjugate shows promising antitumor efficacy against CD30+ lymphomas. Mol Oncol. 2018 Mar;12(3):339-355. doi: 10.1002/1878-0261.12166. Epub 2018 Jan 26. PMID: 29316337; PMCID: PMC5830626. 12: Annaval T, Rudolf JD, Chang CY, Lohman JR, Kim Y, Bigelow L, Jedrzejczak R, Babnigg G, Joachimiak A, Phillips GN Jr, Shen B. Crystal Structure of Thioesterase SgcE10 Supporting Common Polyene Intermediates in 9- and 10-Membered Enediyne Core Biosynthesis. ACS Omega. 2017 Aug 31;2(8):5159-5169. doi: 10.1021/acsomega.7b00933. Epub 2017 Aug 30. PMID: 28884166; PMCID: PMC5579567. 13: Cao HY, Guo XF, Zhu XF, Li SS, Zhen YS. A ligand-based and enediyne- energized bispecific fusion protein targeting epidermal growth factor receptor and insulin-like growth factor-1 receptor shows potent antitumor efficacy against esophageal cancer. Oncol Rep. 2017 Jun;37(6):3329-3340. doi: 10.3892/or.2017.5606. Epub 2017 Apr 27. PMID: 28498434. 14: Yan X, Ge H, Huang T, Hindra, Yang D, Teng Q, Crnovčić I, Li X, Rudolf JD, Lohman JR, Gansemans Y, Zhu X, Huang Y, Zhao LX, Jiang Y, Van Nieuwerburgh F, Rader C, Duan Y, Shen B. Strain Prioritization and Genome Mining for Enediyne Natural Products. mBio. 2016 Dec 20;7(6):e02104-16. doi: 10.1128/mBio.02104-16. PMID: 27999165; PMCID: PMC5181780. 15: Sha MQ, Zhao XL, Li L, Li LH, Li Y, Dong TG, Niu WX, Jia LJ, Shao RG, Zhen YS, Wang Z. EZH2 mediates lidamycin-induced cellular senescence through regulating p21 expression in human colon cancer cells. Cell Death Dis. 2016 Nov 24;7(11):e2486. doi: 10.1038/cddis.2016.383. PMID: 27882937; PMCID: PMC5260875. 16: Nishiwaki M, Takahara K, Matsumoto N. Arterial stiffness in young adult swimmers. Eur J Appl Physiol. 2017 Jan;117(1):131-138. doi: 10.1007/s00421-016-3505-9. Epub 2016 Nov 21. PMID: 27873019. 17: Huang T, Chang CY, Lohman JR, Rudolf JD, Kim Y, Chang C, Yang D, Ma M, Yan X, Crnovcic I, Bigelow L, Clancy S, Bingman CA, Yennamalli RM, Babnigg G, Joachimiak A, Phillips GN, Shen B. Crystal structure of SgcJ, an NTF2-like superfamily protein involved in biosynthesis of the nine-membered enediyne antitumor antibiotic C-1027. J Antibiot (Tokyo). 2016 Oct;69(10):731-740. doi: 10.1038/ja.2016.88. Epub 2016 Jul 13. PMID: 27406907; PMCID: PMC5083130. 18: Chang CY, Lohman JR, Cao H, Tan K, Rudolf JD, Ma M, Xu W, Bingman CA, Yennamalli RM, Bigelow L, Babnigg G, Yan X, Joachimiak A, Phillips GN Jr, Shen B. Crystal Structures of SgcE6 and SgcC, the Two-Component Monooxygenase That Catalyzes Hydroxylation of a Carrier Protein-Tethered Substrate during the Biosynthesis of the Enediyne Antitumor Antibiotic C-1027 in Streptomyces globisporus. Biochemistry. 2016 Sep 13;55(36):5142-54. doi: 10.1021/acs.biochem.6b00713. Epub 2016 Sep 1. PMID: 27560143; PMCID: PMC5024704. 19: Li W, Li X, Huang T, Teng Q, Crnovcic I, Rader C, Shen B. Engineered production of cancer targeting peptide (CTP)-containing C-1027 in Streptomyces globisporus and biological evaluation. Bioorg Med Chem. 2016 Sep 1;24(17):3887-3892. doi: 10.1016/j.bmc.2016.04.017. Epub 2016 Apr 8. PMID: 27094150; PMCID: PMC4972678. 20: Zhen Y, Shang B, Liu X, Lin Y, Zhen Y. Antitumor efficacy of lidamycin against human multiple myeloma RPMI 8226 cells and the xenograft in nonobese diabetic/severe combined immunodeficiency mice. J Cancer Res Ther. 2016 Jan- Mar;12(1):182-7. doi: 10.4103/0973-1482.146093. PMID: 27072234.