Tetrocarcin A | 73666-84-9 | antitumor antibiotics| MedKoo

MedKoo Cat#: 581286 | Name: Tetrocarcin A

Description:

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

Tetrocarcin A is from cultures of strain No. T-90 designated as Micromonospora chalcea KY11091. Tetrocarcin has bacteriocidal activity against Bacillus subtilis, is new antitumor antibiotics.

Chemical Structure

Tetrocarcin A

CAS#73666-84-9

Theoretical Analysis

MedKoo Cat#: 581286

Name: Tetrocarcin A

CAS#: 73666-84-9

Chemical Formula: C54H72N2O182

Exact Mass: 1036.4780

Molecular Weight: 1037.17

Elemental Analysis: C, 62.54; H, 7.00; N, 2.70; O, 27.77

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

Tetrocarcin A; DC-11; Antlermicin A; Antibiotic DC 11;

IUPAC/Chemical Name

IUPAC Name: (1S,3S,4S,4aS,6aS,7Z,10S,11E,12aR,13S,20aS,20bR)-15-Formyl-13,18-dihydroxy-1,3,7,11,20a-pentamethyl-20,21-dioxo-10-({2,3,4,6-tetradeoxy-4-[(methoxycarbonyl)amino]-3-methyl-3-nitro-beta-D-xylo-hexopyra nosyl}oxy)-1,2,3,4,4a,6a,9,10,12a,13,14,20,20a,20b-tetradecahydro-16a,19-methanobenzo[b]naphtho[2,1-j]oxacyclotetradecin-4-yl 4-O-acetyl-2,6-dideoxy-3-O-[(2S,5R,6S)-5-({2,6-dideoxy-4-O-[(2S,5R,6S)-5-h ydroxy-6-methyltetrahydro-2H-pyran-2-yl]-alpha-L-ribo-hexopyranosyl}oxy)-6-methyltetrahydro-2H-pyran-2-yl]-alpha-L-ribo-hexopyranoside

InChi Key

ADRKQFXFMTYGSI-HCQSHQBASA-N

InChi Code

InChI=1S/C67H96N2O24/c1-30-14-18-47(88-54-28-65(11,69(79)80)60(38(9)86-54)68-64(78)81-13)31(2)23-43-45(73)24-40(29-70)27-67(43)62(76)55(63(77)93-67)61(75)66(12)42(30)16-15-41-56(66)32(3)22-33(4)57(41)92-53-26-49(59(37(8)85-53)87-39(10)71)90-50-21-19-48(35(6)83-50)89-52-25-46(74)58(36(7)84-52)91-51-20-17-44(72)34(5)82-51/h14-16,23,27,29,32-38,41-54,56-60,72-74,76H,17-22,24-26,28H2,1-13H3,(H,68,78)/b30-14-,31-23+/t32-,33-,34-,35-,36-,37-,38+,41-,42-,43+,44+,45-,46+,47-,48+,49+,50-,51-,52-,53-,54-,56+,57-,58-,59-,60-,65-,66+,67?/m0/s1

SMILES Code

C[C@H]1C[C@H](C)[C@H](O[C@H]2C[C@@H](O[C@H]3CC[C@@H](O[C@H]4C[C@@H](O)[C@@H](O[C@H]5CC[C@@H](O)[C@H](C)O5)[C@H](C)O4)[C@H](C)O3)[C@@H](OC(C)=O)[C@H](C)O2)[C@@H]6[C@@H]1[C@@]7(C)[C@H](/C(C)=C\C[C@H](O[C@H]8C[C@](C)([N+]([O-])=O)[C@@H](NC(OC)=O)[C@@H](C)O8)/C(C)=C/[C@@H]9[C@@H](O)CC(C=O)=CC9%10C(O)=C(C(O%10)=O)C7=O)C=C6

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 1,037.17 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: Gong T, Zhen X, Li XL, Chen JJ, Chen TJ, Yang JL, Zhu P. Tetrocarcin Q, a New Spirotetronate with a Unique Glycosyl Group from a Marine-Derived Actinomycete Micromonospora carbonacea LS276. Mar Drugs. 2018 Feb 24;16(2). pii: E74. doi: 10.3390/md16020074. PubMed PMID: 29495293; PubMed Central PMCID: PMC5852502. 2: Gui C, Zhang S, Zhu X, Ding W, Huang H, Gu YC, Duan Y, Ju J. Antimicrobial Spirotetronate Metabolites from Marine-Derived Micromonospora harpali SCSIO GJ089. J Nat Prod. 2017 May 26;80(5):1594-1603. doi: 10.1021/acs.jnatprod.7b00176. Epub 2017 May 10. PubMed PMID: 28489382. 3: Bruender NA, Holden HM. Probing the catalytic mechanism of a C-3'-methyltransferase involved in the biosynthesis of D-tetronitrose. Protein Sci. 2012 Jun;21(6):876-86. doi: 10.1002/pro.2074. Epub 2012 Apr 24. PubMed PMID: 22495991; PubMed Central PMCID: PMC3403422. 4: Kubiak RL, Holden HM. Combined structural and functional investigation of a C-3''-ketoreductase involved in the biosynthesis of dTDP-L-digitoxose. Biochemistry. 2011 Jul 5;50(26):5905-17. doi: 10.1021/bi200514b. Epub 2011 Jun 8. PubMed PMID: 21598943. 5: Bruender NA, Thoden JB, Kaur M, Avey MK, Holden HM. Molecular architecture of a C-3'-methyltransferase involved in the biosynthesis of D-tetronitrose. Biochemistry. 2010 Jul 20;49(28):5891-8. doi: 10.1021/bi100782b. PubMed PMID: 20527922. 6: Fang J, Zhang Y, Huang L, Jia X, Zhang Q, Zhang X, Tang G, Liu W. Cloning and characterization of the tetrocarcin A gene cluster from Micromonospora chalcea NRRL 11289 reveals a highly conserved strategy for tetronate biosynthesis in spirotetronate antibiotics. J Bacteriol. 2008 Sep;190(17):6014-25. doi: 10.1128/JB.00533-08. Epub 2008 Jun 27. PubMed PMID: 18586939; PubMed Central PMCID: PMC2519530. 7: Nakajima H, Sakaguchi K, Fujiwara I, Mizuta M, Tsuruga M, Magae J, Mizuta N. Apoptosis and inactivation of the PI3-kinase pathway by tetrocarcin A in breast cancers. Biochem Biophys Res Commun. 2007 Apr 27;356(1):260-5. Epub 2007 Mar 2. PubMed PMID: 17350598. 8: Hara T, Omura-Minamisawa M, Chao C, Nakagami Y, Ito M, Inoue T. Bcl-2 inhibitors potentiate the cytotoxic effects of radiation in Bcl-2 overexpressing radioresistant tumor cells. Int J Radiat Oncol Biol Phys. 2005 Feb 1;61(2):517-28. PubMed PMID: 15667975. 9: Anether G, Tinhofer I, Senfter M, Greil R. Tetrocarcin-A--induced ER stress mediates apoptosis in B-CLL cells via a Bcl-2--independent pathway. Blood. 2003 Jun 1;101(11):4561-8. Epub 2003 Jan 30. PubMed PMID: 12560233. 10: Tinhofer I, Anether G, Senfter M, Pfaller K, Bernhard D, Hara M, Greil R. Stressful death of T-ALL tumor cells after treatment with the anti-tumor agent Tetrocarcin-A. FASEB J. 2002 Aug;16(10):1295-7. Epub 2002 Jun 7. PubMed PMID: 12060673. 11: Kaneko M, Nakashima T, Uosaki Y, Hara M, Ikeda S, Kanda Y. Synthesis of tetrocarcin derivatives with specific inhibitory activity towards Bcl-2 functions. Bioorg Med Chem Lett. 2001 Apr 9;11(7):887-90. PubMed PMID: 11294384. 12: Igarashi Y, Takagi K, Kan Y, Fujii K, Harada K, Furumai T, Oki T. Arisostatins A and B, new members of tetrocarcin class of antibiotics from Micromonospora sp. TP-A0316. II. Structure determination. J Antibiot (Tokyo). 2000 Mar;53(3):233-40. PubMed PMID: 10819293. 13: Furumai T, Takagi K, Igarashi Y, Saito N, Oki T. Arisostatins A and B, new members of tetrocarcin class of antibiotics from Micromonospora sp. TP-A0316. I. Taxonomy, fermentation, isolation and biological properties. J Antibiot (Tokyo). 2000 Mar;53(3):227-32. PubMed PMID: 10819292. 14: Nakashima T, Miura M, Hara M. Tetrocarcin A inhibits mitochondrial functions of Bcl-2 and suppresses its anti-apoptotic activity. Cancer Res. 2000 Mar 1;60(5):1229-35. PubMed PMID: 10728681. 15: Namikawa K, Sakuma Y, Sunaga F, Kanno Y. Additive effects of tetrocarcin-A and diminazene aceturate concurrently administered against Babesia rodhaini-inoculated mice. Nihon Juigaku Zasshi. 1988 Aug;50(4):968-70. PubMed PMID: 3172611. 16: Namikawa K, Sakuma Y, Sunaga F, Kanno Y. Characteristics of tetrocarcin-A compared with other anti-piroplasmotic drugs. Nihon Juigaku Zasshi. 1988 Jun;50(3):605-12. PubMed PMID: 3210474. 17: Ohtomo M, Yamazaki K, Ito S, Shimura K, Shimizu S, Minami T, Fujinaga T, Shimada K. Effects of tetrocarcin-A on bovine theileriosis in Japan. Nihon Juigaku Zasshi. 1985 Aug;47(4):581-7. PubMed PMID: 4046263. 18: Tamaoki T, Tomita F. Biosynthesis of tetrocarcin. Incorporation of 14C- and 13C-labeled compounds into tetrocarcin. J Antibiot (Tokyo). 1983 May;36(5):595-8. PubMed PMID: 6874575. 19: Morimoto M, Fukui M, Ohkubo S, Tamaoki T, Tomita F. Tetrocarcins, new antitumor antibiotics. 3. Antitumor activity of tetrocarcin A. J Antibiot (Tokyo). 1982 Aug;35(8):1033-7. PubMed PMID: 7142004. 20: Tomita F, Tamaoki T. Tetrocarcins, novel antitumor antibiotics. I. Producing organism, fermentation and antimicrobial activity. J Antibiot (Tokyo). 1980 Sep;33(9):940-5. PubMed PMID: 6893706.