Sibiromycin
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MedKoo CAT#: 333083

CAS#: 12684-33-2

Description: Sibiromycin is a natural compound with antitumor activity. Sibiromycin is also a potent antitumor antibiotic that binds covalently to DNA in the minor groove at the NH2 of guanine.


Chemical Structure

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Sibiromycin
CAS# 12684-33-2

Theoretical Analysis

MedKoo Cat#: 333083
Name: Sibiromycin
CAS#: 12684-33-2
Chemical Formula: C24H33N3O7
Exact Mass: 475.2319
Molecular Weight: 475.542
Elemental Analysis: C, 60.62; H, 6.99; N, 8.84; O, 23.55

Price and Availability

Size Price Availability Quantity
5.0mg USD 1250.0 2 Weeks
10.0mg USD 2250.0 2 Weeks
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Synonym: Sibiromycin;

IUPAC/Chemical Name: 5H-Pyrrolo[2,1-c][1,4]benzodiazepin-5-one,7-[[4,6-dideoxy-3-C-methyl-4-(methylamino)-a-L-mannopyranosyl]oxy]-1,10,11,11a-tetrahydro-9,11-dihydroxy-8-methyl-2-(1E)-1-propen-1-yl-,(11R,11aS)-

InChi Key: RAGFPHFDFVNLCG-INYQBOQCSA-N

InChi Code: InChI=1S/C24H33N3O7/c1-6-7-13-8-15-21(30)26-17-14(22(31)27(15)10-13)9-16(11(2)18(17)28)34-23-20(29)24(4,32)19(25-5)12(3)33-23/h6-7,9-10,12,15,19-21,23,25-26,28-30,32H,8H2,1-5H3/b7-6+/t12-,15-,19-,20-,21+,23-,24+/m0/s1

SMILES Code: O=C1N2[C@](CC(/C=C/C)=C2)([H])[C@@H](O)NC3=C(O)C(C)=C(O[C@H]4[C@@H]([C@]([C@@H](NC)[C@H](C)O4)(C)O)O)C=C13

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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

Preparing Stock Solutions

The following data is based on the product molecular weight 475.542 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

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1: Kemp GC, Tiberghien AC, Patel NV, D'Hooge F, Nilapwar SM, Adams LR, Corbett S, Williams DG, Hartley JA, Howard PW. Synthesis and in vitro evaluation of SG3227, a pyrrolobenzodiazepine dimer antibody-drug conjugate payload based on sibiromycin. Bioorg Med Chem Lett. 2017 Mar 1;27(5):1154-1158. doi: 10.1016/j.bmcl.2017.01.074. Epub 2017 Jan 30. PMID: 28188066.

2: Saha S, Li W, Gerratana B, Rokita SE. Identification of the dioxygenase- generated intermediate formed during biosynthesis of the dihydropyrrole moiety common to anthramycin and sibiromycin. Bioorg Med Chem. 2015 Feb 1;23(3):449-54. doi: 10.1016/j.bmc.2014.12.024. Epub 2014 Dec 20. PMID: 25564379; PMCID: PMC4302019.

3: Jackson PJ, James CH, Jenkins TC, Rahman KM, Thurston DE. Computational studies support the role of the C7-sibirosamine sugar of the pyrrolobenzodiazepine (PBD) sibiromycin in transcription factor inhibition. ACS Chem Biol. 2014 Oct 17;9(10):2432-40. doi: 10.1021/cb5002203. Epub 2014 Aug 11. PMID: 25111266.

4: Yonemoto IT, Li W, Khullar A, Reixach N, Gerratana B. Mutasynthesis of a potent anticancer sibiromycin analogue. ACS Chem Biol. 2012 Jun 15;7(6):973-7. doi: 10.1021/cb200544u. Epub 2012 Mar 23. Erratum in: ACS Chem Biol. 2014 May 16;9(5):1214. PMID: 22390171; PMCID: PMC3376188.

5: Giessen TW, Kraas FI, Marahiel MA. A four-enzyme pathway for 3,5-dihydroxy-4-methylanthranilic acid formation and incorporation into the antitumor antibiotic sibiromycin. Biochemistry. 2011 Jun 28;50(25):5680-92. doi: 10.1021/bi2006114. Epub 2011 Jun 3. PMID: 21612226.

6: Sulc M, Fadrhoncová I, Jelínková M, Chudomelová M, Felsberg J, Olšovská J. Determination of sibiromycin and its natural derivatives using new analytical and structural approaches. J Chromatogr A. 2011 Jan 7;1218(1):83-91. doi: 10.1016/j.chroma.2010.10.110. Epub 2010 Nov 3. PMID: 21111423.

7: Li W, Khullar A, Chou S, Sacramo A, Gerratana B. Biosynthesis of sibiromycin, a potent antitumor antibiotic. Appl Environ Microbiol. 2009 May;75(9):2869-78. doi: 10.1128/AEM.02326-08. Epub 2009 Mar 6. PMID: 19270142; PMCID: PMC2681668.

8: Hu JL, Xie MY, Lu WY. [A new variety of Actinoplanes-producing sibiromycin]. Wei Sheng Wu Xue Bao. 1986 Mar;26(1):90-3. Chinese. PMID: 3604209.

9: Gairola C, Thomas H, Szeinbach SL, Lubawy WC. The genetic activity of anthramycin, tomaymycin and sibiromycin in bacterial forward- and reverse- mutation assays and in the mouse bone-marrow micronucleus test. J Appl Toxicol. 1983 Dec;3(6):317-20. doi: 10.1002/jat.2550030609. PMID: 6376603.

10: Petrusek RL, Anderson GL, Garner TF, Fannin QL, Kaplan DJ, Zimmer SG, Hurley LH. Pyrrol[1,4]benzodiazepine antibiotics. Proposed structures and characteristics of the in vitro deoxyribonucleic acid adducts of anthramycin, tomaymycin, sibiromycin, and neothramycins A and B. Biochemistry. 1981 Mar 3;20(5):1111-9. doi: 10.1021/bi00508a011. PMID: 6261786.

11: Koz'mian LI, Dudnik IuV, Zimmer C, Luck G. Nukleotidnaia spetsifichnost' vzaimodeĭstviia sibiromitsina s DNK [Nucleotide specificity of sibiromycin interaction with DNA]. Antibiotiki. 1980 Mar;25(3):210-5. Russian. PMID: 6987949.

12: Hurley LH, Lasswell WL, Ostrander JM, Parry R. Pyrrolo[1,4]benzodiazepine antibiotics. Biosynthetic conversion of tyrosine to the C2- and C3-proline moieties of anthramycin, tomaymycin, and sibiromycin. Biochemistry. 1979 Sep 18;18(19):4230-7. doi: 10.1021/bi00586a030. PMID: 582801.

13: Hurley LH, Lasswell WL, Malhotra RK, Das NV. Pyrrolo[1,4]benzodiazepine antibiotics. Biosynthesis of the antitumor antibiotic sibiromycin by Streptosporangium sibiricum. Biochemistry. 1979 Sep 18;18(19):4225-9. doi: 10.1021/bi00586a029. PMID: 582800.

14: Hurley LH, Gairola C. Pyrrolo (1,4) benzodiazepine antitumor antibiotics: Biosynthetic studies on the conversion of tryptophan to the anthranilic acid moieties of sibiromycin and tomaymycin. Antimicrob Agents Chemother. 1979 Jan;15(1):42-5. doi: 10.1128/AAC.15.1.42. PMID: 581831; PMCID: PMC352597.

15: Loz'mian LI. Vzaimodeĭstvie sibiromitsina s rastvorimym khromatinom iz kletok limfadenoza mysheĭ NK/LI [Interaction of sibiromycin with soluble chromatin from the cells of murine NK/LI lymphadenosis]. Antibiotiki. 1978 Nov;23(11):1015-7. Russian. PMID: 581439.

16: Koz'mian LI, Gauze GG, Galkin VI, Dudnik IuV. Issledovanie vzaimodeĭstviia sibiromitsina s lineĭnoĭ i kol'tsevoĭ DNK metodom ul'tratsentrifugirovaniia v gradientakh plotnosti [Density gradient ultracentrifugation method of studying sibiromycin interaction with linear and circular DNA]. Antibiotiki. 1978 Sep;23(9):771-5. Russian. PMID: 358909.

17: Koz'mian LI, Dudnik IuV, Shepelevtseva NG. Rol' funktsional'nykh grupp molekuly sibiromitsina v sviazyvanii s DNK [Role of the functional groups of the sibiromycin molecule in DNA binding]. Antibiotiki. 1977 Jul;22(7):602-6. Russian. PMID: 18983.

18: Hurley LH. Pyrrolo(1,4)benzodiazepine antitumor antibiotics. Comparative aspects of anthramycin, tomaymycin and sibiromycin. J Antibiot (Tokyo). 1977 May;30(5):349-70. doi: 10.7164/antibiotics.30.349. PMID: 328469.

19: Hurley LH, Gairola C, Zmijewski M. Pyrrolo(1,4)benzodiazepine antitumor antibiotics. In vitro interaction of anthramycin, sibiromycin and tomaymycin with DNA using specifically radiolabelled molecules. Biochim Biophys Acta. 1977 Apr 4;475(3):521-35. doi: 10.1016/0005-2787(77)90067-3. PMID: 15599.

20: Donua AK, Fedorova ZhE. Vliianie aktinomitsina D i sibiromitsina na vkliuchenie 3H-timidina na raznykh stadiiakh razvitiia Nereis virens Sars [Effect of actinomycin D and sibiromycin on 3H-thymidine incorporation into the early developmental stages of Nereis virens Sars]. Ontogenez. 1977;8(2):170-5. Russian. PMID: 578569.