Gilvocarcin M | 77879-89-1 | antibiotic

MedKoo Cat#: 581288 | Name: Gilvocarcin M

Description:

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

Gilvocarcin M is an antibiotic originally isolated from S. gilvotanareus. Gilvocarcin M displays potent antibacterial, antifungal, antiviral and antitumor activity.

Chemical Structure

Gilvocarcin M

CAS#77879-89-1

Theoretical Analysis

MedKoo Cat#: 581288

Name: Gilvocarcin M

CAS#: 77879-89-1

Chemical Formula: C26H26O9

Exact Mass: 482.1577

Molecular Weight: 482.49

Elemental Analysis: C, 64.72; H, 5.43; O, 29.84

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Synonym

Gilvocarcin M; BRN 5675008; DC-38-M;

IUPAC/Chemical Name

6H-Benzo(d)naphtho(1,2-b)pyran-6-one, 4-(6-deoxy-alpha-galactofuranosyl)-1-hydroxy-10,12-dimethoxy-8-methyl-

InChi Key

BYFOTBZTKXSZHH-FUCVEXJHSA-N

InChi Code

InChI=1S/C26H26O9/c1-10-7-14-18(16(8-10)32-3)13-9-17(33-4)20-15(28)6-5-12(19(20)24(13)35-26(14)31)25-22(30)21(29)23(34-25)11(2)27/h5-9,11,21-23,25,27-30H,1-4H3/t11-,21-,22-,23+,25-/m1/s1

SMILES Code

O=C1C2=CC(C)=CC(OC)=C2C3=CC(OC)=C4C(O)=CC=C([C@@H]5[C@@H]([C@H]([C@H]([C@@H](C)O)O5)O)O)C4=C3O1

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 482.49 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: Tibrewal N, Pahari P, Wang G, Kharel MK, Morris C, Downey T, Hou Y, Bugni TS, Rohr J. Baeyer-Villiger C-C bond cleavage reaction in gilvocarcin and jadomycin biosynthesis. J Am Chem Soc. 2012 Nov 7;134(44):18181-4. doi: 10.1021/ja3081154. Epub 2012 Oct 29. PubMed PMID: 23102024; PubMed Central PMCID: PMC3498853. 2: Shepherd MD, Liu T, Méndez C, Salas JA, Rohr J. Engineered biosynthesis of gilvocarcin analogues with altered deoxyhexopyranose moieties. Appl Environ Microbiol. 2011 Jan;77(2):435-41. doi: 10.1128/AEM.01774-10. Epub 2010 Nov 12. PubMed PMID: 21075894; PubMed Central PMCID: PMC3020532. 3: James CA, Snieckus V. Combined directed remote metalation-transition metal catalyzed cross coupling strategies: the total synthesis of the aglycones of the gilvocarcins V, M, and E and arnottin I. J Org Chem. 2009 Jun 5;74(11):4080-93. doi: 10.1021/jo9001454. PubMed PMID: 19441800. 4: Liu T, Kharel MK, Zhu L, Bright SA, Mattingly C, Adams VR, Rohr J. Inactivation of the ketoreductase gilU gene of the gilvocarcin biosynthetic gene cluster yields new analogues with partly improved biological activity. Chembiochem. 2009 Jan 26;10(2):278-86. doi: 10.1002/cbic.200800348. PubMed PMID: 19067453; PubMed Central PMCID: PMC2680003. 5: Cordero-Vargas A, Quiclet-Sire B, Zard SZ. Model studies towards the synthesis of gilvocarcin M. Org Biomol Chem. 2005 Dec 21;3(24):4432-43. Epub 2005 Nov 16. PubMed PMID: 16327904. 6: Arce R, Oyola R, Alegría AE. The photobiological differences of gilvocarcins V and M are not related to their transient intermediates and triplet yields. Photochem Photobiol. 1998 Jul;68(1):25-31. PubMed PMID: 9679448. 7: Oyola R, Arce R, Alegría AE, García C. Photophysical properties of gilvocarcins V and M and their binding constant to calf thymus DNA. Photochem Photobiol. 1997 May;65(5):802-10. PubMed PMID: 9155255. 8: Alegría AE, Zayas L, Guevara N. A comparative study of the visible light photochemistry of gilvocarcins V and M. Photochem Photobiol. 1995 Sep;62(3):409-15. PubMed PMID: 8570700. 9: Nakajima S, Kojiri K, Suda H, Okanishi M. New antitumor substances, BE-12406A and BE-12406B, produced by a streptomycete. II. Structure determination. J Antibiot (Tokyo). 1991 Oct;44(10):1061-4. PubMed PMID: 1955387. 10: Frolova VI, Kuzovkov AD, Chernyshev AI. [Identification of antibiotics 1072A and 1072B as antibiotics of the toromycin group]. Antibiotiki. 1984 May;29(5):329-32. Russian. PubMed PMID: 6331291. 11: Elespuru RK, Gonda SK. Activation of antitumor agent gilvocarcins by visible light. Science. 1984 Jan 6;223(4631):69-71. PubMed PMID: 6229029. 12: Takahashi K, Tomita F. Gilvocarcins, new antitumor antibiotics. 5. Biosynthesis of gilvocarcins: incorporation of 13C-labeled compounds into gilvocarcin aglycones. J Antibiot (Tokyo). 1983 Nov;36(11):1531-5. PubMed PMID: 6418705. 13: Weiss U, Yoshihira K, Highet RJ, White RJ, Wei TT. The chemistry of the antibiotics chrysomycin A and B. Antitumor activity of chrysomycin A. J Antibiot (Tokyo). 1982 Sep;35(9):1194-201. PubMed PMID: 7142022. 14: Tomita F, Takahashi K, Tamaoki T. Gilvocarcins, new antitumor antibiotics. 4. Mode of action. J Antibiot (Tokyo). 1982 Aug;35(8):1038-41. PubMed PMID: 6815145. 15: Wei TT, Chan JA, Roller PP, Weiss U, Stroshane RM, White RJ, Byrne KM. Detection of gilvocarcin antitumor complex by a biochemical induction assay (BIA). J Antibiot (Tokyo). 1982 Apr;35(4):529-32. PubMed PMID: 7096209. 16: Balitz DM, O'Herron FA, Bush J, Vyas DM, Nettleton DE, Grulich RE, Bradner WT, Doyle TW, Arnold E, Clardy J. Antitumor agents from Streptomyces anandii: gilvocarcins V, M and E. J Antibiot (Tokyo). 1981 Dec;34(12):1544-55. PubMed PMID: 7344705. 17: Morimoto M, Okubo S, Tomita F, Marumo H. Gilvocarcins, new antitumor antibiotics. 3. Antitumor activity. J Antibiot (Tokyo). 1981 Jun;34(6):701-7. PubMed PMID: 6792176. 18: Takahashi K, Yoshida M, Tomita F, Shirahata K. Gilvocarcins, new antitumor antibiotics. 2. Structural elucidation. J Antibiot (Tokyo). 1981 Mar;34(3):271-5. PubMed PMID: 7275808. 19: Nakano H, Matsuda Y, Ito K, Ohkubo S, Morimoto M, Tomita F. Gilvocarcins, new antitumor antibiotics. 1. Taxonomy, fermentation, isolation and biological activities. J Antibiot (Tokyo). 1981 Mar;34(3):266-70. PubMed PMID: 7275807.