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MedKoo Cat#: 112151 | Name: Sandramycin
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Description:

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

Sandramycin is a cyclic depsipeptide antibiotic that is active against Gram-positive bacteria in vitro and leukemia P388 tumors in mice. Sandramycin has been investigated as an antibody drug conjugate (ADC) payload.

Chemical Structure

Sandramycin
Sandramycin
CAS# 100940-65-6

Theoretical Analysis

MedKoo Cat#: 112151

Name: Sandramycin

CAS#: 100940-65-6

Chemical Formula: C60H76N12O16

Exact Mass: 1220.5502

Molecular Weight: 1221.34

Elemental Analysis: C, 59.01; H, 6.27; N, 13.76; O, 20.96

Price and Availability

Size Price Availability Quantity
1mg USD 650.00 2 Weeks
5mg USD 1,650.00 2 Weeks
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Related CAS #
No Data
Synonym
Sandramycin; (-)-Sandramycin
IUPAC/Chemical Name
N,N'-((7R,11S,19aS,26R,30S,38aS)-11,30-diisopropyl-12,15,31,34-tetramethyl-6,10,13,16,19,25,29,32,35,38-decaoxodotriacontahydro-2H,6H,10H,25H-dipyrido[2,1-b1:2',1'-l][1,17]dioxa[4,7,10,13,20,23,26,29]octaazacyclodotriacontine-7,26-diyl)bis(3-hydroxyquinoline-2-carboxamide)
InChi Key
WXIVYIYCEBUEHL-RTQGILJWSA-N
InChi Code
InChI=1S/C60H76N12O16/c1-33(2)51-59(85)87-31-39(65-55(81)49-43(73)25-35-17-9-11-19-37(35)63-49)57(83)71-23-15-13-21-41(71)53(79)62-28-46(76)68(6)30-48(78)70(8)52(34(3)4)60(86)88-32-40(66-56(82)50-44(74)26-36-18-10-12-20-38(36)64-50)58(84)72-24-16-14-22-42(72)54(80)61-27-45(75)67(5)29-47(77)69(51)7/h9-12,17-20,25-26,33-34,39-42,51-52,73-74H,13-16,21-24,27-32H2,1-8H3,(H,61,80)(H,62,79)(H,65,81)(H,66,82)/t39-,40-,41+,42+,51+,52+/m1/s1
SMILES Code
O=C(N1CCCC[C@]1(C(NCC(N(C)CC(N(C)[C@@H](C(C)C)C(OC[C@H]2NC(C3=NC4=C(C=C3O)C=CC=C4)=O)=O)=O)=O)=O)[H])[C@H](NC(C5=NC6=C(C=C5O)C=CC=C6)=O)COC([C@H](C(C)C)N(C)C(CN(C)C(CNC([C@]7([H])CCCCN7C2=O)=O)=O)=O)=O
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,221.34 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
1: Petersen ME, Brant MG, Lasalle M, Fung VKC, Rojas AH, Wong J, Das S, Barnscher SD, Rich JR, Winters GC. Structure-Activity Relationships of Bis- Intercalating Peptides and Their Application as Antibody-Drug Conjugate Payloads. J Med Chem. 2023 Jun 22;66(12):8288-8309. doi: 10.1021/acs.jmedchem.3c00760. Epub 2023 Jun 12. PMID: 37307297. 2: Gade P, Erlandson A, Ullah A, Chen X, Mathews II, Mera PE, Kim CY. Structural and functional analyses of the echinomycin resistance conferring protein Ecm16 from Streptomyces lasalocidi. Sci Rep. 2023 May 17;13(1):7980. doi: 10.1038/s41598-023-34437-9. PMID: 37198233; PMCID: PMC10192343. 3: Sánchez-Hidalgo M, García MJ, González I, Oves-Costales D, Genilloud O. Complete Genome Sequence Analysis of Kribbella sp. CA-293567 and Identification of the Kribbellichelins A & B and Sandramycin Biosynthetic Gene Clusters. Microorganisms. 2023 Jan 19;11(2):265. doi: 10.3390/microorganisms11020265. PMID: 36838228; PMCID: PMC9962454. 4: Komatani Y, Momosaki K, Katsuyama A, Yamamoto K, Kaguchi R, Ichikawa S. Solid-Phase Total Synthesis of Sandramycin and Its Analogues. Org Lett. 2023 Jan 27;25(3):543-548. doi: 10.1021/acs.orglett.2c04327. Epub 2023 Jan 18. PMID: 36652724. 5: Virués-Segovia JR, Reyes F, Ruíz S, Martín J, Fernández-Pastor I, Justicia C, de la Cruz M, Díaz C, Mackenzie TA, Genilloud O, González I, Tormo JR. Kribbellichelins A and B, Two New Antibiotics from Kribbella sp. CA-293567 with Activity against Several Human Pathogens. Molecules. 2022 Sep 26;27(19):6355. doi: 10.3390/molecules27196355. PMID: 36234892; PMCID: PMC9570599. 6: Katayama K, Okamura T, Sunadome T, Nakagawa K, Takeda H, Shiro M, Matsuda A, Ichikawa S. Synthesis and biological evaluation of quinaldopeptin. J Org Chem. 2014 Mar 21;79(6):2580-90. doi: 10.1021/jo500039d. Epub 2014 Mar 13. PMID: 24555872. 7: Katayama K, Nakagawa K, Takeda H, Matsuda A, Ichikawa S. Total synthesis of sandramycin and its analogues via a multicomponent assemblage. Org Lett. 2014 Jan 17;16(2):428-31. doi: 10.1021/ol403319m. Epub 2013 Dec 17. PMID: 24341513. 8: Verma RP, Hansch C. Investigation of DNA-binding properties of organic molecules using quantitative structure-activity relationship (QSAR) models. J Pharm Sci. 2008 Jan;97(1):88-110. doi: 10.1002/jps.21087. PMID: 17722103. 9: Dawson S, Malkinson JP, Paumier D, Searcey M. Bisintercalator natural products with potential therapeutic applications: isolation, structure determination, synthetic and biological studies. Nat Prod Rep. 2007 Feb;24(1):109-26. doi: 10.1039/b516347c. Epub 2006 Nov 13. PMID: 17268609. 10: Hu J, Zhang C, Na R, Li Y. [A actinomycete strain C3905 producing antitumor antibiotic sandramycin from Antarctica]. Wei Sheng Wu Xue Bao. 2000 Dec;40(6):646-51. Chinese. PMID: 12549061. 11: Boger DL, Saionz KW. DNA binding properties of key sandramycin analogues: systematic examination of the intercalation chromophore. Bioorg Med Chem. 1999 Feb;7(2):315-21. doi: 10.1016/s0968-0896(98)00206-5. PMID: 10218823. 12: Boger DL, Chen JH, Saionz KW, Jin Q. Synthesis of key sandramycin analogs: systematic examination of the intercalation chromophore. Bioorg Med Chem. 1998 Jan;6(1):85-102. doi: 10.1016/s0968-0896(97)10014-1. PMID: 9502108. 13: Matson JA, Colson KL, Belofsky GN, Bleiberg BB. Sandramycin, a novel antitumor antibiotic produced by a Nocardioides sp. II. Structure determination. J Antibiot (Tokyo). 1993 Jan;46(1):162-6. doi: 10.7164/antibiotics.46.162. PMID: 8436549. 14: Matson JA, Bush JA. Sandramycin, a novel antitumor antibiotic produced by a Nocardioides sp. Production, isolation, characterization and biological properties. J Antibiot (Tokyo). 1989 Dec;42(12):1763-7. doi: 10.7164/antibiotics.42.1763. PMID: 2621159.

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