100940-65-6

Basic information

• Product Name: sandramycin
• Synonyms: sandramycin
• CAS NO: 100940-65-6
• Molecular Formula: C60H76N12O16
• Molecular Weight: 1221.33
• Product Categories: Antibiotic
• Mol File: 100940-65-6.mol

Chemical Properties

• Boiling Point: 1518.4°C at 760 mmHg
• Flash Point: 872.1°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.659
• Solubility: Soluble in DMSO
• CAS DataBase Reference: sandramycin(CAS DataBase Reference)
• NIST Chemistry Reference: sandramycin(100940-65-6)
• EPA Substance Registry System: sandramycin(100940-65-6)

Safety Data

• Hazardous Substances Data: 100940-65-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Sandramycin is used as an antitumor agent for its potent antitumor activity. It targets and intercalates DNA, disrupting cellular processes and inhibiting tumor growth.
Used in Antibacterial Applications:
Sandramycin is used as a potent antibacterial agent, effective against various bacterial strains. Its ability to intercalate DNA also contributes to its antibacterial properties, making it a valuable compound in the fight against bacterial infections.

Biological Activity

sandramycin is a cyclic depsipeptide antibiotic that was first isolated from cultured broth of a nocardioides sp [1].sandramycin is an antitumor antibiotic. sandramycin was closely related to the cyclic depsipeptides luzopeptins a, b, c and d. sandramycin exhibited strong inhibition to the gram-positive organisms bacillus subtilis, staphylococcus aureus and streptococcusfaecalis. its antimicrobial activity paralleled that which was observed for echinomycin and luzopeptin a [1]. sandramycin was also a bifunctional dna intercalator that strongly binds dna and forms crosslinks between dna molecules [2].in transplantable mouse leukemia p388, sandramycin was moderately active with values comparable to those for luzopeptin a. injection of 2 mg/kg showed the best increase in life span over the controls (61%) [1].

references

[1]. 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.[2]. 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.

InChI:InChI=1/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

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Related news

DNA binding properties of key sandramycin (cas 100940-65-6) analogues: systematic examination of the intercalation chromophore08/16/2019

The examination of a key series of chromophore analogues of sandramycin (1) is detailed employing surface plasmon resonance to establish binding constants within a single high affinity bis-intercalation binding site 5′-d(GCATGC)2, and to establish the preference for sandramycin binding to 5′-d...detailed

Synthesis of key sandramycin (cas 100940-65-6) analogs: systematic examination of the intercalation chromophore08/15/2019

The preparation and examination of 2–22 constituting a systematic study of the chromophore of sandramycin (1) are detailed. Fluorescence quenching studies were used to establish binding constants for 1–24 within calf thymus DNA, within a single high affinity bis-intercalation binding site 5′-...detailed

Relevant articles and documents

Total synthesis of sandramycin and its analogues via a multicomponent assemblage

The total synthesis of sandramycin has been accomplished by using a Staudinger/aza-Wittig/diastereoselective Ugi three-component reaction sequence as a key step to obtain a linear pentadepsipeptide. Subsequent [5 + 5] coupling of the penptapeptide, macrolactamization, and introduction of the quinaldin chromophores afforded sandramycin. Dihydroxy and diacetoxy analogues were also prepared, and the cytotoxic activity of these analogues against a range of human cancer cell lines was evaluated.

(-)-Sandramycin: Total synthesis and characterization of DNA binding properties

Full details of the total synthesis of the potent antitumor antibiotic (-)-sandramycin (1), a cyclic decadepsipeptide possessing a 2-fold axis of symmetry, is described and constitutes the first total synthesis of a member of the growing class of naturall